Updated on 2024/08/05

写真a

 
SHINADA Tetsuro
 
Organization
Graduate School of Science Department of Chemistry Professor
School of Science Department of Chemistry
Title
Professor
Affiliation
Institute of Science

Position

  • Graduate School of Science Department of Chemistry 

    Professor  2022.04 - Now

  • School of Science Department of Chemistry 

    Professor  2022.04 - Now

Degree

  • Doctor of Pharmaceutical Science ( Kobe Pharmaceutical University )

Research Areas

  • Life Science / Bioorganic chemistry  / natural products chemistry

  • Life Science / Bioorganic chemistry  / Total synthesis

Research Interests

  • 天然物化学

  • 生物有機科学

  • Synthetic Studies of Natural Products

Research subject summary

  • 天然有機化合物を題材として、全合成研究およびケミカルバイオロジー研究を行っている。

Research Career

Professional Memberships

  • THE CHEMICAL SOCIETY OF JAPAN

      Domestic

  • 日本農芸化学会

    2020.03 - Now

  • 日本農芸化学会

      Domestic

  • 応用動物昆虫学会

      Domestic

  • 近畿化学協会

      Domestic

  • アメリカ化学会

      Overseas

  • 有機合成化学協会

      Domestic

  • 日本薬学会

      Domestic

  • 有機合成化学協会

  • 近畿化学協会

  • 日本薬学会

  • THE CHEMICAL SOCIETY OF JAPAN

  • アメリカ化学会

▼display all

Committee Memberships (off-campus)

  • 委員   第15回京都国際有機化学会議  

    2023.02 - 2023.12 

Awards

  • 第6回有機合成化学協会関西支部賞

    2008  

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    Country:Japan

  • 有機合成化学協会 令和元年度カネカ生命科学賞

    2019.12  

Job Career (off-campus)

  • 大阪公立大学   大学院理学研究科 化学専攻

    2022.04 - Now

  • Osaka City University   Graduate School of Science Molecular Materials Science Course

    2010.10 - 2022.03

  • サントリー生物有機科学研究所博士研究員   -

    1994 - 1996

  • テキサスA&M大学化学科博士客員研究員   -

    1992 - 1993

Education

  • Kobe Pharmaceutical University   Doctor's Course  

    - 1992

  • Setsunan University    

    - 1987

Papers

  • Total Synthesis of Bipenicilisorin and Assignment of the Absolute Configuration. Reviewed

    Eigo Fukuda, Ibuki Fujiwara, Shoki Maruno, Kaiki Motomura, Seiya Endo, Arihiro Iwasaki, Tatsuya Fukuta, Atsushi Nakayama, Tetsuro Shinada

    Journal of natural products   2024.05

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    Publishing type:Research paper (scientific journal)   International / domestic magazine:International journal  

    The first total synthesis of bipenicilisorin (1) isolated from Penicillium chrysogenum SCSIO 41001 via its monomer natural product, penicilisorin (2), was achieved. Penicilisorin was synthesized in four steps from a o-bromobenzaldehyde derivative via the Pd-catalyzed one-pot fluorocarbonylation/lactonization/β-elimination cascade reaction. Iodination of penicilisorin gave 7-iodopenicilisorin which was dimerized by Pd-catalyzed homodimerization to provide (±)-bipenicilisorin. The unknown absolute configuration of naturally occurring (+)-bipenicilisorin was examined by optical resolution of the (±)-synthetic bipenicilisorin and a comparison of experimental and theoretical electronic circular dichroism (ECD) spectra. These results support the absolute configuration of the natural product to be Sa. A cytotoxic activity test of (+)-and (-)-bipenicilisorin using A549 cells revealed that (+)-1 has a lower IC50 value than (-)-1.

    DOI: 10.1021/acs.jnatprod.4c00114

    PubMed

  • Identification of the Cirratiomycin Biosynthesis Gene Cluster in Streptomyces Cirratus: Elucidation of the Biosynthetic Pathways for 2,3-Diaminobutyric Acid and Hydroxymethylserine. Reviewed

    Shunki Sakata, Jiafeng Li, Yoko Yasuno, Tetsuro Shinada, Kazuo Shin-Ya, Yohei Katsuyama, Yasuo Ohnishi

    Chemistry (Weinheim an der Bergstrasse, Germany)   e202400271   2024.03

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    Publishing type:Research paper (scientific journal)   International / domestic magazine:International journal  

    Cirratiomycin, a heptapeptide with antibacterial activity, was isolated and characterized in 1981; however, its biosynthetic pathway has not been elucidated. It contains several interesting nonproteinogenic amino acids, such as (2S,3S)-2,3-diaminobutyric acid ((2S,3S)-DABA) and α-(hydroxymethyl)serine, as building blocks. Here, we report the identification of a cirratiomycin biosynthetic gene cluster in Streptomyces cirratus. Bioinformatic analysis revealed that several Streptomyces viridifaciens and Kitasatospora aureofaciens strains also have this cluster. One S. viridifaciens strain was confirmed to produce cirratiomycin. The biosynthetic gene cluster was shown to be responsible for cirratiomycin biosynthesis in S. cirratus in a gene inactivation experiment using CRISPR-cBEST. Interestingly, this cluster encodes a nonribosomal peptide synthetase (NRPS) composed of 12 proteins, including those with an unusual domain organization: a stand-alone adenylation domain, two stand-alone condensation domains, two type II thioesterases, and two NRPS modules that have no adenylation domain. Using heterologous expression and in vitro analysis of recombinant enzymes, we revealed the biosynthetic pathway of (2S,3S)-DABA: (2S,3S)-DABA is synthesized from l-threonine by four enzymes, CirR, CirS, CirQ, and CirB. In addition, CirH, a glycine/serine hydroxymethyltransferase homolog, was shown to synthesize α-(hydroxymethyl)serine from d-serine in vitro. These findings broaden our knowledge of nonproteinogenic amino acid biosynthesis.

    DOI: 10.1002/chem.202400271

    PubMed

  • First Total Syntheses of Beauvericin A and <i>allo</i>-Beauvericin A Reviewed

    Natsumi Kozakai, Seiya Endo, Atsushi Nakayama, Riku Horinouchi, Makoto Yoshida, Masayoshi Arai, Tetsuro Shinada

    ACS Omega   9 ( 10 )   12228 - 12236   2024.02( ISSN:2470-1343 ( eISSN:2470-1343

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acsomega.4c00278

  • Substrate-Dependent Alteration in the &lt;i&gt;C&lt;/i&gt;- and &lt;i&gt;O&lt;/i&gt;-Prenylation Specificities of &lt;i&gt;Cannabis&lt;/i&gt; Prenyltransferase Reviewed

    Ryosuke Tanaya, Takeshi Kodama, Juthamart Maneenet, Yoko Yasuno, Atsushi Nakayama, Tetsuro Shinada, Hironobu Takahashi, Takuya Ito, Hiroyuki Morita, Suresh Awale, Futoshi Taura

    Biological and Pharmaceutical Bulletin   47 ( 2 )   449 - 453   2024.02( ISSN:0918-6158 ( eISSN:1347-5215

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1248/bpb.b23-00868

  • Analysis of vitamin D receptor binding affinities of enzymatically synthesized triterpenes including ambrein and unnatural onoceroids. Reviewed

    Daijiro Ueda, Natsu Matsuda, Yuka Takaba, Nami Hirai, Mao Inoue, Taichi Kameya, Tohru Abe, Nao Tagaya, Yasuhiro Isogai, Yoshito Kakihara, Florian Bartels, Mathias Christmann, Tetsuro Shinada, Kaori Yasuda, Tsutomu Sato

    Scientific reports   14 ( 1 )   1419 - 1419   2024.01

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    Publishing type:Research paper (scientific journal)   International / domestic magazine:International journal  

    Onoceroids are a rare family of triterpenes. One representative onoceroid is ambrein, which is the main component of ambergris used as a traditional medicine. We have previously identified the onoceroid synthase, BmeTC, in Bacillus megaterium and succeeded in creating ambrein synthase by introducing mutations into BmeTC. Owing to the structural similarity of ambrein to vitamin D, a molecule with diverse biological activities, we hypothesized that some of the activities of ambergris may be induced by the binding of ambrein to the vitamin D receptor (VDR). We demonstrated the VDR binding ability of ambrein. By comparing the structure-activity relationships of triterpenes with both the VDR affinity and osteoclastic differentiation-promoting activity, we observed that the activity of ambrein was not induced via the VDR. Therefore, some of the activities of ambergris, but not all, can be attributed to its VDR interaction. Additionally, six unnatural onoceroids were synthesized using the BmeTC reactions, and these compounds exhibited higher VDR affinity than that of ambrein. Enzymatic syntheses of onoceroid libraries will be valuable in creating a variety of bioactive compounds beyond ambergris.

    DOI: 10.1038/s41598-024-52013-7

    PubMed

  • Catalytic Potential of <i>Cannabis</i> Prenyltransferase to Expand Cannabinoid Scaffold Diversity Reviewed

    Ryosuke Tanaya, Takeshi Kodama, Yuan-E Lee, Yoko Yasuno, Tetsuro Shinada, Hironobu Takahashi, Takuya Ito, Hiroyuki Morita, Suresh Awale, Futoshi Taura

    Organic Letters   2023.11( ISSN:1523-7060 ( eISSN:1523-7052

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.orglett.3c03410

  • Concise Synthesis of Isocoumarin-3-carboxylic Acid Esters Reviewed

    Atsushi Nakayama, Kenichiro Hamamoto†, Ibuki Fujiwara†, Eigo Fukuda, Keita Ozawa, Seiya Endo, Rika Yamasaki, Hidemitsu Yamanaka, Yusaku Tamura, Yuki Yamamoto, Tetsuro Shinada

    Chemistry Letters   52   640 - 643   2023.06

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1246/cl.230219

  • Synthesis of Drimane-8α,11-diol Using Terpene Cyclase from <i>Bacillus megaterium</i> Reviewed

    Keita Ozawa, Yuki Yamamoto, Eigo Fukuda, Seiya Endo, Atsushi Nakayama, Yoko Yasuno, Daijiro Ueda, Tsutomu Sato, Tetsuro Shinada

    Chemistry Letters   52 ( 6 )   520 - 523   2023.05( ISSN:0366-7022 ( eISSN:1348-0715

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1246/cl.230151

  • Juvenile hormone identification in the cabbage bug <i>Eurydema rugosa</i> Reviewed

    Aya Kodama, Keiji Matsumoto, Tetsuro Shinada, Shin G. Goto

    Bulletin of Entomological Research   113 ( 3 )   293 - 298   2023.03( ISSN:0007-4853 ( eISSN:1475-2670

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    Publishing type:Research paper (scientific journal)  

    Abstract

    Juvenile hormone (JH) plays a pivotal role in almost every aspect of insect development and reproduction. The chemical structure of the JH in heteropteran species has long remained elusive until methyl (2R,3S,10R)-2,3;10,11-bisepoxyfarnesoate, commonly named as juvenile hormone III skipped bisepoxide (JHSB<sub>3</sub>), was isolated from Plautia stali (Hemiptera: Heteroptera: Pentatomidae). Recently, several groups reported the presence of JHSB<sub>3</sub> in other heteropteran species. However, most of the studies paid no attention to the determination of the relative and absolute structure of the JH. In this study, we investigated the JH of the cabbage bug Eurydema rugosa (Hemiptera: Heteroptera: Pentatomidae), known as a pest for wild and cultivated crucifers. JHSB<sub>3</sub> was detected in the hexane extract from the corpus allatum (CA) product using a chiral ultraperformance liquid chromatography-tandem mass spectrometer (UPLC-MS/MS) which can inform the absolute stereochemistry of the JH. Its stereoisomers were not detected. Topical application of the synthetic JHSB<sub>3</sub> to the last instar nymphs inhibited their metamorphosis and induced nymphal-type colouration of the dorsal abdomen in a dose-dependent manner. Additionally, the topical application of JHSB<sub>3</sub> effectively terminated summer and winter diapauses in females. These results indicate that the JH of E. rugosa is JHSB<sub>3</sub>. Although individuals in summer and winter diapauses are physiologically distinct in E. rugosa, the results suggest that the physiological differences between these diapauses are based, not on the responsiveness to JH, but on the processes governing activation of the CA or on its upstream cascades.

    DOI: 10.1017/s0007485321000158

  • Mechanisms of Sugar Aminotransferase-like Enzymes to Synthesize Stereoisomers of Non-proteinogenic Amino Acids in Natural Product Biosynthesis Reviewed

    Sumire Kurosawa, Hironori Okamura, Ayako Yoshida, Takeo Tomita, Yusuke Sone, Fumihito Hasebe, Tetsuro Shinada, Hirosato Takikawa, Saori Kosono, Makoto Nishiyama

    ACS Chemical Biology   2023.01( ISSN:1554-8929 ( eISSN:1554-8937

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acschembio.2c00823

  • Ligand‐Dependant Selective Synthesis of Mono‐ and Dialkenylcarbazoles through Rhodium(III)‐Catalyzed C−H Alkenylation Reviewed

    Rikuto Tanaka, Shiho Ochiai, Asumi Sakai, Yoshinosuke Usuki, Bubwoong Kang, Tetsuro Shinada, Tetsuya Satoh

    Chemistry – An Asian Journal   18 ( 4 )   2023.01( ISSN:1861-4728 ( eISSN:1861-471X

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/asia.202201210

    Other URL: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/asia.202201210

  • A [4Fe-4S] cluster resides at the active center of phosphomevalonate dehydratase, a key enzyme in the archaeal modified mevalonate pathway. Reviewed

    Mutsumi Komeyama, Kohsuke Kanno, Hiroyuki Mino, Yoko Yasuno, Tetsuro Shinada, Tomokazu Ito, Hisashi Hemmi

    Frontiers in microbiology   14   1150353 - 1150353   2023

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    Publishing type:Research paper (scientific journal)   International / domestic magazine:International journal  

    The recent discovery of the archaeal modified mevalonate pathway revealed that the fundamental units for isoprenoid biosynthesis (isopentenyl diphosphate and dimethylallyl diphosphate) are biosynthesized via a specific intermediate, trans-anhydromevalonate phosphate. In this biosynthetic pathway, which is unique to archaea, the formation of trans-anhydromevalonate phosphate from (R)-mevalonate 5-phosphate is catalyzed by a key enzyme, phosphomevalonate dehydratase. This archaea-specific enzyme belongs to the aconitase X family within the aconitase superfamily, along with bacterial homologs involved in hydroxyproline metabolism. Although an iron-sulfur cluster is thought to exist in phosphomevalonate dehydratase and is believed to be responsible for the catalytic mechanism of the enzyme, the structure and role of this cluster have not been well characterized. Here, we reconstructed the iron-sulfur cluster of phosphomevalonate dehydratase from the hyperthermophilic archaeon Aeropyrum pernix to perform biochemical characterization and kinetic analysis of the enzyme. Electron paramagnetic resonance, iron quantification, and mutagenic studies of the enzyme demonstrated that three conserved cysteine residues coordinate a [4Fe-4S] cluster-as is typical in aconitase superfamily hydratases/dehydratases, in contrast to bacterial aconitase X-family enzymes, which have been reported to harbor a [2Fe-2S] cluster.

    DOI: 10.3389/fmicb.2023.1150353

    PubMed

  • Recent Progress in the Synthesis of Deuterated Aldehyde Reviewed

    Tetsuro Shinada, Atsushi Nakayama, Hironori Okamura, Yoko Yasuno

    Bulletin of the Chemical Society of Japan   95 ( 10 )   1461 - 1473   2022.10( ISSN:0009-2673 ( eISSN:1348-0634

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1246/bcsj.20220202

  • Molecular Basis for Enzymatic Aziridine Formation via Sulfate Elimination Reviewed

    Sumire Kurosawa, Fumihito Hasebe, Hironori Okamura, Ayako Yoshida, Kenichi Matsuda, Yusuke Sone, Takeo Tomita, Tetsuro Shinada, Hirosato Takikawa, Tomohisa Kuzuyama, Saori Kosono, Makoto Nishiyama

    Journal of the American Chemical Society   2022.08( ISSN:0002-7863 ( eISSN:1520-5126

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/jacs.2c07243

  • Insight into the mechanism of geranyl-β-phellandrene formation catalyzed by Class IB terpene synthases. Reviewed

    Shogo Iwakata, Kazuya Asada, Tomoyuki Nishi, Rafaella Stepanova, So Shinoda, Daijiro Ueda, Masahiro Fujihashi, Yoko Yasuno, Tetsuro Shinada, Tsutomu Sato

    Bioscience, biotechnology, and biochemistry   86 ( 6 )   724 - 729   2022.05

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    Publishing type:Research paper (scientific journal)   International / domestic magazine:International journal  

    Terpene synthase (TS) from Bacillus alcalophilus (BalTS) is the only Class IB TS for which a 3D structure has been elucidated. Recently, geranyl-β-phellandrene, a novel cyclic diterpene, was identified as a product of BalTS in addition to the acyclic β-springene. In the present study, we have provided insight into the mechanism of geranyl-β-phellandrene formation. Deuterium labeling experiments revealed that the compound is produced via a 1,3-hydride shift. In addition, nonenzymatic reactions using divalent metal ions were performed. The enzyme is essential for the geranyl-β-phellandrene formation. Furthermore, BalTS variants targeting tyrosine residues enhanced the yield of geranyl-β-phellandrene and the proportion of the compound of the total products. It was suggested that the expansion of the active site space may allow the conformation of the intermediates necessary for cyclization. The present study describes the first Class IB TSs to successfully alter product profiles while retaining high enzyme activity.

    DOI: 10.1093/bbb/zbac036

    PubMed

  • Stereoselective Synthesis of Dehydroamino Acids and Its Application to the Synthesis of Nitrogen-containing Natural Products Reviewed

    Yoko Yasuno, Hironori Okamura, Tetsuro Shinada

    Journal of Synthetic Organic Chemistry, Japan   80 ( 4 )   331 - 342   2022.04( ISSN:0037-9980 ( eISSN:1883-6526

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.5059/yukigoseikyokaishi.80.331

  • Structural Basis for the Prenylation Reaction of Carbazole‐Containing Natural Products Catalyzed by Squalene Synthase‐like Enzymes Reviewed

    Ryuhei Nagata, Hironori Suemune, Masaya Kobayashi, Tetsuro Shinada, Kazuo Shin-ya, Makoto Nishiyama, Tomoya Hino, Yusuke Sato, Tomohisa Kuzuyama, Shingo Nagano

    Angewandte Chemie International Edition   2022.03( ISSN:1433-7851 ( eISSN:1521-3773

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/anie.202117430

  • Stereoselective Syntheses of <i>trans</i>-Anhydromevalonic Acid and <i>trans</i>-Anhydromevalonyl Group-Containing Natural Products Reviewed

    Atsushi Nakayama, Yoko Yasuno, Yuki Yamamoto, Kai Saito, Kohei Kitsuwa, Hironori Okamura, Tetsuro Shinada

    Journal of Natural Products   2022.02( ISSN:0163-3864 ( eISSN:1520-6025

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.jnatprod.1c01176

  • Formylation Reaction of Amines Using N-Formylcarbazole. Reviewed

    Bubwoong Kang, Yuki Shimizu, Yusaku Tamura, Eigo Fukuda, Ken-Ichiro Hamamoto, Yuichiro Uchida, Yoko Yasuno, Atsushi Nakayama, Tetsuya Satoh, Masaki Kuse, Tetsuro Shinada

    Chemical & pharmaceutical bulletin   70 ( 7 )   492 - 497   2022

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    Publishing type:Research paper (scientific journal)   International / domestic magazine:Domestic journal  

    Formamides are useful starting materials for pharmaceutical syntheses. Although various synthetic methods have been documented in this regard, the use of N-formylcarbazole as a formylation reagent for amines has not yet been reported. We report here the first examples of the use of N-formylcarbazole for the formylation of amines. The characteristic reactivity of N-formylcarbazole enables the selective formylation of sterically less hindered aliphatic primary and secondary amines. In contrast, sterically bulkier amines and weakly nucleophilic amines such as anilines are less reactive under the reaction conditions.

    DOI: 10.1248/cpb.c22-00161

    PubMed

  • Total Synthesis and Structure Confirmation of trans-Anhydromevalonate-5-phosphate, a Key Biosynthetic Intermediate of the Archaeal Mevalonate Pathway Reviewed

    Yoko Yasuno, Atsushi Nakayama, Kai Saito, Kohei Kitsuwa, Hironori Okamura, Mutsumi Komeyama, Hisashi Hemmi, Tetsuro Shinada

    Journal of Natural Products   84 ( 10 )   2749 - 2754   2021.10( ISSN:0163-3864 ( eISSN:1520-6025

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    Publishing type:Research paper (scientific journal)  

    The mevalonate pathway is an upstream terpenoid biosynthetic route of terpenoids for providing the two five-carbon units, dimethylallyl diphosphate, and isopentenyl diphosphate. Recently, trans-anhydromevalonate-5-phosphate (tAHMP) was isolated as a new biosynthetic intermediate of the archaeal mevalonate pathway. In this study, we would like to report the first synthesis of tAHMP and its enzymatic transformation using one of the key enzymes, mevalonate-5-phosphate dehydratase from a hyperthermophilic archaeon, Aeropyrum pernix. Starting from methyl tetrolate, a Cu-catalyzed allylation provided an E-trisubstituted olefin in a stereoselective manner. The resulting E-olefin was transformed to tAHMP by cleavage of the olefin and phosphorylation. The structure of the synthetic tAHMP was unambiguously determined by NOESY analysis.

    DOI: 10.1021/acs.jnatprod.1c00615

  • Reconstitution of a Highly Reducing Type II PKS System Reveals 6π-Electrocyclization Is Required for <i>o</i>-Dialkylbenzene Biosynthesis. Reviewed

    Zhang J, Yuzawa S, Thong WL, Shinada T, Nishiyama M, Kuzuyama T

    Journal of the American Chemical Society   143 ( 7 )   2962 - 2969   2021.02( ISSN:0002-7863

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/jacs.0c13378

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  • Stereoselective Synthesis of (2S,6R)-Diamino-(5R,7)-dihydroxy-heptanoic Acid (DADH): An Unusual Amino Acid from Streptomyces sp. SANK 60404 Reviewed

    Okamura Hironori, Yasuno Yoko, Nakayama Atsushi, Takikawa Hirosato, Shinada Tetsuro

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   2021.02( ISSN:1434-193X

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/ejoc.202001646

  • Juvenile hormone III skipped bisepoxide is widespread in true bugs (Hemiptera: Heteroptera) Reviewed

    Keiji Matsumoto, Toyomi Kotaki, Hideharu Numata, Tetsuro Shinada, Shin G. Goto

    Royal Society Open Science   8 ( 2 )   2021.02( eISSN:2054-5703

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    Publishing type:Research paper (scientific journal)  

    Juvenile hormone (JH) plays important roles in almost every aspect of insect development and reproduction. JHs are a group of acyclic sesquiterpenoids, and their farnesol backbone has been chemically modified to generate a homologous series of hormones in some insect lineages. JH III (methyl farnesoate, 10,11-epoxide) is the most common JH in insects, but Lepidoptera (butterflies and moths) and 'higher' Diptera (suborder: Brachycera; flies) have developed their own unique JHs. Although JH was first proposed in the hemipteran suborder Heteroptera (true bugs), the chemical identity of the heteropteran JH was only recently determined. Furthermore, recent studies revealed the presence of a novel JH, JH III skipped bisepoxide (JHSB 3), in some heteropterans, but its taxonomic distribution remains largely unknown. In the present study, we investigated JHSB 3 production in 31 heteropteran species, covering almost all heteropteran lineages, through ultra-performance liquid chromatography coupled with tandem mass spectrometry. We found that all of the focal species produced JHSB 3, indicating that JHSB 3 is widespread in heteropteran bugs and the evolutionary occurrence of JHSB 3 ascends to the common ancestor of Heteroptera.

    DOI: 10.1098/rsos.202242

  • Ovicidal activity of juvenile hormone mimics in the bean bug, <i>Riptortus pedestris</i> Reviewed

    Naruse Shouya, Ogino Mayuko, Nakagawa Takao, Yasuno Yoko, Jouraku Akiya, Shiotsuki Takahiro, Shinada Tetsuro, Miura Ken, Minakuchi Chieka

    日本農薬学会 日本農薬学会誌(Journal of Pesticide Science)   2021( ISSN:1348-589X

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    Publishing type:Research paper (scientific journal)  

    <p>Insect juvenile hormone (JH) mimics (JHMs) are known to have ovicidal effects if applied to adult females or eggs. Here, we examined the effects of exogenous JHMs on embryonic development of the bean bug, <i>Riptortus pedestris</i>. The expression profiles of JH early response genes and JH biosynthetic enzymes indicated that JH titer was low for the first 3 days of the egg stage and increased thereafter. Application of JH III skipped bisepoxide (JHSB<sub>3</sub>) or JHM on Day 0 eggs when JH titer was low caused reduced hatchability, and the embryos mainly arrested in mid- or late embryonic stage. Application of JHMs on Day 5 eggs also resulted in an arrest, but this was less effective compared with Day 0 treatment. Interestingly, ovicidal activity of synthetic JHMs was much lower than that of JHSB<sub>3</sub>. This study will contribute to developing novel insecticides that are selective among insect species.</p>

    DOI: 10.1584/jpestics.D20-075

    CiNii Article

  • A novel cyclic peptide (Naturido) modulates glia-neuron interactions in vitro and reverses ageing-related deficits in senescence-accelerated mice. Reviewed

    Ishiguro S, Shinada T, Wu Z, Karimazawa M, Uchidate M, Nishimura E, Yasuno Y, Ebata M, Sillapakong P, Ishiguro H, Ebata N, Ni J, Jiang M, Goryo M, Otsu K, Harada H, Suzuki K

    PloS one   16 ( 1 )   e0245235   2021

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1371/journal.pone.0245235

    PubMed

  • Selective oxidation of alcohol-d1 to aldehyde-d1 using MnO2 Reviewed

    Hironori Okamura, Yoko Yasuno, Atsushi Nakayama, Katsushi Kumadaki, Kohei Kitsuwa, Keita Ozawa, Yusaku Tamura, Yuki Yamamoto, Tetsuro Shinada

    RSC Advances   11 ( 46 )   28530 - 28534   2021( eISSN:2046-2069

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    Publishing type:Research paper (scientific journal)  

    A facile method for deutrium incorporation into aldehydes by mild reduction of NaBD<sub>4</sub> of aldehydes and MnO<sub>2</sub> oxidation (98% D) is disclosed.

    DOI: 10.1039/d1ra05405h

  • Stereoselective Synthesis of (2S,3R)- and (2S,3S)- 2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic Acid Reviewed

    Tetsuro Shinada, Yoko Yasuno, Shunsuke Yamaguchi, Yuma Karita, Kenta Sakai, Hironori Okamura, Atsushi Nakayama

    HETEROCYCLES   103 ( 2 )   965 - 965   2021( ISSN:0385-5414 ( eISSN:1881-0942

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    Publishing type:Research paper (scientific journal)  

    (2S, 3R)-and (2S,3S)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acids (ADHP) are often found in an unusual amino acid component of phomopsin B, ustiloxins, RA-IV, and MPC1001B. Herein, we would like to report stereoselective synthesis of (2S,3R)- and (2S,3S)-ADHP equivalents for the synthesis of ADHP containing natural products. The synthesis is characterized by the stereocontrolled construction of the (2S,3R)-and (2S,3S)-stereocenters starting from Garner's aldehyde as a common starting material.

    DOI: 10.3987/com-20-s(k)70

  • Synthesis of Indenones through Rhodium(III)-Catalyzed [3+2] Annulation Utilizing Recyclable Carbazolyl Leaving Group Reviewed

    Shiho Ochiai, Asumi Sakai, Yoshinosuke Usuki, Bubwoong Kang, Tetsuro Shinada, Tetsuya Satoh

    Chemistry Letters   2020.12( ISSN:0366-7022 ( eISSN:1348-0715

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    DOI: 10.1246/cl.200884

  • Diverse Aromatic Metabolites in the Solitary Tunicate Cnemidocarpa irene Reviewed

    Miyako Kei, Yasuno Yoko, Shinada Tetsuro, Fujita Masaki J., Sakai Ryuichi

    JOURNAL OF NATURAL PRODUCTS   83 ( 10 )   3156 - 3165   2020.10( ISSN:0163-3864

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    © 2020 American Chemical Society. All rights reserved. Fourteen aromatic metabolites (6-19) were isolated from an aqueous extract of the solitary tunicate Cnemidocarpa irene collected in Hokkaido, Japan. The structures of the metabolites were determined based on the spectroscopic interpretations, including one- and two-dimensional NMR, mass spectra, UV, and circular dichroism data. The biopterin analogue 10 modulated the behavior of mice after intracerebroventricular injection and showed a weak affinity to ionotropic glutamate receptor subtypes. Analyses of fluorescent coelomic fluid of the tunicate revealed that pterin 12 was responsible for the fluorescence of the blood cells, while β-carbolines 1 and 3 were fluorescent compounds in the serum. The metabolic profiles in adults, juveniles, larvae, and eggs of the animal differed substantially, suggesting that the metabolism of the animal, especially biosynthesis of aromatic secondary metabolites, changes over different life stages.

    DOI: 10.1021/acs.jnatprod.0c00789

    PubMed

  • Synthesis of Allene-Containing Apocarotenoids by Cross-Coupling Strategy Reviewed

    Sakaguchi Kazuhiko, Nishioka Yuto, Kinashi Naoto, Yukihira Nao, Shinada Tetsuro, Nishimura Takahiro, Hashimoto Hideki, Katsumura Shigeo

    SYNTHESIS-STUTTGART   52 ( 20 )   3007 - 3017   2020.10( ISSN:0039-7881

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    © 2020 Georg Thieme Verlag. All rights reserved. The stereocontrolled total synthesis of the allene and carbonyl conjugated apocarotenoids, paracentrone and 19-hexanoyloxyparacentrone 3-acetate, was achieved by sequential cross-coupling reactions using boronic acid ester and iodine- or tin-substituted C5 dienes, which were the building blocks for the elongation of the conjugated polyene systems at both terminals.

    DOI: 10.1055/s-0040-1707906

  • Biosynthetic reaction mechanism of terpene synthases by using deuterium labelled acyclic terpenes Reviewed

    Tetsuro Shinada

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   78 ( 10 )   952 - 961   2020.10( ISSN:0037-9980

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    © 2020 Society of Synthetic Organic Chemistry. All rights reserved. Terpenoids including more than 80,000 species are ubiquitous in nature. The biosynthetic reaction mechanism to produce diverse range of terpene skeleton from simple biosynthetic precursors, dimethylallylpyrophosphate (3) and isopentenylpyrophosphate (4) has attracted much attention. In this article, biosynthetic reaction mechanisms of terpene synthases by using deuterium labelled acyclic terpene probes are described. Five different kinds of deuterium labeled geranylgeranyl pyrophosphates are selectively synthesized by Z - selective formation of a vinyl tosylate followed by the Negishi coupling reaction as well as Pd catalyzed reductive desulfonylation reaction. The deuterium - labelled geranylgeranyl pyrophosphates are treated with a diterpene cyclase, CotB2to provide the cyclization products. Structure analysis of the cyclization products was performed by nuclear magnetic resonance spectroscopy to trace the deuterium in the products. Based on the analysis, a unique biosynthetic reaction mechanism of CotB2via cyclopro- pylcarbinyl cation rearrangement with the methylene chain exchanging at C8 and C9 was proposed. The stereoselectivity of the characteristic cyclopropane rearrangement was discussed from the comparative viewpoints of the previous studies on the acid catalyzed transformation of thujopsenes, biosynthetic studies of verrucosane-2β-ol, and tsukubadiene in which the cyclo- propane rearrangement mechanism is involved in the transformation.

    DOI: 10.5059/yukigoseikyokaishi.78.952

  • Molecular Basis for Sesterterpene Diversity Produced by Plant Terpene Synthases Reviewed

    Qingwen Chen, Jianxu Li, Zhixi Liu, Takaaki Mitsuhashi, Yuting Zhang, Haili Liu, Yihua Ma, Juan He, Tetsuro Shinada, Tsutomu Sato, Yong Wang, Hongwei Liu, Ikuro Abe, Peng Zhang, Guodong Wang

    Plant Communications   1 ( 5 )   100051   2020.09

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    © 2020 The Author(s) Class I terpene synthase (TPS) generates bioactive terpenoids with diverse backbones. Sesterterpene synthase (sester-TPS, C25), a branch of class I TPSs, was recently identified in Brassicaceae. However, the catalytic mechanisms of sester-TPSs are not fully understood. Here, we first identified three nonclustered functional sester-TPSs (AtTPS06, AtTPS22, and AtTPS29) in Arabidopsis thaliana. AtTPS06 utilizes a type-B cyclization mechanism, whereas most other sester-TPSs produce various sesterterpene backbones via a type-A cyclization mechanism. We then determined the crystal structure of the AtTPS18–FSPP complex to explore the cyclization mechanism of plant sester-TPSs. We used structural comparisons and site-directed mutagenesis to further elucidate the mechanism: (1) mainly due to the outward shift of helix G, plant sester-TPSs have a larger catalytic pocket than do mono-, sesqui-, and di-TPSs to accommodate GFPP; (2) type-A sester-TPSs have more aromatic residues (five or six) in their catalytic pocket than classic TPSs (two or three), which also determines whether the type-A or type-B cyclization mechanism is active; and (3) the other residues responsible for product fidelity are determined by interconversion of AtTPS18 and its close homologs. Altogether, this study improves our understanding of the catalytic mechanism of plant sester-TPS, which ultimately enables the rational engineering of sesterterpenoids for future applications.

    DOI: 10.1016/j.xplc.2020.100051

    PubMed

  • N-Acylcarbazole as a Selective Transamidation Reagent Reviewed

    Kang Bubwoong, Yasuno Yoko, Okamura Hironori, Sakai Asumi, Satoh Tetsuya, Kuse Masaki, Shinada Tetsuro

    公益社団法人 日本化学会 BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   93 ( 8 )   993 - 999   2020.08( ISSN:0009-2673

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    <p><i>N</i>-acylation reaction offers an opportunity to develop an efficient synthesis of amide group-containing molecules. We found that <i>N</i>-acyl carbazoles showed remarkable selectivity in transamidation. Sterically less hindered primary amines are selectively acylated with <i>N</i>-acyl carbazoles without any additives. Various functional groups such as alcohol, phenol, indole, and aniline moieties are tolerated under mild conditions. The synthetic utility was displayed in one-pot synthesis of an <i>N</i>-acyl polyamine natural product. The terminal amines of spermidine were selectively benzoylated with <i>N</i>-benzoyl carbazole, followed by acetylation reaction accomplished the total synthesis in a highly efficient manner.</p>

    DOI: 10.1246/bcsj.20200116

    CiNii Article

  • Characterization of Class IB Terpene Synthase: The First Crystal Structure Bound with a Substrate Surrogate Reviewed

    Stepanova Rafaella, Inagi Hayato, Sugawara Kei, Asada Kazuya, Nishi Tomoyuki, Ueda Daijiro, Yasuno Yoko, Shinada Tetsuro, Miki Kunio, Fujihashi Masahiro, Sato Tsutomu

    ACS CHEMICAL BIOLOGY   15 ( 6 )   1517 - 1525   2020.06( ISSN:1554-8929

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    Terpene synthases (TS) are classified into two broad types, Class I and II, based on the chemical strategy for initial carbocation formation and motif sequences of the catalytic site. We have recently identified a new class of enzymes, Class IB, showing the acceptability of long (C20-C35) prenyl-diphosphates as substrates and no amino acid sequence homology with known TS. Conversion of long prenyl-diphosphates such as heptaprenyl-diphosphate (C35) is unusual and has never been reported for Class I and II enzymes. Therefore, the characterization of Class IB enzymes is crucial to understand the reaction mechanism of the extensive terpene synthesis. Here, we report the crystal structure bound with a substrate surrogate and biochemical analysis of a Class IB TS, using the enzyme from Bacillus alcalophilus (BalTS). The structure analysis revealed that the diphosphate part of the substrate is located around the two characteristic Asp-rich motifs, and the hydrophobic tail is accommodated in a unique hydrophobic long tunnel, where the C35 prenyl-diphosphate, the longest substrate of BalTS, can be accepted. Biochemical analyses of BalTS showed that the enzymatic property, such as Mg2+ dependency, is similar to those of Class I enzymes. In addition, a new cyclic terpene was identified from BalTS reaction products. Mutational analysis revealed that five of the six Asp residues in the Asp-rich motifs and two His residues are essential for the formation of the cyclic skeleton. These results provided a clue to consider the application of the unusual large terpene synthesis by Class IB enzymes.

    DOI: 10.1021/acschembio.0c00145

    PubMed

  • Structure Determination of Juvenile Hormone from Chagas Disease Vectors, Rhodnius prolixus and Triatoma infestans Reviewed

    Matsumoto Keiji, Yasuno Yoko, Yasuda Kohei, Hayashi Tsuyoshi, Goto Shin G., Shinada Tetsuro

    公益社団法人 日本化学会 CHEMISTRY LETTERS   49 ( 5 )   538 - 541   2020.05( ISSN:0366-7022

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    <p>The juvenile hormone (JH) is a key hormone of insects. In this study, the first structure determination of JH of <i>Rhodnius prolixus</i> (Heteroptera; Reduviidae) known historically as the insect for which the juvenile hormone was discovered, is reported. This species is also known as a medically important pest associated with Chagas disease. The relative and absolute stereochemistry was unambiguously determined to be methyl (2<i>R</i>,3<i>S</i>)-3-((<i>E</i>)-6-((<i>R</i>)-3,3-dimethyloxiran-2-yl)-4-methylhex-3-en-1-yl)-3-methyloxirane-2-carboxylate (JHSB<sub>3</sub>) by highly sensitive UPLC MS/MS method.</p>

    DOI: 10.1246/cl.200126

    CiNii Article

  • A stereoisomer of JHSB(3) with 10S-configuration, 10S-JHSB(3), biosynthesized by the corpus allatum of the brown marmorated stink bug, Halyomorpha halys (Hemiptera: Pentatomidae) Reviewed

    Kotaki Toyomi, Matsumoto Keiji, Kaihara Kanako, Ando Yumi, Misaki Kumi, Shinada Tetsuro

    APPLIED ENTOMOLOGY AND ZOOLOGY   55 ( 2 )   223 - 229   2020.05( ISSN:0003-6862

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    © 2020, The Japanese Society of Applied Entomology and Zoology. The products released by the corpus allatum (CA), an endocrine gland producing juvenile hormone (JH), were analyzed in three species of stink bugs. Liquid chromatography–mass spectrometry (LC–MS) analysis of the CA products from female adults of Halyomorpha halys (Stål), Nezara viridula (Linnaeus), and Nezara antennata Scott (Hemiptera: Pentatomidae) revealed that the CA biosynthesized JH III skipped bisepoxyside (JHSB3) in all three species. In H. halys, in addition to JHSB3, the CA also produced its stereoisomer, 10S-JHSB3. A bioassay focusing on the number of antennal segments was adopted to examine biological activity of these products. When last instar nymphs were treated with either of the two JHs, they emerged as adults bearing nymphal type antennae with four segments in a dose-dependent fashion, indicating that both JHSB3 and 10S-JHSB3 had the JH activity in H. halys. Therefore, for the first time, 10S-JHSB3 in H. halys was found to be a naturally occurring JH molecule with 10S-configuration.

    DOI: 10.1007/s13355-020-00674-x

  • γ-C (sp<sup>3</sup>)-H bond functionalisation of α,β-unsaturated amides through an umpolung strategy. Reviewed

    Futaki E, Takeda N, Yasui M, Shinada T, Miyata O, Ueda M

    Organic & biomolecular chemistry   2020.02( ISSN:1477-0520

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    DOI: 10.1039/d0ob00125b

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  • Juvenile hormone III skipped bisepoxide, not its stereoisomers, as a juvenile hormone of the bean bug Riptortus pedestris. Reviewed

    Ando Y, Matsumoto K, Misaki K, Mano G, Shiga S, Numata H, Kotaki T, Shinada T, Goto SG

    General and comparative endocrinology   289   113394   2020.01( ISSN:0016-6480

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    DOI: 10.1016/j.ygcen.2020.113394

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  • SYNTHESIS OF OPTICALLY ACTIVE (R)- AND (S)-beta-ARGININE FROM PYROGLUTAMIC ACID Reviewed

    Yasuno Yoko, Sawai Akira, Sekihara Ai, Shinada Tetsuro

    HETEROCYCLES   101 ( 1 )   165 - 176   2020.01( ISSN:0385-5414

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    © 2020 The Japan Institute of Heterocyclic Chemistry – The first synthesis of optically active β-arginine was achieved starting from commercially available pyroglutamic acid. The new synthetic protocol is characterized by the use of nitrile as a carboxylic acid surrogate which could be transformed to the corresponding 2-acyl-1,3-bis(1,1-dimethylethyl)imidodi-carbonic acid ester (active amide) via Pt-catalyzed hydration under the mild conditions. The active amide was converted to β-arginine and Boc-β-Arg-Val-OMe in good yield.

    DOI: 10.3987/COM-19-S(F)6

  • Reagent-controlled regiodivergence in the [3,3]-sigmatropic rearrangement of N-(acyloxy) enamides Reviewed

    Takeda Norihiko, Arisawa Narumi, Miyamoto Misaki, Kobori Yukiko, Shinada Tetsuro, Miyata Okiko, Ueda Masafumi

    ORGANIC CHEMISTRY FRONTIERS   6 ( 22 )   3721 - 3724   2019.11( ISSN:2052-4129

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    DOI: 10.1039/c9qo01109a

  • Burkholderia gut symbiont modulates titer of specific juvenile hormone in the bean bug Riptortus pedestris Reviewed

    Lee Junbeom, Kim Chan-Hee, Jang Ho Am, Kim Jiyeun Kate, Kotaki Toyomi, Shinoda Tetsuro, Shinada Tetsuro, Yoo Jin-Wook, Lee Bok Luel

    DEVELOPMENTAL AND COMPARATIVE IMMUNOLOGY   99   103399   2019.10( ISSN:0145-305X

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    DOI: 10.1016/j.dci.2019.103399

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  • Acid-catalyzed chirality-transferring intramolecular Friedel-Crafts cyclization of alpha-hydroxy-alpha-alkenylsilanes Reviewed

    Sakaguchi Kazuhiko, Kubota Shunnichi, Akagi Wataru, Ikeda Naoko, Higashino Masato, Ariyoshi Shoma, Shinada Tetsuro, Ohfune Yasufumi, Nishimura Takahiro

    CHEMICAL COMMUNICATIONS   55 ( 59 )   8635 - 8638   2019.07( ISSN:1359-7345

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    DOI: 10.1039/c9cc03509e

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  • First synthesis of all-trans-polyprenol with 100 carbons Reviewed

    Yusuke Totsuka, Yoko Yasuno, Tetsuro Shinada

    Chemistry Letters   48 ( 5 )   491 - 494   2019.05( ISSN:0366-7022

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    © 2019 The Chemical Society of Japan. All-trans polyprenols consisting of one hundred carbons (C100) have been synthesized for the first time via the sulfone coupling of C45 and C55 fragments. The resulting coupling product with four benzenesulfonyl groups were subjected to desulfonylation reaction using Pd(dppp)Cl2/LiBHEt3 followed by removal of the benzyl group at the tail under Benkeser reduction conditions to furnish the title compound.

    DOI: 10.1246/cl.190046

    CiNii Article

  • Catalytic Asymmetric Hydrogenation of Dehydroamino Acid Ester with Biscarbamate Protection and Its Application to Synthesis of xCT inhibitor. Reviewed

    Yasuno Y, Mizutani I, Sueuchi Y, Wakabayashi Y, Yasuo N, Shimamoto K, Shinada T

    Chemistry (Weinheim an der Bergstrasse, Germany)   2019.02( ISSN:0947-6539

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/chem.201900289

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  • Chiral isoxazolidine-mediated stereoselective umpolung alpha-phenylation of methyl ketones Reviewed

    Takeda Norihiko, Furuishi Mizuki, Nishijima Yuri, Futaki Erika, Ueda Masafumi, Shinada Tetsuro, Miyata Okiko

    ORGANIC & BIOMOLECULAR CHEMISTRY   16 ( 46 )   8940 - 8943   2018.12( ISSN:1477-0520

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/c8ob02480d

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  • An aromatic farnesyltransferase functions in biosynthesis of the anti-HIV meroterpenoid daurichromenic acid. Reviewed

    Saeki H, Hara R, Takahashi H, Iijima M, Munakata R, Kenmoku H, Fuku K, Sekihara A, Yasuno Y, Shinada T, Ueda D, Nishi T, Sato T, Asakawa Y, Kurosaki F, Yazaki K, Taura F

    Plant physiology   178 ( 2 )   535 - 551   2018.10( ISSN:0032-0889

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    DOI: 10.1104/pp.18.00655

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  • Improved total synthesis of (+/-)-Tetragocarbone A Reviewed

    Nishimura Eiji, Yasuno Yoko, Shinada Tetsuro

    TETRAHEDRON   74 ( 21 )   2664 - 2668   2018.05( ISSN:0040-4020

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tet.2018.04.024

  • Crystal structure and functional analysis of large-terpene synthases belonging to a newly found subclass Reviewed

    Fujihashi Masahiro, Sato Tsutomu, Tanaka Yuma, Yamamoto Daisuke, Nishi Tomoyuki, Ueda Daijiro, Murakami Mizuki, Yasuno Yoko, Sekihara Ai, Fuku Kazuma, Shinada Tetsuro, Miki Kunio

    CHEMICAL SCIENCE   9 ( 15 )   3754 - 3758   2018.04( ISSN:2041-6520

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/c8sc00289d

  • Stereocontrolled Synthesis of 19 '-Deoxyperidinin Reviewed

    Kinashi Naoto, Katsumura Shigeo, Shinada Tetsuro, Sakaguchi Kazuhiko

    ORGANIC LETTERS   20 ( 3 )   582 - 585   2018.02( ISSN:1523-7060

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    DOI: 10.1021/acs.orglett.7b03695

  • Structure and Mechanism of the Monoterpene Cyclolavandulyl Diphosphate Synthase that Catalyzes Consecutive Condensation and Cyclization Reviewed

    Tomita Takeo, Kobayashi Masaya, Karita Yuma, Yasuno Yoko, Shinada Tetsuro, Nishiyama Makoto, Kuzuyama Tomohisa

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   56 ( 47 )   14913 - 14917   2017.11( ISSN:1433-7851

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/anie.201708474

  • Isolation of biologically active peptides from the venom of Japanese carpenter bee, Xylocopa appendiculata Reviewed

    Kawakami Hiroko, Goto Shin G., Murata Kazuya, Matsuda Hideaki, Shigeri Yasushi, Imura Tomohiro, Inagaki Hidetoshi, Shinada Tetsuro

    JOURNAL OF VENOMOUS ANIMALS AND TOXINS INCLUDING TROPICAL DISEASES   23 ( 1 )   2017.05( ISSN:1678-9199

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1186/s40409-017-0119-6

  • Upregulation of Juvenile Hormone Titers in Female Drosophila melanogaster Through Mating Experiences and Host Food Occupied by Eggs and Larvae Reviewed

    Sugime Yasuhiro, Watanabe Dai, Yasuno Yoko, Shinada Tetsuro, Miura Toru, Tanaka Nobuaki K.

    ZOOLOGICAL SCIENCE   34 ( 1 )   52 - 57   2017.02( ISSN:0289-0003

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    DOI: 10.2108/zs160150

  • Stereocontrolled Synthesis of Paracentrone Reviewed

    Nishioka Yuto, Yano You, Kinashi Naoto, Oku Natsumi, Toriyama Yohei, Katsumura Shigeo, Shinada Tetsuro, Sakaguchi Kazuhiko

    SYNLETT   28 ( 3 )   327 - 332   2017.02( ISSN:0936-5214

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/s-0036-1588906

  • カメムシから見つかった新規幼若ホルモンの構造決定:構造推理を出発点とする超微量天然物の構造決定 Reviewed

    品田 哲郎, 保野 陽子, 小滝 豊美

    公益社団法人 日本農芸化学会 化学と生物   56 ( 1 )   10 - 12   2017( ISSN:0453-073X

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    DOI: 10.1271/kagakutoseibutsu.56.10

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  • Structure-activity relationship study at C9 position of kaitocephalin Reviewed

    Yasuno Yoko, Hamada Makoto, Yoshida Yuya, Shimamoto Keiko, Shigeri Yasushi, Akizawa Toshifumi, Konishi Motomi, Ohfune Yasufumi, Shinada Tetsuro

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   26 ( 15 )   3543 - 3546   2016.08( ISSN:0960-894X

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    DOI: 10.1016/j.bmcl.2016.06.026

  • Structure Determination of Monomeric Phloroglucinol Derivatives with a Cinnamoyl Group Isolated from Propolis of the Stingless Bee, Tetragonula carbonaria Reviewed

    Nishimura Eiji, Murakami Shino, Suzuki Koichi, Amano Kazuhiro, Tanaka Rika, Shinada Tetsuro

    ASIAN JOURNAL OF ORGANIC CHEMISTRY   5 ( 7 )   855 - 859   2016.07( ISSN:2193-5807

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/ajoc.201600106

  • Oosorption in the stink bug Plautia stali: role of Juvenile hormone in the induction of oosorption Reviewed

    Kotaki Toyomi, Kaihara Kanako, Ando Yumi, Misaki Kumi, Shinada Tetsuro

    PHYSIOLOGICAL ENTOMOLOGY   41 ( 2 )   127 - 131   2016.06( ISSN:0307-6962

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1111/phen.12136

  • Chemistry of New Insect Juvenile Hormone: Structure Determination, Structure-activity Relationship Study, and Synthesis Reviewed

    Shinada Tetsuro

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   74 ( 6 )   611 - 620   2016.06( ISSN:0037-9980

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    Publishing type:Research paper (scientific journal)   Kind of work:Single Work  

  • Effect of Asiasarum Root Extract and Its Constituents on Interleukin-1 beta-Stimulated Matrix Metalloproteinase-1 Secretion from Human Gingival Fibroblasts Reviewed

    Futamura-Masuda Megumi, Yokota-Honda Mami, Anraku Takuya, Nakanishi Kanae, Murata Kazuya, Shinada Tetsuro, Matsuda Hideaki

    BIOLOGICAL & PHARMACEUTICAL BULLETIN   39 ( 5 )   823 - 831   2016.05( ISSN:0918-6158

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  • ヒト歯肉線維芽細胞からのインターロイキン1β刺激性マトリックスメタロプロテイナーゼ-1の分泌に対する細辛抽出物とその成分の効果(Effect of Asiasarum Root Extract and Its Constituents on Interleukin-1β-Stimulated Matrix Metalloproteinase-1 Secretion from Human Gingival Fibroblasts) Reviewed

    Futamura-Masuda Megumi, Yokota-Honda Mami, Anraku Takuya, Nakanishi Kanae, Murata Kazuya, Shinada Tetsuro, Matsuda Hideaki

    (公社)日本薬学会 Biological & Pharmaceutical Bulletin   39 ( 5 )   823 - 831   2016.05( ISSN:0918-6158

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    口臭症や歯周病に対する細辛とその成分の効果を検討した。細辛の50%エタノール抽出物(AR-ext)は、200μg/mLでL-メチオニンγ-リアーゼ阻害活性を示し、10および50μg/mLでヒト歯肉線維芽細胞(HGF)からのインターロイキン(IL)-1β刺激性マトリックスメタロプロテイナーゼ(MMP)-1の分泌を阻害した。MMP-1分泌阻害の活性成分として2つの不飽和脂肪酸アミドを単離した。MMP-1分泌の阻害機構を解明するために、マイトジェン活性化プロテインキナーゼ(MAPK)のリン酸化に対する(2E,4E,8Z,10Z)-N-(2-methylpropyl)dodeca-2,4,8,10-tetraenamide(2)の効果を検討した。ウェスタンブロット分析では、2(10μM)はP38およびc-Jun-N末端キナーゼのリン酸化を減少させた。以上より、2はMAPKリン酸化の下方制御により細胞内MMP-1の発現とIL-1β刺激HGFからのMMP-1分泌を抑制することが示唆された。

  • Spectroscopic Investigation of the Carotenoid Deoxyperidinin: Direct Observation of the Forbidden S-0 -> S-1 Transition Reviewed

    Greco Jordan A., LaFountain Amy M., Kinashi Naoto, Shinada Tetsuro, Sakaguchi Kazuhiko, Katsumura Shigeo, Magdaong Nikki Cecil M., Niedzwiedzki Dariusz M., Birge Robert R., Frank Harry A.

    JOURNAL OF PHYSICAL CHEMISTRY B   120 ( 10 )   2731 - 2744   2016.03( ISSN:1520-6106

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.jpcb.6b00439

  • Preparation of E-alpha-stannyl-beta-trimethylsilylethynylacrylate, building block for polyconjugated ylidenebutenolide and its derivatives, by novel E-selective ethynylstannylation of propiolate Reviewed

    Kinashi Naoto, Sakaguchi Kazuhiko, Katsumura Shigeo, Shinada Tetsuro

    TETRAHEDRON LETTERS   57 ( 1 )   129 - 132   2016.01( ISSN:0040-4039

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tetlet.2015.11.079

  • Effect of Asiasarum Root Extract and Its Constituents on Interleukin-1β-Stimulated Matrix Metalloproteinase-1 Secretion from Human Gingival Fibroblasts Reviewed

    Futamura-Masuda Megumi, Yokota-Honda Mami, Anraku Takuya, Nakanishi Kanae, Murata Kazuya, Shinada Tetsuro, Matsuda Hideaki

    公益社団法人 日本薬学会 Biological & Pharmaceutical Bulletin   39 ( 5 )   823 - 831   2016( ISSN:0918-6158

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    Asiasarum root (roots and rhizome of <i>Asiasarum sieboldii</i> or <i>A. heterotropoides</i> var. <i>mandshuricum</i>) has been frequently used in traditional Chinese medicinal formulas for the management of oral malodor syndrome caused by periodontal disease. However, there are no scientific reports concerning these effects and the mechanism of action. The objective of this study was to examine the inhibitory effects of Asiasarum root and its constituents on oral malodor syndrome and periodontal disease. A 50% ethanolic extract of Asiasarum root (AR-ext) showed L-methionine γ-lyase (METase) inhibitory activity at a concentration of 200 µg/mL, and inhibited interleukin (IL)-1β-stimulated matrix metalloproteinase (MMP)-1 secretion from human gingival fibroblasts (HGFs) at a concentration of 10 and 50 µg/mL without cytotoxic effects. Activity-guided fractionation of the AR-ext suggested that METase inhibitory activity was attributable to a mixture of linoleic and oleic acid, because these unsaturated fatty acids showed weak METase inhibitory activities. Similar fractionation using MMP-1 secretion inhibitory activity led to the isolation of two unsaturated fatty acid amides, (2<i>E</i>,4<i>E</i>,8<i>Z</i>,10<i>E</i>)-<i>N</i>-(2-methylpropyl)dodeca-2,4,8,10-tetraenamide (<b>1</b>) and (2<i>E</i>,4<i>E</i>,8<i>Z</i>,10<i>Z</i>)-<i>N</i>-(2-methylpropyl)dodeca-2,4,8,10-tetraenamide (<b>2</b>), as active constituents with inhibitory activity on MMP-1 secretion from HGFs. To elucidate the inhibition mechanism on MMP-1 secretion, the effect of <b>2</b> on mitogen-activated protein kinase (MAPK) phosphorylation was examined. Western blotting analysis revealed that <b>2</b> (10 µM) reduced the phosphorylation of p38 and c-Jun-N-terminal kinase. These results suggested that <b>2</b> suppresses intracellular MMP-1 expression and MMP-1 secretion from IL-1β-stimulated HGFs by down-regulation of MAPK phosphorylation.

    DOI: 10.1248/bpb.b15-01000

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  • (7S)-Kaitocephalin as a potent NMDA receptor selective ligand Reviewed

    Yasuno Yoko, Hamada Makoto, Kawasaki Masanori, Shimamoto Keiko, Shigeri Yasushi, Akizawa Toshifumi, Konishi Motomi, Ohfune Yasufumi, Shinada Tetsuro

    ORGANIC & BIOMOLECULAR CHEMISTRY   14 ( 4 )   1206 - 1210   2016( ISSN:1477-0520

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    DOI: 10.1039/c5ob02301g

  • The stereoselective construction of E- and Z-Delta-Ile from E-dehydroamino acid ester: the synthesis of the phomopsin A tripeptide side chain Reviewed

    Yasuno Yoko, Nishimura Akito, Yasukawa Yoshifumi, Karita Yuma, Ohfune Yasufumi, Shinada Tetsuro

    CHEMICAL COMMUNICATIONS   52 ( 7 )   1478 - 1481   2016( ISSN:1359-7345

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/c5cc08458j

  • Chemistry of New Insect Juvenile Hormone: Structure Determination, Structure-activity Relationship Study, and Synthesis Reviewed

    Shinada Tetsuro

    The Society of Synthetic Organic Chemistry, Japan, Journal of Synthetic Organic Chemistry, Japan   74 ( 6 )   611 - 620   2016( ISSN:0037-9980

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    The first structure determination of the new juvenile hormone (JH) isolated from a heteropteran insect, <i>Plautia stali</i> is described. To identify the target JH, a new isolation approach starting from a JH molecular library was attempted. We proposed the structure of the target JH based on the <i>in vitro</i> radiochemical TLC and mass analyses of the corpus allatum product of <i>P. stali</i>. The molecular library including 32 molecules was prepared from geranylacetone. The mixture was screened by the bioassay-guided separation using <i>P. stali</i>. The highly potent JH molecules found in the library were subjected to GCMS analysis to identify the naturally occurring heteropteran JH obtained from <i>P. stali</i>. One of the candidates was identical with the natural product by a chiral GCMS analysis. The novel JH was named as juvenile hormone III skipped bisepoxide(JHSB<sub>3</sub>). To identify the key functional groups of JHSB<sub>3</sub>, we conducted the structure-activity relationship study of JHSB<sub>3</sub>. These results as well as our efforts for the stereoselective synthesis of JH0 and JHI are also described.

    DOI: 10.5059/yukigoseikyokaishi.74.611

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  • "Cation-Stitching Cascade": exquisite control of terpene cyclization in cyclooctatin biosynthesis Reviewed

    Sato Hajime, Teramoto Kazuya, Masumoto Yui, Tezuka Noriyuki, Sakai Kenta, Ueda Shota, Totsuka Yusuke, Shinada Tetsuro, Nishiyama Makoto, Wang Chao, Kuzuyama Tomohisa, Uchiyama Masanobu

    SCIENTIFIC REPORTS   5   2015.12( ISSN:2045-2322

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    DOI: 10.1038/srep18471

  • A FACILE SYNTHESIS OF (2R/S,5R)-1-tert-BUTYL 2-METHYL 5-(((tert-BUTYLDIMETHYLSILYL)OXY)METHYL)PYRROLIDINE-1,2-DICARBOXYLATE Reviewed

    Yasuno Yoko, Yoshida Yuya, Nishimura Akito, Ohfune Yasufumi, Shinada Tetsuro

    HETEROCYCLES   91 ( 12 )   2377 - 2385   2015.12( ISSN:0385-5414

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    DOI: 10.3987/COM-15-13347

  • Cyclopropanation of (E)-Dehydroaspartic Acid Esters with Furan Derivatives: The Synthesis of Highly Functionalized alpha-2,3-Methanoamino Acid Esters Reviewed

    Manabe Atsushi, Matsumoto Ryotaro, Shinada Tetsuro

    SYNLETT   26 ( 12 )   1710 - 1714   2015.07( ISSN:0936-5214

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/s-0034-1380812

  • Biosynthesis of Sesterterpenes, Head-to-Tail Triterpenes, and Sesquarterpenes in Bacillus clausii: Identification of Multifunctional Enzymes and Analysis of Isoprenoid Metabolites Reviewed

    Ueda Daijiro, Yamaga Hiroaki, Murakami Mizuki, Totsuka Yusuke, Shinada Tetsuro, Sato Tsutomu

    CHEMBIOCHEM   16 ( 9 )   1371 - 1377   2015.06( ISSN:1439-4227

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/cbic.201500138

  • Facile Synthesis of Deuterium-Labelled Geranylgeraniols Reviewed

    Totsuka Yusuke, Ueda Shota, Kuzuyama Tomohisa, Shinada Tetsuro

    公益社団法人 日本化学会 BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   88 ( 4 )   575 - 577   2015.04( ISSN:0009-2673

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    Facile and stereoselective syntheses of three different kinds of deuterium-labelled geranylgeraniol analogs have been achieved. LiAlD<sub>4</sub> is used as the deuterium source to ensure high deuterium incorporation. [8,8-<i>d</i><sub>2</sub>]- and [9,9-<i>d</i><sub>2</sub>]-geranylgeraniols have been prepared for the first time. [10-<i>d</i>]-geranylgeraniol was efficiently prepared with a high degree of deuterium incorporation.

    DOI: 10.1246/bcsj.20140384

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  • Total Synthesis of a Monomeric Phloroglucinol Derivative Isolated from Myrtus communis Reviewed

    Nishimura Eiji, Ohfune Yasufumi, Shinada Tetsuro

    公益社団法人 日本化学会 CHEMISTRY LETTERS   44 ( 4 )   445 - 447   2015.04( ISSN:0366-7022

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    The first total synthesis of a monomeric phloroglucinol [(1<i>R*</i>,2<i>S*</i>)-2-hydroxy-2-isobutyl-4,4,6,6-tetramethyl-3,5-dioxocyclohexyl acetate] was achieved by stereoselective reduction of a symmetrical &alpha;-ketol as a key step. The corresponding <i>cis</i>-stereoisomer of the natural product was synthesized from phloroglucinol via <i>cis</i>-dihydroxylation using OsO<sub>4</sub>. Comparison of <sup>1</sup>H NMR data for synthetic <b>1</b> and <b>2</b> confirmed the <i>trans</i>-stereochemistry of the natural product.

    DOI: 10.1246/cl.141168

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  • An Unusual Terpene Cyclization Mechanism Involving a Carbon-Carbon Bond Rearrangement Reviewed

    Meguro Ayuko, Motoyoshi Yudai, Teramoto Kazuya, Ueda Shota, Totsuka Yusuke, Ando Yumi, Tomita Takeo, Kim Seung-Young, Kimura Tomoyuki, Igarashi Masayuki, Sawa Ryuichi, Shinada Tetsuro, Nishiyama Makoto, Kuzuyama Tomohisa

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   54 ( 14 )   4353 - 4356   2015.03( ISSN:1433-7851

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/anie.201411923

  • Total synthesis and structure elucidation of (+/-)-triumphalone and (+/-)-isotriumphalone Reviewed

    Nishimura Eiji, Ohfune Yasufumi, Shinada Tetsuro

    TETRAHEDRON LETTERS   56 ( 3 )   539 - 541   2015.01( ISSN:0040-4039

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tetlet.2014.12.005

  • Reaction of cyclopropenes with a trichloromethyl radical: unprecedented ring-opening reaction of cyclopropanes with migration Reviewed

    Ueda Masafumi, Doi Nobuyoshi, Miyagawa Hitoki, Sugita Shoichi, Takeda Norihiko, Shinada Tetsuro, Miyata Okiko

    CHEMICAL COMMUNICATIONS   51 ( 20 )   4204 - 4207   2015( ISSN:1359-7345

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/c4cc09649e

  • Acute and Sub-chronic Toxicity Analyses of Hot-Water Extract of Isaria japonica from Silkworm (Bombyx mori) Pupae Reviewed

    Sillapakong Piyamas, Goryo Masanobu, Sasaki Jun, Oda Shinichi, Hiraga Takashi, Uchiyama Shorta, Nishimura Eiji, Shinada Tetsuro, Ohtsuka Chigumi, Terayama Yasuo, Suzuki Koichi

    CURRENT TRADITIONAL MEDICINE   1 ( 3 )   184 - 192   2015( ISSN:2309-608X

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.2174/221508380103151231145946

  • Toward the total synthesis of tetrodotoxin: stereoselective construction of the 7-oxanorbornane intermediate Reviewed

    Manabe Atsushi, Ohfune Yasufumi, Shinada Tetsuro

    TETRAHEDRON LETTERS   55 ( 44 )   6077 - 6080   2014.10( ISSN:0040-4039

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tetlet.2014.09.036

  • Short Total Synthesis of (-)-Kainic Acid Reviewed

    Oe Kentaro, Ohfune Yasufumi, Shinada Tetsuro

    ORGANIC LETTERS   16 ( 9 )   2550 - 2553   2014.05( ISSN:1523-7060

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/ol5009526

  • Cyclolavandulyl Skeleton Biosynthesis via Both Condensation and Cyclization Catalyzed by an Unprecedented Member of the cis-Isoprenyl Diphosphate Synthase Superfamily Reviewed

    Ozaki Taro, Zhao Ping, Shinada Tetsuro, Nishiyama Makoto, Kuzuyama Tomohisa

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   136 ( 13 )   4837 - 4840   2014.04( ISSN:0002-7863

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/ja500270m

  • Solid phase synthesis of alpha-amino squaric acid-containing peptides Reviewed

    Maeda Kentaro, Kiniwa Yu-ichi, Ohfune Yasufumi, Ishiguro Shinichi, Suzuki Koichi, Murata Kazuya, Matsuda Hideaki, Shinada Tetsuro

    RSC ADVANCES   4 ( 92 )   50639 - 50643   2014( ISSN:2046-2069

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/c4ra10442k

  • Identification of Novel Sesterterpene/Triterpene Synthase from Bacillus clausii Reviewed

    Sato Tsutomu, Yamaga Hiroaki, Kashima Shoji, Murata Yusuke, Shinada Tetsuro, Nakano Chiaki, Hoshino Tsutomu

    CHEMBIOCHEM   14 ( 7 )   822 - 825   2013.05( ISSN:1439-4227

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/cbic.201300035

  • Stereoselective Synthesis of (E)-alpha,beta-Dehydroamino Acid Esters Reviewed

    Yasuno Yoko, Hamada Makoto, Yamada Takeshi, Shinada Tetsuro, Ohfune Yasufumi

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 10 )   1884 - 1888   2013.04( ISSN:1434-193X

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    DOI: 10.1002/ejoc.201300112

  • Using Stable Radicals To Protect Pentacene Derivatives from Photodegradation Reviewed

    Kawanaka Yusuke, Shimizu Akihiro, Shinada Tetsuro, Tanaka Rika, Teki Yoshio

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   52 ( 26 )   6643 - 6647   2013( ISSN:1433-7851

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/anie.201300595

  • Regioselective Prins Cyclization of Allenylsilanes. Stereoselective Formation of Multisubstituted Heterocyclic Compounds Reviewed

    Okada Takuya, Shimoda Airi, Shinada Tetsuro, Sakaguchi Kazuhiko, Ohfune Yasufumi

    ORGANIC LETTERS   14 ( 24 )   6130 - 6133   2012.12( ISSN:1523-7060

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    DOI: 10.1021/ol302669q

  • Efficient Synthesis of Anhydrorhodovibrin and Analogues Reviewed

    Yamada Takeshi, Okada Keiji, Shinada Tetsuro, Ohfune Yasufumi, Hashimoto Hideki

    SYNLETT   ( 20 )   2980 - 2984   2012.12( ISSN:0936-5214

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/s-0032-1317678

  • The Structure of (-)-Kaitocephalin Bound to the Ligand Binding Domain of the (S)-alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA)/Glutamate Receptor, GluA2 Reviewed

    Ahmed H. Ahmed, Hamada Makoto, Shinada Tetsuro, Ohfune Yasufumi, Weerasinghe Laksiri, Garner Philip P., Oswald Robert E.

    JOURNAL OF BIOLOGICAL CHEMISTRY   287 ( 49 )   41007 - 41013   2012.11( ISSN:0021-9258

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1074/jbc.M112.416362

  • TOTAL SYNTHESIS OF MANZACIDINS. AN OVERVIEW AND PERSPECTIVE Reviewed

    Ohfune Yasufumi, Oe Kentaro, Namba Kosuke, Shinada Tetsuro

    HETEROCYCLES   85 ( 11 )   2617 - 2649   2012.11( ISSN:0385-5414

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.3987/REV-12-746

  • Efficient total synthesis of manzacidin B Reviewed

    Shinada Tetsuro, Oe Kentaro, Ohfune Yasufumi

    TETRAHEDRON LETTERS   53 ( 26 )   3250 - 3253   2012.06( ISSN:0040-4039

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tetlet.2012.04.042

  • Stereoselective Total Syntheses of Insect Juvenile Hormones JH 0 and JH I Reviewed

    Manabe Atsushi, Ohfune Yasufumi, Shinada Tetsuro

    SYNLETT   ( 8 )   1213 - 1216   2012.05( ISSN:0936-5214

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/s-0031-1290803

  • Structure-activity relationship of novel juvenile hormone, JHSB(3), isolated from the stink bug, Plautia stali Reviewed

    Kaihara Kanako, Kotaki Toyomi, Numata Hideharu, Ohfune Yasufumi, Shinada Tetsuro

    TETRAHEDRON   68 ( 1 )   106 - 113   2012.01( ISSN:0040-4020

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tet.2011.10.080

  • Total synthesis of (-)-funebrine via Au-catalyzed regio- and stereoselective gamma-butyrolactonization of allenylsilane Reviewed

    Okada Takuya, Sakaguchi Kazuhiko, Shinada Tetsuro, Ohfune Yasufumi

    TETRAHEDRON LETTERS   52 ( 44 )   5744 - 5746   2011.11( ISSN:0040-4039

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    DOI: 10.1016/j.tetlet.2011.08.050

  • Au-catalyzed cyclization of allenylsilanes. Regioselective conversion to 2-amino-4-silylmethylene gamma-butyrolactone Reviewed

    Okada Takuya, Sakaguchi Kazuhiko, Shinada Tetsuro, Ohfune Yasufumi

    TETRAHEDRON LETTERS   52 ( 44 )   5740 - 5743   2011.11( ISSN:0040-4039

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tetlet.2011.07.144

  • Kaempferia parviflora Rhizome由来メトキシフラボンのキサンチンオキシダーゼ阻害活性および結晶構造(Xanthine Oxidase Inhibitory Activities and Crystal Structures of Methoxyflavones from Kaempferia parviflora Rhizome) Reviewed

    Nakao Kikuyo, Murata Kazuya, Deguchi Takahiro, Itoh Kimihisa, Fujita Takanori, Higashino Masayuki, Yoshioka Yuri, Matsumura Shin-ichi, Tanaka Rika, Shinada Tetsuro, Ohfune Yasufumi, Matsuda Hideaki

    (公社)日本薬学会 Biological & Pharmaceutical Bulletin   34 ( 7 )   1143 - 1146   2011.07( ISSN:0918-6158

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    ショウガ科生薬K.parviflora(KP)のキサンチンオキシダーゼ(XOD)阻害活性を調べた。KP根茎抽出物は他のショウガ科植物よりも強いXOD阻害活性を示した。KP抽出物からメトキシフラボン類を単離し、X線結晶構造解析を行い、XOD阻害活性を調べた。それらのうち3,5,7,4',5'-ペンタメトキシフラボンおよび3',4',5,7-テトラメトキシフラボンは阻害活性(IC50はそれぞれ0.9および>4mM)を示し、阻害様式は競合的/非競合的混合タイプであった。

  • Xanthine Oxidase Inhibitory Activities and Crystal Structures of Methoxyflavones from Kaempferia parviflora Rhizome Reviewed

    Nakao Kikuyo, Murata Kazuya, Deguchi Takahiro, Itoh Kimihisa, Fujita Takanori, Higashino Masayuki, Yoshioka Yuri, Matsumura Shin-ichi, Tanaka Rika, Shinada Tetsuro, Ohfune Yasufumi, Matsuda Hideaki

    BIOLOGICAL & PHARMACEUTICAL BULLETIN   34 ( 7 )   1143 - 1146   2011.07( ISSN:0918-6158

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  • Stereoselective anti-S(N)2 ' Mitsunobu reaction of alpha-hydroxy-alpha-alkenylsilanes Reviewed

    Higashino Masato, Ikeda Naoko, Shinada Tetsuro, Sakaguchi Kazuhiko, Ohfune Yasufumi

    TETRAHEDRON LETTERS   52 ( 3 )   422 - 425   2011.01( ISSN:0040-4039

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tetlet.2010.11.080

  • Biological activities of juvenile hormone III skipped bisepoxide in last instar nymphs and adults of a stink bug, Plautia stali Reviewed

    Kotaki Toyomi, Shinada Tetsuro, Kaihara Kanako, Ohfune Yasufumi, Numata Hideharu

    JOURNAL OF INSECT PHYSIOLOGY   57 ( 1 )   147 - 152   2011.01( ISSN:0022-1910

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.jinsphys.2010.10.003

  • Synthesis of C-13-Labeled 5,6,11-Trideoxytetrodotoxin Reviewed

    Umezawa Taiki, Shinada Tetsuro, Ohfune Yasufumi

    公益社団法人 日本化学会 CHEMISTRY LETTERS   39 ( 12 )   1281 - 1282   2010.12( ISSN:0366-7022

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    The synthesis of <sup>13</sup>C-labeled 5,6,11-trideoxytetrodotoxin has been successfully achieved. This is the first example of the <sup>13</sup>C-labeled analogs in tetrodotoxin congeners.

    DOI: 10.1246/cl.2010.1281

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  • Mild and Catalytic Transesterification Reaction Using K2HPO4 for the Synthesis of Methyl Esters Reviewed

    Shinada Tetsuro, Hamada Makoto, Miyoshi Kota, Higashino Masato, Umezawa Taiki, Ohfune Yasufumi

    SYNLETT   ( 14 )   2141 - 2145   2010.09( ISSN:0936-5214

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    DOI: 10.1055/s-0030-1258491

  • Synthesis and Absolute Structure of Manzacidin B (vol 9, pg 1765, 2007) Reviewed

    Shinada Tetsuro, Ikebe Eijiro, Oe Kentaro, Namba Kosuke, Kawasaki Masanori, Ohfune Yasufumi

    ORGANIC LETTERS   12 ( 9 )   2170   2010.05( ISSN:1523-7060

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    DOI: 10.1021/ol1006339

  • Total Synthesis of (-)-Amathaspiramide F Reviewed

    Tetrahedron   65   10355 - 10364   2010.04

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  • Mass Spectrometry Analysis of Peptides in the Brain Neruosecretory Cells and Nerohemal Organs in the Adult Blow Fyl, Protophormia terraenovae.

    Comp. Biochem. Physiol., Part A: Mol. Integ. Phys.   155   190 - 199   2010

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  • Total synthesis of (-)-amathaspiramide F Reviewed

    Sakaguchi Kazuhiko, Ayabe Miki, Watanabe Yusuke, Okada Takuya, Kawamura Kazushige, Shinada Tetsuro, Ohfune Yasufumi

    TETRAHEDRON   65 ( 50 )   10355 - 10364   2009.12( ISSN:0040-4020

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tet.2009.10.051

  • Structure Determination of a New Juvenile Hormone from a Heteropteran Insect Reviewed

    Kotaki Toyomi, Shinada Tetsuro, Kaihara Kanako, Ohfune Yasufumi, Numata Hideharu

    ORGANIC LETTERS   11 ( 22 )   5234 - 5237   2009.11( ISSN:1523-7060

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/ol902161x

  • Efficient Synthesis of (R)- and (S)-alpha-(Hydroxymethyl)pyroglutamic Acid Esters from L-Proline Reviewed

    Shinada Tetsuro, Yoshida Hiroki, Ohfune Yasufumi

    SYNTHESIS-STUTTGART   ( 22 )   3751 - 3756   2009.11( ISSN:0039-7881

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/s-0029-1217024

  • Efficient Total Synthesis of (-)-Kaitocephalin Reviewed

    Hamada Makoto, Shinada Tetsuro, Ohfune Yasufumi

    ORGANIC LETTERS   11 ( 20 )   4664 - 4667   2009.10( ISSN:1523-7060

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/ol9019343

  • Thiol addition to t-butyl methyl squarate. Efficient synthesis of novel sulfur-linked squaryl group-containing glutamate analogs Reviewed

    Shinada Tetsuro, Yamasaki Atsuko, kiniwa Yu-ichi, Shimamoto Keiko, Ohfune Yasufumi

    TETRAHEDRON LETTERS   50 ( 30 )   4354 - 4357   2009.07( ISSN:0040-4039

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tetlet.2009.05.037

  • Novel mastoparan and protonectin analogs isolated from a solitary wasp, Orancistrocerus drewseni drewseni Reviewed

    Murata Kazuya, Shinada Tetsuro, Ohfune Yasufumi, Hisada Miki, Yasuda Akikazu, Naoki Hideo, Nakajima Terumi

    AMINO ACIDS   37 ( 2 )   389 - 394   2009.07( ISSN:0939-4451

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1007/s00726-008-0166-y

  • An efficient total synthesis of kaitocephalin, a potent antagonist of iGluRs Reviewed

    Ohfune Yasufumi, Hamada Makoto, Shinada Tetsuro

    AMINO ACIDS   37 ( 1 )   87 - 87   2009.07( ISSN:0939-4451

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  • In vitro pharmacological activities of the extracts from red ant Formica aquilonia as potential therapeutic agents Reviewed

    Piao Chunhong, Tachikawa Eiichi, Hu Yaohui, SATO Yoshinori, YANG Ping, YAMAMOTO Kei-ichiro, SHINADA Tetsuro, SUZUKI Koichi

    和漢医薬学会 和漢医薬学雑誌   26 ( 2 )   61 - 67   2009( ISSN:18801447

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    中国長白山を産地とする赤アリ (<I>Formica aquilonia</I>) は, 関節リウマチやその他の疾病のための民間治療薬として活用されているが薬理学的な解析はまったくなされていない。 そこで, 乾燥赤アリの各種逐次抽出画分を用いながら, 細胞殺傷, 抗酸化, 抗炎症, prolyl oligopeptidase (POP) 活性阻害, カテコールアミン分泌阻害の 5 種類の活性を検討した。 その結果, ヘキサン抽出画分と酢酸エチル抽出画分に高い POP 活性が認められ, 酢酸エチル画分ではラット肝がん細胞 (dRLh84) に対して強い細胞殺傷性を示した。 また, cyclooxygenase (COX) 阻止による抗炎症アッセイにおいて, ヘキサンの上清画分で COX-1 に影響のない弱い COX-2 活性が認められた。 さらに, ウシ副腎クロム親和性細胞を利用したアセチルコリン依存性カテコールアミン分泌阻害は酢酸エチル画分で顕著であり, diphenylpierylhydrazyl アッセイによる抗酸化活性はアセトン画分で確認された。 以上の結果から, 民間治療薬としての薬理学的な解析を <I>in vitro</I> レベルで初めて明らかにしたもので, 赤アリ由来の生物薬剤開発に向けた物質同定とマウス実験の今後の必要性を提案している。

    DOI: 10.11339/jtm.26.61

    CiNii Article

  • In vitro Pharmacological Activities of Crude Extract from Red ant Formaica aquilonia as Potent Theraphutic Agents

    J. Traditional Med.   26   61 - 67   2009

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  • Thiol Addition to t-Butyl Methyl Squarate. Efficient Synthesis of Novel Sulfur-linked Squaryl Group Containing Glutamate Analogs.

    Tetrahedron Lett.   50   4354 - 4357   2009

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  • Short and Stereoselective Synthesis of (-)-Kaitocephalin,

    Org. Lett.   11   4664 - 4667   2009

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  • Efficient Synthesis of an Optically Active α-Hydroxymethylpyrroglutamic Acid.

    Synthesis   3751 - 3756   2009

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  • Structure Determination of a New Juvenile Hormone Isolated from a Heteropteran Insect.

    Org. Lett.   11   5234 - 5237   2009

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  • Short and stereoselective synthesis of manzacidins A and C, and their enantiomers Reviewed

    Oe Kentaro, Shinada Tetsuro, Ohfune Yasufumi

    TETRAHEDRON LETTERS   49 ( 52 )   7426 - 7429   2008.12( ISSN:0040-4039

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    DOI: 10.1016/j.tetlet.2008.10.074

  • Efficient Asymmetric Synthesis of Functionalized Pyroglutamate Core Unit Common to Oxazolomycin and Neooxazolomycin Using Michael Reaction of Nucleophilic Glycine Schiff Base with α,β-Disubstituted Acrylate.

    Tetrahedron: Asymmetry   19   2789 - 2795   2008

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  • Au(I)-Catalyzed Efficient Synthesis of α-Acyloxy-α'-silyl Ketones from α-Acyloxy-α-alkynylsilanes.

    Tetrahedron Lett.   49   25 - 28   2008

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  • A Quinone Isolated from the Nest of Vespa simillima and its Growth-Inhibitory Effect on Rat Liver Cancer Cells.

    Biol. Pharm. Bull.   31   722 - 755   2008

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  • Total Synthesis of (-)-Amathaspiramide F.

    Org. Lett.   10   5449 - 5452   2008

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  • Identification and localization of SIFamide in the pars intercerebralis of the blow fly Protophormia terraenovae Reviewed

    Shiga Sakiko, Inosaki Aoi, Numata Hideharu, Shinada Tetsuro, Ohfune Yasufumi, Yasuda Akikazu

    COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY B-BIOCHEMISTRY & MOLECULAR BIOLOGY   148 ( 3 )   350 - 350   2007.11( ISSN:1096-4959

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.cbpb.2007.07.069

  • Synthesis of Leucine-enkephalin analogs containing alpha-amino squaric acid Reviewed

    Shinada Tetsuro, Ishida Toshikazu, Hayashi Ken-ich, Yoshida Yasutaka, Shigeri Yasushi, Ohfune Yasufumi

    TETRAHEDRON LETTERS   48 ( 43 )   7614 - 7617   2007.10( ISSN:0040-4039

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    DOI: 10.1016/j.tetlet.2007.08.103

  • Synthesis of squaric acid-containing amino acid analogs Reviewed

    Ohfune Y., Yamazaki A., Ishida T., Shinada T.

    AMINO ACIDS   33 ( 3 )   LXV - LXV   2007.09( ISSN:0939-4451

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  • Synthesis and absolute structure of manzacidin B synthesis and absolute structure of manzacidin B Reviewed

    Shinada Tetsuro, Ikebe Eijiro, Oe Kentaro, Namba Kosuke, Kawasaki Masanori, Ohfune Yasufumi

    ORGANIC LETTERS   9 ( 9 )   1765 - 1767   2007.04( ISSN:1523-7060

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    DOI: 10.1021/ol0704789

  • Recent Progress on Squaric Acid Research in Bioorganic Fields Reviewed

    SHINADA Tetsuro, ISIDA Toshikazu, OHFUNE Yasufumi

    The Society of Synthetic Organic Chemistry, Japan, Journal of Synthetic Organic Chemistry, Japan   65 ( 1 )   30 - 43   2007.01( ISSN:00379980

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    Squaric acid belongs to a class of oxocarbons and exhibits unique physicochemical properties, e.g., strong acidity, aromaticity, strained ring, electron deficiency, and metal chelating ability. Squaric acid has received considerable attention as a carboxylic acid mimic in medicinal chemistry, a novel chromophore in material science, a new chelator in inorganic chemistry, and a building block of quinones, triquinanes, cyclopentenones, and furanones in organic synthesis. Recently, squaric acid diesters are employed for a variety of applications in scientific fields as a linker to construct novel bioconjugate molecules. This review will describes recent progress on the use of squaric acid focused on bioorganic research.

    DOI: 10.5059/yukigoseikyokaishi.65.30

    CiNii Article

  • Synthesis and Absolute Structure of Manzacidin B

    Org. Lett.   9   1765 - 1767   2007

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  • Novel Biologically Active Peptides from the Venom of Polistes rothneyi iwatai Reviewed

    Murata Kazuya, Shinada Tetsuro, Ohfune Yasufumi, HISADA Miki, YASUDA Akikazu, NAOKI Hideo, NAKAJIMA Terumi

    公益社団法人日本薬学会 Biological & pharmaceutical bulletin   29 ( 12 )   2493 - 2497   2006.12( ISSN:09186158

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    Four novel peptides, polistes-mastoparan-R1, 2, 3, and polistes-protonectin, were isolated from the venom of a paper wasp, <i>Polistes rothneyi iwatai</i>. MALDI-TOF MS analysis of a small amount of the crude venom gave six molecular-related ion peaks. Among them, <i>m</i>/<i>z</i> 1565 was expected to be a novel peptide. Purification of the crude venom by HPLC gave two known kinins, Thr<sup>6</sup>-bradykinin and Ala-Arg-Thr<sup>6</sup>-bradykinin, and four novel peptides named polistes-mastoparan-R1, 2, and 3, and polistes-protonectin. Polistes-mastoparan-R1, 2, and 3 (Pm-R) were tetradecapeptides that possess high sequence homology with that of mastoparan. The sequence of polistes-protonectin was similar to that of protonectin isolated from a Brazilian paper wasp. Histamine-releasing activities of Pm-R1, 2, and 3 were more potent than that of mastoparan. Polistes-protonectin exhibited the most potent hemolytic activity in comparison with the four novel peptides and mastoparan.

    DOI: 10.1248/bpb.29.2493

    CiNii Article

  • Total synthesis of (-)-5,6,11-trideoxytetrodotoxin and its 4-epimer Reviewed

    Umezawa Taiki, Hayashi Toshihiro, Sakai Hiroshi, Teramoto Hidetoshi, Yoshikawa Takeshi, Izumida Masashi, Tamatani Yoshinori, Hirose Tadashi, Ohfune Yasufumi, Shinada Tetsuro

    ORGANIC LETTERS   8 ( 21 )   4971 - 4974   2006.10( ISSN:1523-7060

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    DOI: 10.1021/ol062098d

  • On the Stereoselectivity of Asymmetric Strecker Synthesis in a Cyclohexane System : Synthesis of Optically Active cis- and trans-1-Amino-2-hydroxycyclohexane-1-carboxylic Acids Reviewed

    Shinada Tetsuo, Kawakami Tadashi, Sakai Hiroshi, MATSUDA Hiromi, UMEZAWA Taiki, KAWASAKI Masaki, NAMBA Kosuke, OHFUNE Yasufumi

    Chemical Society of Japan Bulletin of the Chemical Society of Japan   79 ( 5 )   768 - 774   2006.05( ISSN:00092673

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    CiNii Article

  • A new entry for the synthesis of N-acyl-N '-substituted guanidines Reviewed

    Shinada T, Umezawa T, Ando T, Kozuma H, Ohfune Y

    TETRAHEDRON LETTERS   47 ( 12 )   1945 - 1947   2006.03( ISSN:0040-4039

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    DOI: 10.1016/j.tetlet.2006.01.065

  • A New Entry to the Synthesis of N-Acylguanidine by Condensation of Thiocarbamates with HMDS

    Tetrahedron Lett.   47   1945 - 1947   2006

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  • On the Stereoselectivity of the Asymmetric Transferring Strecker Synthesis in a Cyclohexane System: Synthesis of Optically Active Cis- and Trans-1-amino-2-hydroxycyclohexane-1-carboxylic Acids.

    Bull. Chem. Soc. Jpn.   79   768 - 774   2006

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  • Stereoselective synthesis of 2,5-DI- and 2,2,5-trisubstituted pyrrolidines by allylation reaction of acyliminium ion Reviewed

    Shinada T, Hamada M, Kawasaki M, Ohfune Y

    HETEROCYCLES   66   511 - 525   2005.12( ISSN:0385-5414

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  • Enantio- and diastereoselective construction of alpha,alpha-disubstituted alpha-amino acids for the synthesis of biologically active compounds Reviewed

    Ohfune Y, Shinada T

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 24 )   5127 - 5143   2005.12( ISSN:1434-193X

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    DOI: 10.1002/ejoc.200500434

  • Syntheses of alpha-amino squaric acids using an aminomalonate equivalent bearing a squaryl group Reviewed

    Ishida T, Shinada T, Ohfune Y

    SYNTHESIS-STUTTGART   ( 16 )   2723 - 2729   2005.10( ISSN:0039-7881

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/s-2005-872109

  • Total synthesis of (-)-kaitocephalin Reviewed

    Kawasaki M, Shinada T, Hamada M, Ohfune Y

    ORGANIC LETTERS   7 ( 19 )   4165 - 4167   2005.09( ISSN:1523-7060

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/ol0515154

  • Molecular components and toxicity of the venom of the solitary wasp, Anoplius samariensis Reviewed

    Hisada M, Satake H, Masuda K, Aoyama M, Murata K, Shinada T, Iwashita T, Ohfune Y, Nakajima T

    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS   330 ( 4 )   1048 - 1054   2005.05( ISSN:0006-291X

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    DOI: 10.1016/j.bbrc.2005.03.087

  • Indium-mediated asymmetric barbier-type allylation of aldimines in alcoholic solvents: Synthesis of optically active homoallylic amines Reviewed

    Vilaivan T, Winotapan C, Banphavichit V, Shinada T, Ohfune Y

    JOURNAL OF ORGANIC CHEMISTRY   70 ( 9 )   3464 - 3471   2005.04( ISSN:0022-3263

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/jo0477244

  • Synthesis of novel amino squaric acids via addition of dianion enolates derived from N-boc amino acid esters Reviewed

    Ishida T, Shinada T, Ohfune Y

    TETRAHEDRON LETTERS   46 ( 2 )   311 - 314   2005.01( ISSN:0040-4039

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    DOI: 10.1016/j.tetlet.2004.11.044

  • Indium-mediated Asymmetric Barbier-type Allylation of Aldimines in Alcoholic Solvents: Synthesis of Optically Active Homoallylic Amines

    Journal of Organic Chemisty   70   3464 - 3471   2005

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  • Synthesis of α-Amino Squaric Acids Using an Aminomalonate Equivalent Bearing Squaryl Group

    Synthesis   in press   2005

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  • Total Syntheis of (-)-Kaitocephalin

    Organic Letters   in press   2005

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  • Rapid and efficient identification of cysteine-rich peptides by random screening of a venom gland cDNA library from the hexathelid spider Macrothele gigas

    Toxicon   44   149 - 156   2004

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  • Synthesis of Optically Active α-Alkyl Aspartate via [3,3] Sigmatropic Rearrangement of α-Acyloxytrialkylsilane

    Tetrahedron Letters   45   5869 - 5872   2004

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  • Efficient synthesis of optically active a-substituted glutamate analogs possessing a-hydroxymethyl and a-alkoxymethyl groups

    Tetrahedron Lett.   44   1235 - 1238   2003

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  • Syntheses and Paralytic Activities of Squaryl Amino Acid-Containing Polyamine Toxins

    Amino Acids   24   293 - 302   2003

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  • Stereoselective construction of the tetraol part in tetrodotoxin using epxidation and ring opening strategy of allyl sulfone.

    Synlett   619 - 622   2003

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  • 昆虫特異的機能器官に含まれる生理活性物質探索の新機軸:狩りバチ由来昆虫麻痺分子の探索研究

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    東北蚕糸・昆虫利用研究報告第28号   1 - 2   2003

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  • Asymmetric Strecker Route toward the Synthesis of Biologically Active a,a-Disubstituted a-Amino Acids

    Bull. Chem. Soc. Jpn.   76   1115 - 1129   2003

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  • Stereocontrolled synthesis of a potent agonist of Group II metabotropic glutamate receptors, (+)-LY354740, and its related derivatives

    Tetrahedron Lett. .   44   5431 - 5434   2003

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  • 1,2-Dioxo-3-isopropyl-4-methyl-3-cyclobutene as a Nucleophilic Synthon. Synthesis of Sq-containing Cinnamic Acid Derivatives.

    Shinada, T., Ooyama, Y., Hayashi, K., Ohfune, Y.

    Tetrahedron Lett.   43   6755 - 6758   2002

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  • Syntheses of Gabosine A, B, D, and E from Allyl Sulfide Derived from (-)-Quinic Acid.

    Synlett   1341 - 1343   2002

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  • Bacteriorhodopsin Analog Regenerated with 13-Desmethyl-13-iodoretinal

    Biophysical J.   83   3460 - 3469   2002

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  • Indium mediated barbier-type allylation of aldimines in alcoholic solvents

    Tetrahedron Letters   42   in press   2001

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  • Radical homologation of d-gluconic acid: highly diastereoselective synthesis of D-gluco-KDO derivative

    Tetrahedron   57   8767 - 8771   2001

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  • Novel and Efficient Transformation of α-Amino Nitrile to α-Imino Nitrile and α-amide Nitriles in Asymmetric Strecker Synthesis

    Tetrahedron Letters   42   3733 - 3736   2001

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  • Efficient Synthesis of EDO-S,S-DMEDT-TTF, a Potent Organic-Donor for Synthetic Metal

    Synlett   1476 - 1478   2001

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  • Total Synthesis and Absolute Structure of Manzasidin A and C

    Journal of the American Chemical Society   112   10708 - 10709   2000

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  • Asymmetric Strecker Route toward the Corey Intermediate of Lactacystin.

    Synlett   1631 - 1633   2000

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  • Squaric Acid Derivatives Prevent the Removal of N-Cbz and N-Fmoc Groups under Catalytic Hydrogenation Reaction

    Synlett   1506 - 1509   2000

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  • Stereoselective Synthesis of 9-trans-9-Desmethyl-9-flnororetinals Based on the Four-Components Coupling Approach

    Tetrahedron   55 ( 12 )   3675 - 3686   1999

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  • Efficient Synthesis of a Novel 4-Hydroxy-2,3-dioxocyclobut-1-enyl Group Containing Amino Acids

    Organic Letters   1   1633 - 1666   1999

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  • An Efficient Synthesis of a-Acyloxyketone by Cu(acac)2-catalyzed Insertion Reaction of Diazoketone to Carboxylic Acid

    Tetrahedron Letters   39   3757 - 3760   1998

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  • Direct Conversion of 1,2-Diol into Ally Sulfide. Regioselective Transformation of (-)-Quinic Acid to (-)-Shikimic Acid

    Tetrahedron Letters   39   6027 - 6028   1998

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  • Olefination of Dialkyl Squarates by Wittig and Horner-Emmons Reactions. A Facile Synthesis of 3,4-Dioxo-1-cyclobutene-1-acetic Acid Esters.

    Tetrahedron Letters   38   7091 - 7094   1997

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  • Stereoselective Functionalization at C-9 of Retinal: Synthesis of 9-trans-19-nor-9-Haloretinal Analogs

    Chemistry and Pharmaceutical Bulletin   44   264 - 266   1996

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  • The Invention of Radical Reactions. Part XXXVI. Synthetic Studies Related to 3-Deoxy-D-manno-2-octulosonic acid (KDO)

    Tetrahedron   52   2717 - 2726   1996

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  • Facile Synthesis of 6-Hydroxyindole-3-acetic acid: On the Structure of the Aromatic Subunit of Nephilatoxin-1~6

    Tetrahedron Letters   37   7099 - 7102   1996

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  • Oxidation of Hydrazones by Hypervalent Organoiodine Reagents: Regeneration of Carbonyl Group and Facile Synthesis of a-acetoxy and a-alkoxy azo Compounds

    Tetrahedron   52   2717 - 2726   1996

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  • Interaction of Tryptophan-182 with the Retinal 9-Methyl Group in the L Intermediate of Bacteriorhodopsin

    Biochemistry   34   577 - 582   1995

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  • Biosynthesis of Phytosiderophores, Mugineic Acids, Associated with Methionine Cycling

    Journal of Biological Chemistry   270   16549 - 16554   1995

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  • Stereocontrolled Functionalization at the C-9 of Retinal. Stereoselective Synthesis of 9-trans-9-Fluororetinal

    Synlett   1247 - 1248   1995

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  • A Facile Method for the Conversion of Oximes to Ketones and Aldehydes by the Use of Activated MnO2

    Tetrahedron Letters   36   6701 - 6704   1995

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  • An Efficient Method for Removal of Chiral Auxiliaries, Camphorsultam and 4-Isopropyl-2- oxazolidinone

    Synlett   637 - 638   1994

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    Publishing type:Research paper (scientific journal)  

  • Stereoselective Addition of 2-Aminothiophenol to α-Alkoxycinnamic Acid Derivatives--Alternative Synthesis of Diltiazem--

    Tetrahedron   49   8119 - 8128   1993

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    Publishing type:Research paper (scientific journal)  

  • Oxidation of Phenylhydrazones of α-Keto Esters with Hypervalent Organoiodine Reagents

    Tetrahedron Letters   34   7191 - 7194   1993

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    Publishing type:Research paper (scientific journal)  

  • Chain-elongation and Degradation of Carboxylic Acids by Barton-ester Based Radical Chemistry

    Tetrahedron Letters   34   6505 - 6508   1993

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    Publishing type:Research paper (scientific journal)  

  • A New Stereoselective Route to γ-Butyrolactones : Asymmetric Synthesis of(+)-trans-Whisky and (+)-Cognac Lactones

    Chemistry and Pharmaceutical Bulletin   40   2579 - 2581   1992

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  • Asymmetric Induction at Two Contiguous Stereogenic Centers by Diastereoface Differentiating Nucleophilic Addition Reaction

    Tetrahedron Letters   32   3519 - 3522   1991

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  • Stereospecific Nucleophilic Addition Reaction to Olefins--Addition of Thiols α,β-Unsaturated to Carboxylic Acid Derivatives

    Journal of Organic Chemistry   56   6556 - 6564   1991

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    Publishing type:Research paper (scientific journal)  

  • Synthesis of Fluorine Analogues of Protoporphyrin Potentially Useful for Diagnosis and Therapy of Tumors

    Chemistry and Pharmaceutical Bulletin   38   2175 - 2178   1990

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    Publishing type:Research paper (scientific journal)  

  • Facile Conversion of(Z)-2-Alkenoic Esters into the(E)-Isomers with Diphenyl Disulfide

    Synthesis   1123 - 1125   1990

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  • Synthesis of Corynanthe Alkaloids Corynantheine, Hirsuteine and the Isositsirikines

    Heterocycles   30   1031 - 1077   1990

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  • Stereoselective Isomerization of Ethylidene Lactam for the Synthesis of Z-Isositsirikines

    Tetrahedron Letters   30   2941 - 2944   1989

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  • Stereospecific Nucleophilic Addition Reaction of Thiophenol to α,β-Unsaturated Esters

    Chemistry and Pharmaceutical Bulletin   37   3158 - 3160   1989

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  • Synthesis of Corynantheine Alkaloids with(19E)-Ethylidene Group : on the Structures of Rhazimanine and Bhimberine

    Heterocycles   27   1603 - 1606   1988

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    Publishing type:Research paper (scientific journal)  

  • Synthesis of Fluorine Analogs of Protoporphyrin

    Journal of Fluorine Chemistry   42   293 - 298   1988

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Books and Other Publications

  • 化学の要点シリーズ43 海洋天然物化学

    品田哲郎・保野陽子( Role: Contributor ,  第2章 海洋天然物の草分け カイニン酸)

    日本化学会  2023.08  ( ISBN:9784320044845

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    Total pages:148   Responsible for pages:7   Book type:Textbook, survey, introduction

    Other Link: https://www.chemistry.or.jp/journal/books/expert/43.html

  • ドラマチック有機合成化学 感動の瞬間 Reviewed

    ( Role: Contributor ,  超微量天然有機化合物の構造決定)

    化学同人  2023.07  ( ISBN:978-4-7598-2336-3

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    Total pages:206   Responsible for pages:2   Book type:General book, introductory book for general audience

  • Neuroprotective Properties of the Fungus Isaria Japonica: Evidence from a Mouse Model of Aged Related Degeneration

    K. Suzuki, M. Tsushima1, M. Goryo, T. Shinada, Y. Yasuno, E. Nishimura, Y.Terayama, Y. Mori, Y. Yoshioka( Role: Joint author)

    Frontiers in Clinical Drug Research-Alzheimer Disorder; Vol. 2, Bentham e-Books series  2017.04  ( ISBN:978-1-68108-340-7

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    Total pages:250   Responsible for pages:33   Book type:Scholarly book

MISC

  • 重水素化アルデヒドの簡便合成 Reviewed

    品田哲郎, 熊懐克志, 橘和航平, 小澤圭太, 田村優作, 山本悠生, 中山淳, 岡村仁則, 保野陽子

    創薬懇話会講演要旨集   2021   2021

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    Publishing type:Article, review, commentary, editorial, etc. (scientific journal)  

    J-GLOBAL

  • Analysis of the iron-sulfur cluster present in the active center of mevalonate phosphate dehydratase from hyperthermophilic archaea Reviewed

    米山睦, 三野広幸, 保野陽子, 品田哲郎, 吉村徹, 邊見久

    日本農芸化学会大会講演要旨集(Web)   2021   2021( ISSN:2186-7976

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  • トリテルペン/セスクアテルペン環化酵素の立体構造解析 Reviewed

    亀谷太一, 久保田智巳, 品田哲郎, 上田大次郎, 佐藤努

    イソプレノイド研究会例会講演要旨集   31st (CD-ROM)   2021

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  • ホモプシンAの全合成研究 Reviewed

    保野陽子, 苅田祐馬, 丸林聖司, 品田哲郎, 大石徹

    有機合成シンポジウム講演要旨集   118th   2021

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  • Enzymatic study of trans-anhydromevalonate phosphate decarboxylase, a key enzyme of the archaeal mevalonate pathway Reviewed

    松嶋夏海, 栗木莉子, 保野陽子, 品田哲郎, 吉村徹, 邊見久

    日本農芸化学会大会講演要旨集(Web)   2021   2021( ISSN:2186-7976

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  • Biosynthetic study of bibenzyl cannabinoids from Radula perrottetii Reviewed

    田浦太志, 高橋宏暢, 兼目裕充, 浅川義範, 保野陽子, 品田哲郎

    日本農芸化学会大会講演要旨集(Web)   2021   2021( ISSN:2186-7976

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  • Development of synthetic transformation using acyl carbazole Reviewed

    品田哲郎, 落合紫帆, KANG Bubwoong, 岡村仁則, 保野陽子, 臼杵克之助, 佐藤哲也

    複素環化学討論会講演要旨集   50th   2021

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  • アーキア型メバロン酸経路の鍵酵素であるホスホメバロン酸脱水酵素は[4Fe-4S]型鉄硫黄クラスターを有する Reviewed

    米山睦, 三野広幸, 保野陽子, 品田哲郎, 伊藤智和, 邊見久

    日本Archaea研究会講演会要旨集   33rd (CD-ROM)   2021

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  • クラスIB大型テルペン合成酵素の基質複合体の結晶構造 Reviewed

    金本壮平, 佐藤努, 品田哲朗, 三木邦夫, 深井周也, 藤橋雅宏

    日本結晶学会年会講演要旨集   2020 (CD-ROM)   2020

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  • Characterization of phosphomevalonate dehydratase involved in the archaeal mevalonate pathway Reviewed

    米山睦, 齋藤甲斐, 保野陽子, 品田哲郎, 吉村徹, 邊見久

    日本農芸化学会大会講演要旨集(Web)   2020   2020( ISSN:2186-7976

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  • クラスIBテルペン合成酵素の触媒反応の解析 Reviewed

    西智之, STEPANOVA Rafaella, 菅原啓, 上田大次郎, 藤橋雅宏, 三木邦夫, 保野陽子, 品田哲郎, 佐藤努

    日本農芸化学会大会講演要旨集(Web)   2019   2019( ISSN:2186-7976

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  • Analysis of ligand-recognition mechanism of class IB terpene synthase Reviewed

    稲木隼人, 佐藤努, 保野陽子, 品田哲郎, 三木邦夫, 藤橋雅宏

    量子ビームサイエンスフェスタ(Web)   2018   2019

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  • Class IB大型テルペン合成酵素の基質認識機構の解析 Reviewed

    藤橋雅宏, 稲木隼人, 西智之, 上田大次郎, 佐藤努, 品田哲朗, 三木邦夫

    イソプレノイド研究会例会講演要旨集   29th   2019

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  • 新規ファミリーに属するテルペン合成酵素の基質認識部位の同定

    稲木隼人, 佐藤努, 保野陽子, 品田哲郎, 三木邦夫, 藤橋雅宏

    日本結晶学会年会講演要旨集   2018   62   2018.11

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  • Large‐terpene合成酵素の酵素的諸性質の解析と部位特異的変異 Reviewed

    西智之, 菅原啓, 小川佳央, 高橋宏忠, 上田大次郎, 藤橋雅宏, 三木邦夫, 保野陽子, 品田哲郎, 佐藤努

    日本蛋白質科学会年会プログラム・要旨集   18th   50   2018.05

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  • 単体ボヤCnemidocarpa ireneより得られた芳香族化合物群の構造と機能 Reviewed

    宮古圭, 保野陽子, 品田哲郎, 藤田雅紀, 酒井隆一

    日本水産学会大会講演要旨集   2018   108   2018.03

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  • UPLC‐MS/MSを用いたカメムシ類の幼若ホルモンの構造決定 Reviewed

    松本圭司, 児玉彩, 小滝豊美, 品田哲郎, 後藤慎介

    日本応用動物昆虫学会大会講演要旨   62nd   190   2018.03

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  • 酸触媒によるα‐ヒドロキシ‐α‐アルケニルシランの不斉転写型分子内Friedel‐Crafts反応 Reviewed

    久保田駿一, 赤木航, 池田直子, 東野勝人, 品田哲郎, 大船泰史, 西村貴洋, 坂口和彦

    日本化学会春季年会講演予稿集(CD-ROM)   98th   ROMBUNNO.4H4‐17   2018.03

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  • Large‐terpene合成酵素の結晶構造解析 Reviewed

    藤橋雅宏, 佐藤努, 田中勇真, 山本大輔, 西智之, 上田大次郎, 村上瑞気, 保野陽子, 関原あい, 福和真, 品田哲郎, 三木邦夫

    日本農芸化学会大会講演要旨集(Web)   2018   ROMBUNNO.3A17p01 (WEB ONLY)   2018.03( ISSN:2186-7976

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  • Large‐terpene合成酵素の酵素的諸性質の解析と部位特異的変異 Reviewed

    菅原啓, 西智之, 小川佳央, 高橋宏忠, 上田大次郎, 藤橋雅宏, 三木邦夫, 保野陽子, 品田哲郎, 佐藤努

    日本農芸化学会大会講演要旨集(Web)   2018   ROMBUNNO.3A17p02 (WEB ONLY)   2018.03( ISSN:2186-7976

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  • ジアミノジカルボン酸類の触媒的不斉合成 Reviewed

    保野陽子, 水谷衣穂, 末内優輝, 品田哲郎

    メディシナルケミストリーシンポジウム講演要旨集   35th   155   2017.10( ISSN:0919-214X

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  • Cirratiomycin類の全合成 Reviewed

    保野陽子, 西村彰人, 澤井瑛, 品田哲郎

    有機合成シンポジウム講演要旨集   111th   30‐31   2017.05

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  • カメムシ類の幼若ホルモン:クサギカメムシおよびタガメの場合 Reviewed

    小滝豊美, 後藤慎介, 松本圭司, 品田哲郎, 志賀向子, 門司麻衣子, 沼田英治

    日本応用動物昆虫学会大会講演要旨   61st   85   2017.03

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  • シクロラバンデュリル二リン酸合成酵素の結晶構造解析 Reviewed

    小林正弥, 富田武郎, 品田哲郎, 西山真, 葛山智久

    日本農芸化学会大会講演要旨集(Web)   2017   ROMBUNNO.2C11p10 (WEB ONLY)   2017.03( ISSN:2186-7976

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  • カメムシから見つかった新規幼若ホルモンの構造決定:構造推理を出発点とする超微量天然物の構造決定 Reviewed

    品田 哲郎, 保野 陽子, 小滝 豊美

    公益社団法人 日本農芸化学会 化学と生物   56 ( 1 )   10 - 12   2017( ISSN:0453-073X

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  • シクロラバンデュリル2リン酸合成酵素の結晶構造解析 Reviewed

    小林正弥, 富田武郎, 品田哲郎, 西山真, 葛山智久

    イソプレノイド研究会例会講演要旨集   26th   11   2016.09

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  • ラジカル環化反応による3置換‐4,5‐ジヒドロピロール類の合成 Reviewed

    山田梓紗, 品田哲郎

    複素環化学討論会講演要旨集   46th   51‐52   2016.09

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  • 認知症薬を目指す(1):カイコ冬虫夏草の安全性試験 Reviewed

    シラパコング ピヤマース, 石黒慎一, 苅間澤真弓, 江幡真規子, 御領政信, 佐々木淳, 小田伸一, 西村栄治, 品田哲郎, 鈴木幸一

    日本蚕糸学会大会・蚕糸・昆虫機能学術講演会講演要旨集   86th   41   2016.03

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  • 海洋性カロテノイドであるフコキサンチンの類縁体(パラセントロン)のフェムト秒時間分解吸収分光 Reviewed

    橋本秀樹, 行平奈央, 藤原正澄, 西岡勇人, 品田哲郎, 坂口和彦, 勝村成雄

    日本化学会春季年会講演予稿集(CD-ROM)   96th   ROMBUNNO.3PA‐143   2016.03

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  • Moorella thermoacetica由来テトラプレニル‐β‐クルクメン合成酵素ホモログのゲノムマイニング Reviewed

    藤井友里恵, 田中勇真, 藤橋雅宏, 三木邦夫, 河合優人, 中島田豊, 品田哲郎, 佐藤努

    日本農芸化学会大会講演要旨集(Web)   2016   2B022 (WEB ONLY)   2016.03( ISSN:2186-7976

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  • 放線菌由来ジテルペン環化酵素CotB2が触媒する精巧な環化反応機構の解明 Reviewed

    寺本和矢, 目黒亜由子, 本吉祐大, 佐藤玄, 佐藤玄, 増本優衣, 増本優衣, 手塚則亨, 手塚則亨, 坂井健太, 上田翔太, 遠塚悠輔, 安藤祐美, 富田武郎, KIM Seung‐Young, 木村智之, 五十嵐雅之, 澤竜一, 品田哲郎, WANG Chao, WANG Chao, 内山真伸, 内山真伸, 西山真, 葛山智久

    日本農芸化学会大会講演要旨集(Web)   2016   4B026 (WEB ONLY)   2016.03( ISSN:2186-7976

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  • 非造礁性六射サンゴの紫外線吸収物質の特性 Reviewed

    平井もも, 江崎洋一, 品田哲郎, 竹中大輝, 千徳明日香, 千徳明日香

    日本古生物学会例会講演予稿集   165th   49   2016.01

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  • 双性イオン 1,3-ジアキシアル反発 幼若ホルモン 両親媒性ポリマー Reviewed

    松尾 淳一, 佐藤 隆章, 品田 哲郎, 大迫 隆男

    社団法人 有機合成化学協会 有機合成化学協会誌   74 ( 6 )   645 - 645   2016

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  • 最新の生物毒の多様性がおもしろい! その構造と機能、進化そして利用について 昆虫毒 その多様性と選択性 Reviewed

    品田 哲郎

    (公社)日本生化学会, 日本生化学会大会・日本分子生物学会年会合同大会講演要旨集   88回・38回   [1W9 - 3]   2015.12

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  • テトロドトキシンの触媒的不斉全合成研究 Reviewed

    上田翔太, 真鍋敦, 品田哲郎

    複素環化学討論会講演要旨集   45th   295 - 296   2015.11

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  • テルペン環化がおもしろい! 驚きの連続反応機構と新規環化触媒 Reviewed

    保野陽子, 品田哲郎

    化学   70 ( 10 )   66 - 67   2015.10( ISSN:0451-1964

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  • Bacillus clausiiにおけるセスタテルペン,Head‐to‐tail型トリテルペン,セスクアテルペンの生合成:多機能性酵素の同定とイソプレノイド代謝物の解析 Reviewed

    上田大次郎, 山鹿宏彰, 村上瑞気, 遠塚悠輔, 品田哲郎, 佐藤努

    (公社)日本生物工学会, 日本生物工学会大会講演要旨集   67th   338 - 338   2015.09

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  • カイコ冬虫夏草に由来する海馬修復因子の精製と機能解析 Reviewed

    石黒慎一, SILLAPAKONG Piyamas, 苅間澤真弓, 江幡真規子, 佐々木謙吾, 高橋真奈美, 漆畑拓弥, 若林篤光, 松浦哲也, 品田哲郎, 鈴木幸一

    日本蚕糸学会大会・蚕糸・昆虫機能学術講演会講演要旨集   85th   70   2015.09

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  • Bacillus clausiiにおけるセスタテルペン,head‐to‐tailトリテルペンおよびセスクアテルペンの生合成:多機能性酵素の同定とイソプレノイド代謝物の解析 Reviewed

    上田大次郎, 山鹿宏彰, 村上瑞気, 遠塚悠輔, 品田哲郎, 佐藤努

    イソプレノイド研究会例会講演要旨集   25th   10   2015.09

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  • アリル基質同士の縮合と環化反応を触媒する新奇テルペン合成酵素の発見 Reviewed

    小林正弥, 尾崎太郎, 趙平, 富田武郎, 苅田祐馬, 保野陽子, 西村栄治, 品田哲郎, 西山真, 葛山智久

    イソプレノイド研究会例会講演要旨集   25th   11   2015.09

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  • 放線菌由来ジテルペン環化酵素CotB2の特異な環化反応機構の解明 Reviewed

    寺本和矢, 目黒亜由子, 本吉祐大, 上田翔太, 遠塚悠輔, 安藤祐美, 坂井健太, 富田武郎, 金承榮, 木村智之, 五十嵐雅之, 澤竜一, 品田哲郎, 西山真, 葛山智久

    イソプレノイド研究会例会講演要旨集   25th   13   2015.09

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  • Bacillus clausiiにおけるセスタテルペン,Head‐to‐tail型トリテルペン,セスクアテルペンの生合成:多機能性酵素の同定とイソプレノイド代謝物の解析 Reviewed

    上田大次郎, 山鹿宏彰, 村上瑞気, 遠塚悠輔, 品田哲郎, 佐藤努

    香料・テルペンおよび精油化学に関する討論会講演要旨集   59th   148 - 150   2015.09

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  • デオキシペリジニンの合成研究 Reviewed

    坂口和彦, 木梨尚人, 西岡勇人, 奥菜津未, 鳥山陽平, FRANK Harry A., 勝村成雄, 品田哲郎

    香料・テルペンおよび精油化学に関する討論会講演要旨集   59th   253 - 255   2015.09

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  • 共役ケトンを有するアポカロテノイド類の全合成研究 Reviewed

    西岡勇人, 矢野陽, 木梨尚人, 奥菜津未, 鳥山陽平, 勝村成雄, 品田哲郎, 坂口和彦

    香料・テルペンおよび精油化学に関する討論会講演要旨集   59th   105 - 107   2015.09

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  • 3P-269 Biosynthesis of rare terpenoids in Bacillus clausii Reviewed

    Ueda Daijiro, Yamaga Hiroaki, Murakami Mizuki, Totsuka Yusuke, Shinada Tetsuro, Sato Tsutomu

    日本生物工学会, 日本生物工学会大会講演要旨集   67   2015

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  • Cirratiomycin Aの全合成 Reviewed

    西村彰人, 安川佳史, 保野陽子, 大船泰史, 品田哲郎

    天然有機化合物討論会講演要旨集(Web)   57th   543‐548(J‐STAGE)   2015( ISSN:2433-1856

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  • 昆虫毒:その多様性と選択性 Reviewed

    品田哲郎

    日本生化学会大会(Web)   88th   1W9-3 (WEB ONLY)   2015

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  • クロスカップリングに有用な新規アルキニルスズの開発とペリジニン類の効率的合成研究 Reviewed

    木梨尚人, 坂口和彦, 小澄大輔, 橋本秀樹, 品田哲郎, 勝村成雄

    香料・テルペンおよび精油化学に関する討論会講演要旨集   58th   279 - 281   2014.09

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  • プロポリス由来,新規テトラアルキルPhloroglucinol類の構造決定―1 Reviewed

    西村栄治, 品田哲郎, 大船泰史, 鈴木幸一

    香料・テルペンおよび精油化学に関する討論会講演要旨集   58th   191 - 193   2014.09

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  • プロポリス由来,新規テトラアルキルPhloroglucinol類の構造決定―2 Reviewed

    西村栄治, 品田哲郎, 大船泰史, 鈴木幸一

    香料・テルペンおよび精油化学に関する討論会講演要旨集   58th   194 - 196   2014.09

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  • Furan Diels‐Alder反応を鍵とするテトロドトキシンの全合成研究 Reviewed

    真鍋敦, 上田翔太, 品田哲郎

    複素環化学討論会講演要旨集   44th   89 - 90   2014.08

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  • グルタミン酸アナログ類の昆虫麻痺活性とグルタミン酸受容体サブタイプ選択性 Reviewed

    品田哲郎, 山嵜敦子, 大船泰史

    トキシンシンポジウム予稿集   61st   115 - 119   2014.08( ISSN:1344-9346

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  • C60を超える長鎖イソプレノイドの合成研究 Reviewed

    遠塚悠輔, 上田翔太, 品田哲郎

    日本化学会講演予稿集   94th ( 4 )   1482   2014.03( ISSN:0285-7626

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  • シクロプロパン環を導入した2,6‐ジアミノピメリン酸誘導体の立体選択的合成 Reviewed

    安尾望, 島本啓子, 大船泰史, 品田哲郎

    日本化学会講演予稿集   94th ( 4 )   1469   2014.03( ISSN:0285-7626

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  • アクロメリン酸類の合成研究 Reviewed

    御前公美, 品田哲郎, 大船泰史

    日本化学会講演予稿集   94th ( 4 )   1456   2014.03( ISSN:0285-7626

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  • α‐アミノスクアリン酸を導入したCaspase‐3阻害ペプチドの合成 Reviewed

    前田健太郎, 大船泰史, 品田哲郎

    日本化学会講演予稿集   94th ( 4 )   1470   2014.03( ISSN:0285-7626

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  • Triumphaloneの立体選択的全合成 Reviewed

    西村栄治, 大船泰史, 品田哲郎

    日本化学会講演予稿集   94th ( 4 )   1482   2014.03( ISSN:0285-7626

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  • Cirratiomycin Aの合成研究 Reviewed

    西村彰人, 保野陽子, 品田哲郎

    日本化学会講演予稿集   94th ( 4 )   1470   2014.03( ISSN:0285-7626

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  • テトロドトキシンの短段階合成研究 Reviewed

    真鍋敦, 上田翔太, 大船泰史, 品田哲郎

    日本化学会講演予稿集   94th ( 4 )   1468   2014.03( ISSN:0285-7626

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  • 芳香環上に側鎖を持つカイトセファリンアナログの合成研究 Reviewed

    吉田侑矢, 保野陽子, 大船泰史, 品田哲郎

    日本化学会講演予稿集   94th ( 4 )   1457   2014.03( ISSN:0285-7626

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  • 分子内ラジカル環化を用いたカイノイド類の合成研究 Reviewed

    山田梓紗, 大船泰史, 品田哲郎

    日本化学会講演予稿集   94th ( 4 )   1456   2014.03( ISSN:0285-7626

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  • ペリジニン,フコキサンチン類縁体合成と光合成を担うエネルギー準位の性質 Reviewed

    梶川敬之, 矢野恒記, 小澄大輔, 橋本秀樹, FRANK Harry, 坂口和彦, 木梨尚人, 品田哲郎, 勝村成雄

    日本化学会講演予稿集   94th ( 4 )   1482   2014.03( ISSN:0285-7626

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  • 高度に官能基化された単環性phlorglucinol類の全合成 Reviewed

    西村栄治, 大船泰史, 品田哲郎

    天然有機化合物討論会講演要旨集(Web)   56th   537‐542(J‐STAGE)   2014( ISSN:2433-1856

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  • セスクアテルペン環化酵素を基軸とするテルペン創出経路の開拓 Reviewed

    上田大次郎, 山鹿宏彰, 岡本渉, 遠塚悠輔, 品田哲郎, 星野力, 佐藤努

    天然有機化合物討論会講演要旨集(Web)   56th   103‐108(J‐STAGE)   2014( ISSN:2433-1856

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  • 高度にアルキル化されたフロログルシノール誘導体の合成研究 Reviewed

    西村栄治, 大船泰史, 品田哲郎

    香料・テルペンおよび精油化学に関する討論会講演要旨集   57th   61 - 63   2013.10

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  • セスクアテルペン環化酵素の部位特異的変異および非天然型テルペンの創出 Reviewed

    上田大次郎, 岡本渉, 山本彩乃, 遠塚悠輔, 品田哲郎, 仲野千秋, 佐藤努

    香料・テルペンおよび精油化学に関する討論会講演要旨集   57th   369 - 371   2013.10

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  • 長鎖イソプレノイドの合成研究 Reviewed

    遠塚悠輔, 品田哲郎

    香料・テルペンおよび精油化学に関する討論会講演要旨集   57th   64 - 66   2013.10

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  • ペリジニンおよびフコキサンチン類縁体の合成と光合成を担うエネルギー準位の性質 Reviewed

    矢野恒記, 梶川敬之, 奥村聡, 小澄大輔, 橋本秀樹, FRANK H. A., 坂口和彦, 品田哲郎, 勝村成雄

    香料・テルペンおよび精油化学に関する討論会講演要旨集   57th   339 - 341   2013.10

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  • アクロメリン酸Aの合成研究 Reviewed

    御前公美, 大船泰史, 品田哲郎

    複素環化学討論会講演要旨集   43rd   203 - 204   2013.10

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  • Bacillus clausii由来のE型プレニル鎖伸長酵素の機能同定による非環状テルペン生合成経路の解析 Reviewed

    山鹿宏彰, 遠塚悠輔, 品田哲郎, 仲野千秋, 佐藤努

    イソプレノイド研究会例会講演要旨集   23rd   12   2013.09

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  • キイロスズメバチの巣に含まれる生物活性分子 Reviewed

    品田哲郎, 大船泰史, 藤原由美子, 鈴木幸一

    トキシンシンポジウム予稿集   60th   110 - 113   2013.06( ISSN:1344-9346

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  • 高度にアルキル化されたphloroglucinol誘導体の合成研究 Reviewed

    西村栄治, 品田哲郎, 大船泰史

    日本化学会講演予稿集   93rd ( 4 )   1256   2013.03( ISSN:0285-7626

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  • 電子不足オレフィンとフラン誘導体を用いたシクロプロパン化反応 Reviewed

    松本遼太郎, 真鍋敦, 品田哲郎, 大船泰史

    日本化学会講演予稿集   93rd ( 4 )   1234   2013.03( ISSN:0285-7626

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  • クロスカップリング反応を利用した3位置換‐2‐ピリドン‐6‐カルボン酸の合成研究 Reviewed

    御前公美, 品田哲郎, 大船泰史

    日本化学会講演予稿集   93rd ( 4 )   1234   2013.03( ISSN:0285-7626

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  • β,β‐ジ置換α,β‐デヒドロアミノ酸エステルの立体選択的合成法の開発 Reviewed

    安川佳史, 保野陽子, 品田哲郎, 大船泰史

    日本化学会講演予稿集   93rd ( 4 )   1234   2013.03( ISSN:0285-7626

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  • 長鎖ポリイソプレノイドの立体制御合成 Reviewed

    村田悠輔, 品田哲郎, 大船泰史

    日本化学会講演予稿集   93rd ( 4 )   1257   2013.03( ISSN:0285-7626

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  • シクロプロパン環を導入したジアミノピメリン酸の合成研究 Reviewed

    若林由華, 島本啓子, 品田哲郎, 大船泰史

    日本化学会講演予稿集   93rd ( 4 )   1224   2013.03( ISSN:0285-7626

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  • 鎖状テルペン側鎖置換型JHSB3アナログの合成 Reviewed

    安藤祐美, 真鍋敦, 品田哲郎, 大船泰史

    日本化学会講演予稿集   93rd ( 4 )   1257   2013.03( ISSN:0285-7626

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  • 金触媒を用いた1‐アリール‐3‐ブチン‐1‐オール類の環化反応。置換ナフタレン類の合成。 Reviewed

    下田愛里, 岡田拓也, 品田哲郎, 坂口和彦, 大船泰史

    日本化学会講演予稿集   93rd ( 4 )   1344   2013.03( ISSN:0285-7626

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  • 固相合成によるα‐アミノスクアリン酸含有ペプチドの合成 Reviewed

    前田健太郎, 品田哲郎, 大船泰史

    日本化学会講演予稿集   93rd ( 4 )   1223   2013.03( ISSN:0285-7626

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  • ビスデヒドロアミノ酸の触媒的不斉水素化反応による光学活性モノアシルジアミノジカルボン酸の合成研究 Reviewed

    末内優輝, 品田哲郎, 大船泰史

    日本化学会講演予稿集   93rd ( 4 )   1224   2013.03( ISSN:0285-7626

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  • 三機能性セスタテルペン/トリテルペン/セスクアテルペン合成酵素の同定及び環状・非環状構造の決定に関与するアミノ酸残基の探索 Reviewed

    佐藤努, 小坂明彩香, 山本彩乃, 山鹿宏彰, 村田悠輔, 品田哲郎, 仲野千秋, 星野力

    日本農芸化学会大会講演要旨集(Web)   2013   2C22P07 (WEB ONLY)   2013.03( ISSN:2186-7976

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  • 有機合成化学を起点とする鎖状セスキテルペン型昆虫ホルモンの探索 Reviewed

    品田哲郎

    香料・テルペンおよび精油化学に関する討論会講演要旨集   56th   R.5-R.8   2012.10

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  • 鎖状テルペン側鎖置換型JHSB3アナログの合成 Reviewed

    安藤祐美, 御前公美, 村田悠輔, 真鍋敦, 品田哲郎, 大船泰史

    香料・テルペンおよび精油化学に関する討論会講演要旨集   56th   68 - 70   2012.10

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  • 金触媒環化反応による置換ナフタレンの合成 Reviewed

    下田愛里, 岡田拓也, 品田哲郎, 坂口和彦, 大船泰史

    香料・テルペンおよび精油化学に関する討論会講演要旨集   56th   110 - 112   2012.10

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  • 光学活性ピロリンの簡便な合成法の開発 Reviewed

    大江健太郎, 品田哲郎, 大船泰史

    複素環化学討論会講演要旨集   42nd   165 - 166   2012.09

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  • 置換ピリドンカルボン酸類の新規合成法の開発 Reviewed

    品田哲郎, 白井和光, 大船泰史

    複素環化学討論会講演要旨集   42nd   1 - 2   2012.09

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  • スクアリン酸含有アミノ酸を組み込んだ新規ペプチドアナログ合成 Reviewed

    前田健太郎, 木庭雄一, 石田捻和, 品田哲郎, 大船泰史

    天然有機化合物討論会講演要旨集(Web)   54th   387‐392(J‐STAGE)   2012.09( ISSN:2433-1856

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  • Structure determination of a natural juvenile hormone isolated from a heteropteran insect Reviewed

    Toyomi Kotaki, Tetsuro Shinada, Hideharu Numata

    Psyche   2012.03( ISSN:00332615

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    Juvenile hormone (JH), which occurs in several forms in different insects, is one of the most important insect hormones. The structure of JH in Heteroptera has not been elucidated until recently, although insects in this suborder have long been used as experimental animals for JH research. Here we review the structure determination of a novel JH in a stink bug, Plautia stali, which was named juvenile hormone III skipped bisepoxide [JHSB 3: methyl (2R,3S,10R)-2,3;10,11-bisepoxyfarnesoate], based on the arrangement of two epoxides at C2,3 and C10,11 with a skipped double bond at C6,7. Copyright © 2012 Toyomi Kotaki et al.

    DOI: 10.1155/2012/924256

  • カメムシ目昆虫におけるJHSB3の普遍性:陸生カメムシとセミでの検討 Reviewed

    小滝豊美, 品田哲郎, 貝原加奈子, 大船泰史, 沼田英治

    日本応用動物昆虫学会大会講演要旨   56th   142   2012.03

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  • チャバネアオカメムシ由来の幼若ホルモン,JHSB3の構造活性相関 Reviewed

    品田哲郎, 貝原加奈子, 大船泰史, 沼田英治, 小滝豊美

    日本応用動物昆虫学会大会講演要旨   56th   142   2012.03

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  • 3‐位置換‐2‐ピリドン‐6‐カルボン酸の新規合成 Reviewed

    白井和光, 品田哲郎, 大船泰史

    日本化学会講演予稿集   92nd ( 4 )   1180   2012.03( ISSN:0285-7626

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  • クマバチ由来の新規ペプチド類の構造と生物活性 Reviewed

    河上紘子, 品田哲郎, 大船泰史, 志賀向子, 後藤慎介

    日本化学会講演予稿集   92nd ( 4 )   1181   2012.03( ISSN:0285-7626

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  • キラルイソシアノ酢酸エステルを用いた光学活性アミノ酸類の合成研究 Reviewed

    山田銀司, 大江健太郎, 品田哲郎, 大船泰史

    日本化学会講演予稿集   92nd ( 4 )   1180   2012.03( ISSN:0285-7626

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  • α‐ジフェニルホスホノグリシネートを用いたE‐選択的デヒドロアミノ酸エステルの合成 Reviewed

    保野陽子, 山田健, 品田哲郎, 大船泰史

    日本化学会講演予稿集   92nd ( 4 )   1182   2012.03( ISSN:0285-7626

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  • 立体配座を固定した2,6‐ジアミノピメリン酸誘導体の合成研究 Reviewed

    若林由華, 末内優輝, 島本啓子, 品田哲郎, 大船泰史

    日本化学会講演予稿集   92nd ( 4 )   1181   2012.03( ISSN:0285-7626

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  • 金触媒を用いた1‐アリール‐3‐ブチン‐1‐オール類の環化反応.置換ナフタレンの合成 Reviewed

    下田愛里, 岡田拓也, 品田哲郎, 坂口和彦, 大船泰史

    日本化学会講演予稿集   92nd ( 4 )   1338   2012.03( ISSN:0285-7626

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  • 酸触媒を用いたα‐シロキシ‐α‐アルケニルシランの不斉転写型分子内環化反応 Reviewed

    池田直子, 赤木航, 東野勝人, 品田哲郎, 坂口和彦, 大船泰史

    日本化学会講演予稿集   92nd ( 4 )   1338   2012.03( ISSN:0285-7626

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  • 繰り返し連結によるα‐アミノスクアリン酸ペプチドの合成 Reviewed

    前田健太郎, 松本遼太郎, 品田哲郎, 大船泰史

    日本化学会講演予稿集   92nd ( 4 )   1180   2012.03( ISSN:0285-7626

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  • 繰り返しユニット連結反応を用いた鎖状テルペンアナログの合成 Reviewed

    安藤祐美, 真鍋敦, 品田哲郎, 大船泰史

    日本化学会講演予稿集   92nd ( 4 )   1165   2012.03( ISSN:0285-7626

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  • P-41 Synthesis of Novel Peptide Analogs by Incorporation of Squaric Acid Containing Amino Acid(Poster Presentation) Reviewed

    Maeda Kentaro, Kiniwa Yuuichi, Ishida Toshikazu, Shinada Tetsuro, Ohfune Yasufumi

    Symposium on the Chemistry of Natural Products Steering Committee, Symposium on the Chemistry of Natural Products, symposium papers   54 ( 0 )   387 - 392   2012

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    Recently, many α-amino acid analogs (AAA) in which the carboxyl group of α-amino acids is replaced with other acidic functional groups, e.g., sulfinic acid, sulfonic acid, phosphinic acid, phosphonic acid, boronic acid, and tetrazole, have been developed. Incorporation of these AAAs into biologically active peptides has received significant attention from bioorganic and medicinal chemists. We have recently developed α-amino squaric acid (-ASQ)bearing a 4-hydroxy-2,3-dioxocyclobut-1 -enyl (SQ) group as a carboxylic acid surrogate of amino acids. The SQ group is characterized by its planar structure, acidic OH group, and electron deficient property, and widely employed as a potent carboxylic acid surrogate in medicinal chemistry. These chemical properties prompted us to investigate the synthesis of new α-ASQ-containing peptides. We will report the synthesis of novel α-ASQ-containing peptides in liquid phase and the construction of the peptide library by solid phase synthesis. Conformational analysis and preliminary biological evaluation of these peptides will be discussed.

    CiNii Article

  • クマバチ毒嚢由来の生物活性ペプチド Reviewed

    品田哲郎, 河上紘子, 大船泰史, 志賀向子, 後藤慎介

    トキシンシンポジウム予稿集   59th   80 - 83   2012( ISSN:1344-9346

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  • 細胞増殖抑制活性の増大を目指した細胞膜透過型ヤママリンの合成 Reviewed

    大江高穂, 石黒慎一, 今井邦雄, 品田哲郎, 鈴木幸一

    東北蚕糸・昆虫利用研究報告   ( 35/36 )   20   2011.12( ISSN:1346-986X

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  • 繰り返しユニット連結法による鎖状テルペン類の立体選択的合成 Reviewed

    真鍋敦, 品田哲郎, 大船泰史

    香料・テルペンおよび精油化学に関する討論会講演要旨集   55th   75 - 77   2011.11

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  • α‐ヒドロキシシランを用いた分子内カチオン環化反応 Reviewed

    東野勝人, 赤木航, 池田直子, 品田哲郎, 坂口和彦, 大船泰史

    天然有機化合物討論会講演要旨集   53rd   655 - 660   2011.09

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  • カメムシ目昆虫由来の幼若ホルモンJHSB3の構造活性相関 Reviewed

    貝原加奈子, 品田哲郎, 大船泰史, 小滝豊美, 沼田英治

    天然有機化合物討論会講演要旨集   53rd   457 - 462   2011.09

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  • ハチ毒の多様性 Reviewed

    品田哲郎

    (公社)日本生化学会, 生化学   84回   ROMBUNNO.1S14A-2 - 2   2011.09( ISSN:0037-1017

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  • これからの天然物化学 天然神経毒アミノ酸類の全合成 Reviewed

    大船泰史, 品田哲郎

    化学工業   62 ( 8 )   642 - 648   2011.08( ISSN:0451-2014

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  • Total synthesis of neurotoxic amino acids from natural origin Reviewed

    大船 泰史, 品田 哲郎

    化学工業社, 化学工業   62 ( 8 )   642 - 648   2011.08( ISSN:04512014

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  • カメムシ目昆虫におけるJHSB3の普遍性:3種の陸生カメムシでの検討 Reviewed

    小滝豊美, 品田哲郎, 貝原加奈子, 大船泰史, 沼田英治

    日本応用動物昆虫学会大会講演要旨   55th   156   2011.03

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  • 新規幼若ホルモン,JHSB3の構造決定とカメムシ類におけるJH研究の今後 Reviewed

    小滝豊美, 品田哲郎

    日本応用動物昆虫学会大会講演要旨   55th   233   2011.03

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  • E‐選択的デヒドロアミノ酸エステル合成法の開発:添加剤の立体選択性に及ぼす効果 Reviewed

    保野陽子, 山田健, 品田哲郎, 大船泰史

    日本化学会講演予稿集   91st ( 4 )   1177   2011.03( ISSN:0285-7626

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  • カイトセファリン類縁体の合成と神経活性 Reviewed

    越智小央里, 品田哲郎, 大船泰史, 島本啓子

    日本化学会講演予稿集   91st ( 4 )   1177   2011.03( ISSN:0285-7626

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  • α‐ヒドロキシ‐α‐アルケニルシランを用いた立体選択的SN2’型光延反応 Reviewed

    池田直子, 東野勝人, 品田哲郎, 坂口和彦, 大船泰史

    日本化学会講演予稿集   91st ( 4 )   1268   2011.03( ISSN:0285-7626

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  • α‐アミノスクアリン酸含有ペプチドライブラリーの合成研究 Reviewed

    木庭雄一, 品田哲郎, 大船泰史

    日本化学会講演予稿集   91st ( 4 )   1176   2011.03( ISSN:0285-7626

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  • 新規Horner‐Wadsworth‐Emmons試薬の開発に基づくカロテノイド類の効率的合成 Reviewed

    山田健, 岡田惠次, 品田哲郎, 大船泰史, 橋本秀樹

    日本化学会講演予稿集   91st ( 4 )   1188   2011.03( ISSN:0285-7626

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  • 酸触媒によるα‐ヒドロキシ‐α‐アルケニルシランの不斉転写型分子内環化反応 Reviewed

    赤木航, 東野勝人, 品田哲郎, 坂口和彦, 大船泰史

    日本化学会講演予稿集   91st ( 4 )   1269   2011.03( ISSN:0285-7626

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  • 繰返しユニット連結反応による鎖状テルペン類の立体選択的合成 Reviewed

    真鍋敦, 貝原加奈子, 品田哲郎, 大船泰史

    日本化学会講演予稿集   91st ( 4 )   1188   2011.03( ISSN:0285-7626

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  • 独居性ハナバチ由来の新規ペプチド類の構造と生物活性 Reviewed

    河上紘子, 品田哲郎, 大船泰史, 志賀向子, 後藤慎介

    日本化学会講演予稿集   91st ( 4 )   1177   2011.03( ISSN:0285-7626

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  • ショウガ科植物Kaempferia parviflora根茎のキサンチンオキシダーゼ阻害作用 Reviewed

    村田和也, 出口貴浩, 伊藤仁久, 松田秀秋, 中尾紀久世, 新谷卓弘, 藤田貴則, 東野正行, 吉岡百合, 松村晋一, 田中里佳, 品田哲郎, 大船泰史

    (公社)日本薬学会, 日本薬学会年会要旨集   131st ( 2 )   217 - 217   2011.03( ISSN:0918-9823

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  • チャバネアオカメムシにおける幼若ホルモン(JHSB3)の構造決定と害虫管理への応用の可能性 Reviewed

    小滝豊美, 品田哲郎

    植物防疫   65 ( 2 )   126-130,71(3)   2011.02( ISSN:0037-4091

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  • JHSB3, a Novel Juvenile Hormone Determined in the Brown-Winged Green Bug, Plautia stali and its Possibilities to Develop Control Agents for the Pest Management Reviewed

    小滝 豊美, 品田 哲郎

    日本植物防疫協会, Plant protection   65 ( 2 )   126 - 130,図巻頭1p   2011.02( ISSN:00374091

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  • P-58 Cationic Intramolecular Cyclization Reaction of α-Hydroxysilanes(Poster Presentation) Reviewed

    Higashino Masato, Akagi Wataru, Ikeda Naoko, Shinada Tetsuro, Sakaguchi Kazuhiko, Ohfune Yasufumi

    Symposium on the Chemistry of Natural Products Steering Committee, Symposium on the Chemistry of Natural Products, symposium papers   53 ( 0 )   655 - 660   2011

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    The asymmetric cationic cyclization reaction is the key reaction in the biosynthesis of the natural products such as terpenoids and steroids, and recognized as one of the important research issues in synthetic organic chemistry. During the course of our recent studies regarding the reactions of an α-silyl cation, which is presumed to be a short-lived reactive species, we found that an acidic treatment of an α-alkenyl-α-hydroxysilane afforded the intramolecular Friedel-Crafts type cyclization product via a generation of the putative a-silyl cation. In this report, our recent efforts toward the chirality transferring Friedel-Crafts cyclization of an optically active α-alkenyl-α-hydroxysilane and its silyl ether are described. The treatment of the optically active α-alkenyl-α-hydroxysilane 11a with TMSOTf (1 equiv) underwent the cyclization reaction at the γ carbon attached to the silicon in a highly regioselective manner to give the vinylsilane-containing cyclized product 12. Despite the cationic reaction conditions, the chirality of the starting lla was significantly transferred to the product 12. The corresponding tent-butyl substituted analog 14 underwent the cyclization reaction to give the racemic product 15. These results indicated that the silyl group played a crucial role in the chirality transfer of the present cyclization. After several attempts, the use of a catalytic amount of TMSOTf or TfOH was found to be quite effective for the chirality transfer to produce the cyclized product 12 with a small loss of their starting optical purity. The catalytic reaction pathway of the present intramolecular Friedel-Crafts cyclization is underway.

    CiNii Article

  • P-63 Structure Activity Relationship Study of JHSB_3(Poster Presentation) Reviewed

    Kaihara Kanako, Shinada Tetsuro, Ohfune Yasufumi, Kotaki Toyomi, Numata Hideharu

    Symposium on the Chemistry of Natural Products Steering Committee, Symposium on the Chemistry of Natural Products, symposium papers   53 ( 0 )   457 - 462   2011

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    Juvenile hormone (JH) is an important insect hormone that maintains the immature characters during development (a juvenilizing effect). The structure determination studies have been extensively implemented due to the biological importance of JH in insect physiology. Moreover, JH has attracted much attention as a prime lead molecule to develop a "third-generation pesticide", because JH is a natural hormone and its mimics would be advantageous in terms of the suppression of a drug-resistance. In fact, many JH analogs have been developed based on the structures of JH I (1), JH II (2), and JH III (3). We have recently achieved the structure determination of a novel JH from a stink bug, Plautia stali and are named it juvenile hormone III skipped bisepoxide (JHSB3). This is the first example of the JH isolated from heteropteran insects. Heteroptera includes many agricultural and medical pests. In this study, we explored structure activity relationship of JHSB3 toward development of heteropteran specific insecticides. Various analogs were synthesized and subjected to the juvenilizing activity test using last instar nymphs of P. stali. These results indicated that the ester carbonyl group together with two epoxides at C2,3 and C10,11 were proven to be the crucial functional groups for the juvenilizing activity. Among the analogs, we found highly potent analogs in which the C7 position of JHSB3 was saturated (0.1 μg/insect). The methoxy analogs where the epoxide moiety at C10,11 was substituted with a methoxy group exerted moderate juvenilizing activities. These results would be useful information to develop heterpoteran specific insecticides.

    CiNii Article

  • カメムシ由来新規幼若ホルモンの類縁体合成と構造活性相関 Reviewed

    貝原加奈子, 品田哲郎, 大船泰史, 沼田英治, 小滝豊美

    香料・テルペンおよび精油化学に関する討論会講演要旨集   54th   283 - 285   2010.10

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  • C‐H結合活性化と中心金属の酸化を伴うコバルト(III)錯体の合成 Reviewed

    竹口勝也, 品田哲郎, 大船泰史, 桑村直人, 廣津昌和, 西岡孝訓, 橋本秀樹, 木下勇

    錯体化学討論会講演要旨集   60th   83   2010.09

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  • (-)‐カイニン酸の効率的全合成 Reviewed

    大江健太郎, 品田哲郎, 大船泰史

    有機合成化学セミナー講演予稿集   27th   110   2010.09

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  • カメムシ由来新規幼若ホルモンの類縁体合成と変態阻害活性評価 Reviewed

    貝原加奈子, 品田哲郎, 大船泰史, 沼田英治, 小滝豊美

    有機合成化学セミナー講演予稿集   27th   102   2010.09

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  • α‐ヒドロキシ‐α‐アルケニルシランを用いた立体選択的なSN2’型光延反応 Reviewed

    東野勝人, 池田直子, 品田哲郎, 坂口和彦, 大船泰史

    有機合成化学セミナー講演予稿集   27th   116   2010.09

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  • (-)‐カイニン酸の効率的全合成 Reviewed

    大江健太郎, 品田哲郎, 大船泰史

    天然有機化合物討論会講演要旨集   52nd   91 - 96   2010.09

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  • カメムシ類の新規幼若ホルモン(JHSB3)の同定 Reviewed

    小滝豊美, 品田哲郎, 貝原加奈子, 大船泰史, 沼田英治

    農業生物資源研究所主要な研究成果   2009   16 - 17   2010.05( ISSN:1347-4294

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  • 3‐デオキシカイトセファリンの合成研究 Reviewed

    越智小央里, 濱田まこと, 品田哲郎, 大船泰史

    日本化学会講演予稿集   90th ( 4 )   1076   2010.03( ISSN:0285-7626

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  • カイニン酸の効率的全合成 Reviewed

    大江健太郎, 品田哲郎, 大船泰史

    日本化学会講演予稿集   90th ( 4 )   1079   2010.03( ISSN:0285-7626

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  • カイトセファリン右側鎖部を有する新規グルタミン酸類縁体の合成研究 Reviewed

    保野陽子, 濱田まこと, 品田哲郎, 大船泰史

    日本化学会講演予稿集   90th ( 4 )   1076   2010.03( ISSN:0285-7626

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  • JHSB3のホルモンとしての生物学的機能の検証 Reviewed

    小滝豊美, 品田哲郎, 貝原加奈子, 大船泰史, 沼田英治

    日本応用動物昆虫学会大会講演要旨   54th   67   2010.03

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  • ジフェニルホスホノグリシン誘導体を用いるE‐選択的デヒドロアミノ酸エステルの合成 Reviewed

    濱田まこと, 品田哲郎, 大船泰史

    日本化学会講演予稿集   90th ( 4 )   1076   2010.03( ISSN:0285-7626

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  • 新規幼若ホルモン(JHSB3)類縁体の合成と活性 Reviewed

    貝原加奈子, 品田哲郎, 大船泰史, 沼田英治, 小滝豊美

    日本化学会講演予稿集   90th ( 4 )   1072   2010.03( ISSN:0285-7626

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  • 固相合成を指向したα‐アミノスクアリン酸含有ペプチドの合成研究 Reviewed

    木庭雄一, 品田哲郎, 大船泰史

    日本化学会講演予稿集   90th ( 4 )   1078   2010.03( ISSN:0285-7626

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  • Efficient Total Synthesis of (-)-Kainic Acid Reviewed

    Oe Kentaro, Shinada Tetsuro, Ohfune Yasufumi

    Symposium on the Chemistry of Natural Products Steering Committee, Symposium on the Chemistry of Natural Products, symposium papers   52 ( 0 )   91 - 96   2010

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    Kainic acid, isolated from the marine alga Digenea simplex by Takemoto et al. in 1953, was a parent memter of kainoids family of natural products that display potent anthelmintic properties and neuroexcitatory activities in the mammalian central nervous system. Kainic acid has attracted much attention as a synthetic target due to the above mentioned biological activity as well as the unique structural feature possessing three contiguous chiral centers on the pyrrolidine ring. More than thirty total syntheses including three large scale syntheses have been reported. In this report, we describe an efficient total synthesis of kainic acid which is highlighted by stereoselective construction of the trans-pyrroline via the copper-catalyzed Michael additon-cyclization reacton of chiral isocyanoacetamide 2 with α,β-unsaturated ketone 3. Treatment of isocyanoacetamide 2 with α,β-unsaturated ketone 3 in the presence of bis(N-tert-butylsalycylideneiminato)copper afforded pyrroline 4 in a single operation as a sole diasteromer in 54% yield. Removal of the chiral auxiliary followed by protection of the enamine nitrogen with a Boc group gave ester 8. The conversion to protected kainic acid methyl ketone 13 was achieved in a highly diastereoselective manner (dr=25:1) by the following sequence of transformations; (1) hydrolysis of the methyl ester to carboxylic acid 11, (2) reduction using excess L-Selectride, (3) treatment with aqueous HCl, and (4) esterification with CH_2N_2. The total synthesis of (-)-kainic acid from 13 was accomplished by the chemoselective olefination of the ketone, hydrolysis of the methyl ester, and removal of the N-Boc and t-Bu ester groups under acidic condition. The synthesis involved of 9 steps sequence (16.8% overall yield) of reaction from 2.

    CiNii Article

  • カイトセファリンの構造活性相関研究 Reviewed

    品田哲郎, 濱田まこと, 森正広, 大船泰史, 島本啓子

    メディシナルケミストリーシンポジウム講演要旨集   28th   368 - 369   2009.11( ISSN:0919-214X

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  • 独居性カリウドバチが昆虫を麻痺させる現象はどこまでわかってきたのか? : 最新機器・分析法でファーブル『昆虫記』の謎に迫る Reviewed

    品田 哲郎

    公益社団法人 日本農芸化学会 化学と生物   47 ( 9 )   594 - 596   2009.09( ISSN:0453073X

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  • Asymmetric synthesis of α-substituted α-amino acids: Strecker and claisen approaches Reviewed

    Yasufumi Ohfune, Kazuhiko Sakaguchi, Tetsuro Shinada

    ACS Symposium Series   1009   57 - 71   2009.06( ISSN:00976156

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    Two efficient methods for the synthesis of a class of optically active α-substituted α-amino acids developed in our laboratories are disclosed. An asymmetric version of the Strecker synthesis of α-acyloxy ketones possessing an optically acitive amino acid as a chirality transferring acyl group produced acyclic and cyclic α-substituted serine analogs. Novel vinylsilane-containing α- or α,β-substituted α- amino acids were synthesized by the Claisen rearrangement of α-acyloxy-α- alkenylsilanes. These methods were used for the synthesis of biologically active amino acids and natural products. © 2009 American Chemical Society.

    DOI: 10.1021/bk-2009-1009.ch004

  • 昆虫が利用する生物間攻防分子--その機能と役割 (特集 生物毒--新たな切り口でみる生物間の攻防) -- (海洋毒,キノコ毒,昆虫毒) Reviewed

    品田 哲郎

    エヌ・ティー・エス 遺伝   63 ( 2 )   70 - 73   2009.03( ISSN:03870022

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    CiNii Article

  • 【生物毒 新たな切り口でみる生物間の攻防】 海洋毒、キノコ毒、昆虫毒 昆虫が利用する生物間攻防分子 その機能と役割 Reviewed

    品田 哲郎

    (株)エヌ・ティー・エス, 遺伝: 生物の科学   63 ( 2 )   70 - 73   2009.03( ISSN:0387-0022

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  • Asymmetric Synthesis and Application of α-Amino Acids. Asymmetric synthesis of α-substituted α-amino acids: Strecker and Claisen approaches

    ACS book symposia series, ed by Soloshonok, V. A.; Izawa, K.   1009   57^-71   2009

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  • 昆虫由来の生物間攻防分子、その機能と意味

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    生物の科学・遺伝   63   70 - 73   2009

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  • 独居性カリウドバチが昆虫を麻痺させる現象はどこまでわかってきたのか?

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    化学と生物   47   594 - 596   2009

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  • 生理活性物質合成を指向したα-置換アミノ酸類の不斉合成

    37   22 - 32   2009

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  • Efficient Total Synthesis of Kaitocephalin and its Structure-activity Relationship Study Reviewed

    Shinada Tetsuro, Hamada Makoto, Mori Masahiro, Ohfune Yasufumi, Shimamoto Keiko

    Division of Organic Chemistry, The Pharmaceutical Society of Japan, Proceedings of the Symposium on Progress in Organic Reactions and Syntheses   35 ( 0 )   28 - 28   2009

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    Kaitocephalin was isolated from a filamentous fungus Eupenicillium shearii PF1191 by Seto and Shin-ya et al. by the screening for novel AMPA/KA antagonist employing chick telencephatic neurons. Kaitocephalin suppressed kainate excitotoxicity in this assay (EC50 = 0.68 M) and exhibited lower cytotoxicity against these neurons (>500 M). Therefore, kaitocephalin has been promising to be a potent lead compound for development of therapeutic agents toward various ischemia-reperfusion injuries such as stroke and epilepsy. Three groups including our group have succeeded in the total synthesis. However, it still required a practical synthetic approach that enables to supply sufficient amounts of natural product and its structurally related analogs for the neurobiological assays. We describe the highly efficient total synthesis of kaitocephalin and its analogs based on the diastereoselective coupling of A, B, and C, and their structure-activity relationship study.

    CiNii Article

  • Efficient Total Synthesis of Kaitocephalin and Neurobiological Evaluation of Its Analogs Reviewed

    Hamada Makoto, Mori Masahiro, Shinada Tetsuro, Ohfune Yasufumi, Shimamoto Keiko

    Symposium on the Chemistry of Natural Products Steering Committee, Symposium on the Chemistry of Natural Products, symposium papers   51 ( 0 )   401 - 406   2009

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    (-)-Kaitocephalin (1), isolated from a filamentous fungus Eupenicillium shearii PF1191 by Seto and Shin-ya et al., has attracted much attention due to its potent antagonist activity to ionotropic glutamate receptors. The structure of 1 is characterized by its 2,2,4-trisubstituted pyrroridine core assembled by N-acylalanine and threonine moieties connected with a carbon-carbon bond. In this presentation, we describe the efficient total synthesis of 1 from the known pyrroridine 8 in 12 steps. Neurobiological evaluation of its diastereomers, enantiomer, and functional froup removed analogs are also disclosed. The key to the total synthesis relied on the stereoselective construction of the five stereocenters including three chiral α-amino acid moieties. The three contiguous stereocenters of the right side chain were stereoselectively constructed by the aldol reaction of 6 with the known serinal ortho ester 7 and subsequent inversion of the C3 stereocenter of the resulting (3R)-9 to (3S)-11 via mild oxidation and reduction conditions. Conversion of the ortho ester to the methyl ester followed by the oxidation of the siloxymethyl side chain to the aldehyde gave 4. The alanine moiety was installed by Horner-Wadsworth-Emmons(HWE) olefination and stereoselective hydrogenation reactions. The use of the E-isomer of 3 was essential for the stereoselective preparation of the (9S)-14. To this end, E-selective dehydroamino acid synthesis using HWE reagent 5b was developed. All the protecting groups of (9S)-14 were removed at once by using AlCl_3-Me_2S to give kaitocephalin (1). Each step (12 steps) was reproducible and carried out in a gram quantity. Thus, stereoselective and short synthetic route to (-)-kaitocephalin 1 was established. Radio ligand binding assay of 1 and its analogs to iGluRs using rat brain synaptic membrane suggested that the C3 hydroxyl and C9 carboxyl groups are important for binding. In addition, the acyl amide moiet may be involved in the poteng binding. It is interesting to note that the enantiomer of 1 (ent-1) was a selective ligand of the NMDARs. Further biological evaluation is currently under investigation.

    CiNii Article

  • Asymmetric synthesis of α, α-disubstituted α-amino acids focusing on biologically active compounds Reviewed

    大船 泰史, 坂口 和彦, 品田 哲郎

    シーエムシー出版, Fine chemicals   37 ( 3 )   22 - 32   2008.03( ISSN:09136150

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  • 5 Structure Determination of a Novel Juvenile Hormone from Plautia crossota stali(Oral Presentation) Reviewed

    Shinada Tetsuro, Kaihara Kanako, Ohfune Yasufumi, Numata Hideharu, Kotaki Toyomi

    Symposium on the Chemistry of Natural Products Steering Committee, Symposium on the Chemistry of Natural Products, symposium papers   50 ( 0 )   53 - 58   2008

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    The juvenile hormone (JH) is one of the key insect hormones. Here we describe the novel structure of the heteropteran JH, named JHSB_3. We hypothesized four candidate structures 1-4 as a result of the following experimental results: 1) The in vitro product of the corpus allatum (CA) of a stink bug, Plautia crossota stali, analyzed by gas chromatography/chemical ionization-mass spectrometry (GC/MS) showed a molecular mass ion peak at m/z 300 [M+NH_4]^+, 2) The high resolution fast atom bombardment mass spectrometry of the same sample gave the exact mass ion peak [M+H]^+ of 283.1885 suggesting a molecular formula, C_<16>H_<27>O_4, identical to that of JHB_3, 3) Enhanced JH production by CA in vitro by the addition of excess E, E-farnesol to the medium, indicated an E,E-farnesol skeleton for the heteropteran JH. The four candidates were stereoselectively synthesized in an enantiomeric pure form via Katsuki-Sharpless epoxidation and Sharpless dihydroxylation reactions. The juvenilizing effect of the bisepoxides 1-4 on metamorphosis of the bug showed that 1 and 2 were more potent than 3 and 4. When the CA product was subjected to a chiral GC/MS, the CA product and 2 had the same retention time. Thus, the structure of the native JH in P.c. stali was determined as 2.

    CiNii Article

  • 生命科学研究におけるスクアリン酸の活用とその進歩 Reviewed

    品田 哲郎, 石田 稔和, 大船 泰史

    有機合成化学協会 有機合成化学協会誌   65 ( 1 )   32 - 45   2007.01( ISSN:00379980

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  • 生命科学研究におけるスクアリン酸の利用とその進歩

    品田哲郎、石田稔和、大船泰史

    有機合成化学協会誌   65 ( 1 )   30 - 43   2007

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  • 十字路 Reviewed

    西長 亨, 品田 哲郎, 松尾 豊

    社団法人 有機合成化学協会 有機合成化学協会誌   65 ( 1 )   67 - 67   2007

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  • 21 Total Synthesis of Marine Alkaloid, Amathaspiramide F Reviewed

    Sakaguchi Kazuhiko, Ayabe Miki, Watanabe Yusuke, Kawamura Kazushige, Okada Takuya, Shinada Tetsuro, Ohfune Yasufumi

    Symposium on the Chemistry of Natural Products Steering Committee, Symposium on the Chemistry of Natural Products, symposium papers   49 ( 0 )   121 - 126   2007

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    Amathaspiramides A-F are a class of marine alkaloids isolated from a New Zealand collection of the bryozoan Amathia wilsoni. Since these alkaloids were available in a minute quantities from the bryozoan, only preliminary pharmacological evaluation of these alkaloids has been reported, i.e., amathaspiramide E exhibited a potent antiviral activity and both A and E showed moderate antifungal and cytotoxic activities. The structures of amathaspiramides are characterized by their unique spirobicyclic framework containing three contiguous chiral centers and a dibrominated aromatic ring. We have been reported that the enolate-Claisen rearrangement of an α-acyloxy-α-alkenylsilane gave the rearranged product with a complete transfer of the original chirality. Based on these results, we planned the total synthesis of amathaspiramide F (1) using the enolate-Claisen rearrangement of the α-acyloxy-α-alkenylsilane with a Z-olefin geometry 4 (route A) or 5 (route B) as the key step: the reaction would produce 8 or 9 possessing the requisite chiral centers at CS and C9 (erythro relationship) together with a vinylsilane group convertible to the hemiaminal moiety of 1. The enolate-Claisen rearrangement of 4 (route A) having a proline as the acyloxy group was found to give undesired threo isomer 8 as the major product. On the other hand, the acyclic route (route B) underwent stereoselective rearrangement to give desired erythro isomer 9 (threo/erythro = 1: 7). The rearranged product 9 was converted to the spirobicyclic hemiaminal 12 via the pyrrolidine 10. The completion of the total synthesis of 1 was accomplished by the following sequence of reactions: (1) dibromination of the phenol group with n-Bu_4NBrCl_2 (2) methylation of the phenol with MeI, and (3) removal of the TFA group with LiBH_4.

    CiNii Article

  • P-48 Synthesis and Structure Revision of Manzacidin B Reviewed

    Shinada Tetsuro, Ikebe Eijiro, Oe Kentaro, Ohfune Yasufumi

    Symposium on the Chemistry of Natural Products Steering Committee, Symposium on the Chemistry of Natural Products, symposium papers   48 ( 0 )   589 - 594   2006

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    Manzacidin A-C, isolated from an Okinawan sponge Hymeniacidon sp., possess a unique structure consisting of an ester-linked bromopyrrolecarboxylic acid and a 3,4,5,6-tetrahydropyrimidine in which one of the amino groups attached to the C6 quarternary carbon center. The structures of manzacidin A (1) and C (3) have been confirmed as the C6 isomers with the same 4S configuration by our previous total synthesis of both 1 and 3. On the other hand, 4S,5S,6S configuration was assigned to the structure of manzacidin B (2) that was needed for the structural confirmation by the synthesis. We planned the syntheses of four possible diastereomers 4a-4d by stereochemically unambiguous processes starting with α-methyl Garner aldehyde (R)-5. The isomers, (4R,5S,6R)-4a and (4S,5R,6R)-4b, were synthesized from (E)-unsaturated ester 6a by the following sequence of transformations: (1) stereoselective dihydroxylation, (2) thionocarbonate formation followed by S_N2 azidation, and (3) reduction of the azide group, deprotection, amidination, and esterification with 4-bromopyrrolecarboxylate. Cu-catalyzed condensation of an isonitrile with (R)-5 was the key step for the synthesis of 4c,d. The reaction gave a 7: 1 mixture of trans-oxazolines 16a,b. Hydrolysis followed amidination-esterification gave a mixture of (4R,5R,6R)-4c (ent-2: major isomer) and (4S,5S,6R)-4d. Since the major isomer 4c, upon treatment with NaH, was isomerized to 4b, structures of 4c,d were assigned as above. Comparisons of the ^1H and ^<13>C NMR spectral data and sign of the optical rotation of 4a-d with those of natural product clearly indicated that (4S,5S,6R)-4d is identical in all respects with natural manzacidin B. Thus, the structure of manzacidin B was revised to 4d.

    CiNii Article

  • Stereoselective Synthesis of 2,5-Di- and 2,2,5-Trisubstituted Pyrrolidines by Allylation Reaction of Acyliminium Ion Reviewed

    Shinada Tetsuro, Hamada Makoto, Kawasaki Masanori

    Japan Institute of Heterocyclic Chemistry, Heterocycles   66 ( 0 )   511 - 525   2005.12( ISSN:03855414

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  • Asymmetric synthesis of α,α-disubstituted amino acids

    Europian Journal of Organic Chemistry   in press   2005

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  • Synthesis of Novel Squaryl Group Containing Amino Acids and Its Incorporation into Biologically Active Peptides Reviewed

    Shinada Tetsuro, Ishida Toshikazu, Ohfune Yasufumi

    Division of Organic Chemistry, The Pharmaceutical Society of Japan, Proceedings of the Symposium on Progress in Organic Reactions and Syntheses   31 ( 0 )   238 - 238   2005

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    We wish to report the synthesis of novel &alpha;-amino squaric acid analogs (&alpha;-ASqA) and their incorporation into Leu-Enkephalin. Two synthetic methods using a dianion enolates (method A) or an aminomalonate equivalent (method B) were developed to this objective. Method A involves an efficient generation of a dianion enolate from an N-Boc amino acid tert-butyl ester and its condensation with squaric acid diisopropyl ester. The resulting coupling products were transformed to the corresponding &alpha;-ASqAs by decarboxylation reaction. Alternatively, a sq-group containing amino malonate equivalent was used for the key carbon-carbon bond forming reaction to access to &alpha;-ASqAs (method B). The synthetic &alpha;-ASqA was incorporated into Gly2 of Leu-enkephalin.

    CiNii Article

  • 14 Total Synthesis of 5,6,11-Trideoxytetrodotoxin Reviewed

    Umezawa Taiki, Shinada Tetsuro, Ohfune Yasufumi

    Symposium on the Chemistry of Natural Products Steering Committee, Symposium on the Chemistry of Natural Products, symposium papers   47 ( 0 )   77 - 82   2005

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    Tetrodotoxin (TTX) is a toxic principle of puffer fish poisoning. TTX is a useful biological tool because of its specificity for blocking voltage-dependent sodium channels. 5,6,11-Trideoxy TTX (1), one of the congeners of TTX, has also been isolated from ovaries of puffers, Fugu poecilonotus, by Yasumoto et al. in 1995 and received significant interests in view of biosynthetic relationship with TTX. Synthetic studies of TTX and its congeners have been extensive due to their biological activities as well as their molecular complexity consisting of a quaternary carbon center attached to an amino group, concomitant polyol system, a cyclic guanidine containing an aminal, and an ortho acid for TTX or a δ-lactone for some of the congeners. In this report, we wish to describe the first total synthesis of 5,6,11-trideoxy TTX (1) and its 4-epimer 2. The synthesis was commenced with the known triol 7, prepared from (-)-quinic acid in 4 steps, which was converted to Strecker precursor 6 in 6 steps. 6 was subjected to an asymmetric transferring Strecker synthesis for the diastereoselective construction of a quaternary carbon center involving an amino group at C8a. Installation of a hydroxy group to C7 was accomplished by the Mislow-Evans rearrangement to give 20. Initial hydrogenation of 20 for the introduction of β-methyl group at C6 and subsequent pyrrolidine ring opening via lactam 24 gave alcohol 25. The hydroxyethyl group of 25 was transformed to a vinyl group in 3 steps to give 26. Inversion of the hydroxy group at C7 was performed by oxidation to a diketone followed by diastereoselective reduction to give cis-diol 4, This was converted to aldehyde 28, which, upon treatment with TMSCN in the presence of Et_3N, gave a cyanohydrin as an inseparable mixture of diastereomers. The mixture was guanidylated to give 29. Ozonolysis of the desired (9S)-29 followed by exposure to 20% TFA afforded a mixture of 5,6,11-trideoxyTTX (1), and its 4-epimer 2 and anhydro derivative 31. Thus, the total syntheses of 1 and 2 were accomplished.

    CiNii Article

  • 第5版実験化学講座、第16巻、アミノ酸、ペプチド、アミノ酸の不斉合成

    大船泰史、坂口和彦、品田哲郎、他

    日本化学会編、丸善   196 - 218   2005

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  • 2章 アミノ酸・ペプチド Reviewed

    大船泰史, 坂口和彦, 品田哲郎

    日本化学会編、第5版実験化学講座、有機化合物の合成(IV)   2005

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  • ヘテロ環状立体制御に基づくα&#8212;置換アミノ酸類の不斉合成

    大船泰史、品田哲郎

    化学工業社   55   50 - 57   2004

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  • MS/MSによるペプチドの一次構造解析を簡便にする方法:スクアリン酸をCRF誘導基に用いたペプチドのMS/MS解析

    Shinada, T., Ohfune, Y.

    化学と生物   41   99 - 101   2003

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  • Asymmetric Synthesis of a,a-Disubstituted a-Amino Acids

    My Favorite Organic Synthesis, Ed. by J. Syn. Org. Chem. Jpn.,   156 - 157   2002

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  • A Multi-functionalized Group: Squaric Acid

    55 ( 7 )   66 - 67   2000

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  • シアノクプレートの構造CuCN+2RLi = Higher Order Cuprates ?

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    化学と工業   50 ( 12 )   1784   1997

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Presentations

  • 新規イソクマリン合成法を用いた二量体天然物bipenicilisorinの全合成 Domestic conference

    中山淳, 福田瑛吾, 藤原維吹, 濱本健一郎, 品田哲郎

    日本薬学会 第143年会  2023.03  日本薬学会

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    Venue:札幌  

  • ロジウム触媒を用いる9-ベンゾイルカルバゾール類と内部アルキンの環化カップリングによるインデノン誘導体合成 Domestic conference

    落合紫帆、臼杵克之助、姜法雄、品田哲郎、佐藤 哲也

    日本化学会 第101回春季年会(2021)  2021.03 

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  • (2S,6R)-ジアミノ-(5R,7)-ジヒドロキシヘプタン酸(DADH)及びその誘導体の立体選択的合成 Domestic conference

    岡村 仁則、保野 陽子、滝川 浩郷、品田 哲郎

    日本農芸化学会 2021年度大会  2021.03 

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  • オケビラゴケ由来ビベンジルカンナビノイドの生合成研究 Domestic conference

    田浦 太志、高橋 宏暢、兼目 裕充、浅川 義範、保野 陽子、品田 哲郎

    日本農芸化学会 2021年度大会  2021.03 

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  • 非タンパク質構成アミノ酸DADH及びその誘導体の合成 Domestic conference

    岡村仁則、保野陽子、滝川浩郷、品田哲郎

    日本化学会 第101回春季年会(2021)  2021.03 

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  • クラスIBテルペン合成酵素の環状構造形成機構の解析 Domestic conference

    浅田和也、上田大次郎、三木邦夫、藤橋雅宏、品田哲郎、佐藤努

    日本農芸化学会 2021年度大会  2021.03 

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  • アルデヒドの簡便な重水素化法の開発と重水素化鎖状テルペン合成への応用 Domestic conference

    品田哲郎、保野陽子、岡村仁則、中山淳、熊懐克志、橘和航平、小澤圭太、田村優作、山本悠生

    日本化学会 第101回春季年会(2021)  2021.03 

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  • スクアレン合成酵素に似た放線菌由来芳香族プレニル基転移酵素の構造学的研究 Domestic conference

    永田 隆平、末宗 周憲、山本 将輝、小林 正弥、品田 哲郎、西山 真、永野 真吾、葛山 智久

    日本農芸化学会 2021年度大会  2021.03 

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  • アーキア型メバロン酸経路の鍵酵素ホスホ-trans-アンヒドロメバロン酸デカルボキシラーゼの酵素学的研究 Domestic conference

    松島夏海、栗木莉子、保野陽子、品田哲郎、吉村徹、邊見久

    日本農芸化学会 2021年度大会  2021.03 

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  • 好熱菌アーキア由来ホスホメバロン酸デヒドラターゼの活性中心に存在する鉄硫黄クラスターの解析 Domestic conference

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    日本農芸化学会 2021年度大会  2021.03 

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  • 好熱菌アーキア由来ホスホメバロン酸デヒドラターゼの活性中心に存在する鉄硫黄クラスターの解析 Domestic conference

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    日本農芸化学会 2021年度大会  2021.03 

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  • アーキア型メバロン酸経路の鍵酵素ホスホ-trans-アンヒドロメバロン酸デカルボキシラーゼの酵素学的研究 Domestic conference

    松島夏海, 栗木莉子, 保野陽子, 品田哲郎, 吉村徹, 邊見久

    日本農芸化学会 2021年度大会  2021.03 

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  • 有機合成化学を基盤とするテルペン系天然物の生合成および生物機能の解明 Invited Domestic conference

    品田哲郎

    有機合成化学協会 2019年度企業冠賞受賞講演会  2021.01 

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  • 有機合成化学を基盤とするテルペン系天然物の生合成および生物機能の解明 Invited Domestic conference

    品田哲郎

    有機合成化学協会 2019年度企業冠賞受賞講演会  2021.01 

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  • 含アジリジン天然物の推定生合成中間体の合成研究 Domestic conference

    岡村仁則、滝川浩郷、品田哲郎

    第64回香料・テルペンおよび精油化学に関する討論会( TEAC )  2020.10 

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  • クラスIBテルペン合成酵素の諸性質解析 マイナー生成物の同定および環化に重要な残基の特定 Domestic conference

    R. Stepanova, 菅原啓、上田大二郎、稲木隼人、三木邦夫、藤橋雅宏、保野陽子、品田哲郎、佐藤努

    第64回香料・テルペンおよび精油化学に関する討論会( TEAC )  2020.10 

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  • 納豆菌由来シンキセスクアテルペン類の酵素合成による同定 Domestic conference

    今井僚、小川佳央、高橋宏忠、品田哲郎、佐藤努,

    第64回香料・テルペンおよび精油化学に関する討論会( TEAC )  2020.10 

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  • 納豆菌由来シンキセスクアテルペン類の酵素合成による同定 Domestic conference

    今井僚, 小川佳央, 高橋宏忠, 品田哲郎, 佐藤努

    第64回香料・テルペンおよび精油化学に関する討論会( TEAC )  2020.10 

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  • 含アジリジン天然物の推定生合成中間体の合成研究 Domestic conference

    岡村仁則, 滝川浩郷, 品田哲郎

    第64回香料・テルペンおよび精油化学に関する討論会( TEAC )  2020.10 

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  • 非天然型オノセロイドの酵素合成 Domestic conference

    平井奈実、井上真緒、上田大二郎、品田哲郎、佐藤努

    第64回香料・テルペンおよび精油化学に関する討論会( TEAC )  2020.10 

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  • アンヒドロメバロン酸骨格を有するテルペン類の全合成 Domestic conference

    橘和航平、斎藤甲斐、岡村仁則、保野陽子、品田哲郎

    第64回香料・テルペンおよび精油化学に関する討論会( TEAC )  2020.10 

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  • 重水素化アルデヒド類の合成研究 Domestic conference

    熊懐克志、橘和航平、小澤圭太、田村優作、山本悠生、岡村仁則、保野陽子、品田哲郎

    第64回香料・テルペンおよび精油化学に関する討論会( TEAC )  2020.10 

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  • N-アシルカルバゾールを用いた選択的アミド化反応の開発 Domestic conference

    姜法雄 、保野陽子 、岡村仁則 、酒井明日実 、佐藤哲也 、久世雅樹 、品田哲郎

    第62回天然有機化合物討論会  2020.09 

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  • カンファー誘導体を備えたイソニトリルのアルドール反応に よるβ-ヒドロキシフェニルアラニン誘導体の合成研究(2): ウスチロキシンD の全合成研究 Domestic conference

    保野陽子、福和真、品田哲郎

    第63 回香料・テルペンおよび精油化学に関する討論会  2019.09 

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  • カンファー誘導体を備えたイソニトリルのアルドール反応に よるβ-ヒドロキシフェニルアラニン誘導体の合成研究(1) Domestic conference

    福和真・保野陽子・品田哲郎

    第63 回香料・テルペンおよび精油化学に関する討論会  2019.09 

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  • Bacillus 属細菌の新規テルペノイド生合成経路の解析 Domestic conference

    上田大次郎、藤橋雅宏 、松ヶ根沙織 、岡本渉 、西智之 、村上瑞気 、三木邦夫 、保野陽子、品田哲郎、橋本昌征 、佐藤努

    第61回天然有機化合物討論会  2019.09 

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  • N -ベンゾイルジアミノスベリン酸骨格を有する xCT 阻害剤の開発 Domestic conference

    保野陽子、水谷衣穂、末内優輝、若林由華、安尾望、島本啓子、品田哲郎

    第61回天然有機化合物討論会  2019.09 

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  • Synthetic Study of Phomopsin A : Catalytic Asymmetric Synthesis of β-OH-DOPA Domestic conference

    Kohei Yasuda, Yoko Yasuno, Tetsuro Shinada

    27th International Sciety of Heterocyclic Chemistry Congress  2019.09 

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  • First Total Synthesis of Antrimycin A and D Domestic conference

    Yoko Yasuno, Akito Nishimura, Akira Sawai, Ai Sekihara, Tetsuro Shinada

    27th International Sciety of Heterocyclic Chemistry Congress  2019.09 

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  • Synthesis of Polyfunctional Carotenoid by Cross-Coupling Strategy Domestic conference

    K. Sakaguchi, Y. Nishioka, N. Kinashi, T. Shinada, T. Nishimura, H. Hashimoto, S. Katsumura

    The 20th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 20)  2019.06 

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  • Stereochemistry of the β-Arginine Unit of SF-2132 Domestic conference

    Ai Sekihara, Yoko Yasuno, Tetsuro Shinada

    日本化学会 第99回春季年会(2019)  2019.03  日本化学会

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    Venue:兵庫県神戸市、甲南大学岡本キャンパス  

  • Synthetic Study of Ustiloxin D by Using Isonitrile Aldol Reaction Domestic conference

    Kazuma Fuku, Yoko Yasuno, Tetsuro Shinada

    日本化学会 第99回春季年会(2019)  2019.03  日本化学会

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    Venue:兵庫県神戸市、甲南大学岡本キャンパス  

  • Synthetic Study of Phomopsin A: Catalytic Asymmetric Synthesis of the Amino Acid Unit Domestic conference

    Kohei Yasuda, Yoko Yasuno, Tetsuro Shinada

    日本化学会 第99回春季年会(2019)  2019.03  日本化学会

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    Venue:兵庫県神戸市、甲南大学岡本キャンパス  

  • 微生物が生産する天然物のケミカルバイオロジー Invited Domestic conference

    品田哲郎

    BioMediacalForum 2019  2019.02  大阪府立大学理学研究科

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    Presentation type:Oral presentation (invited, special)  

    Venue:大阪府堺市、大阪府立大学学術交流会館  

  • シクロファン構造を有する天然有機化合物の合成と生物有機化学的展開 Invited Domestic conference

    品田哲郎

    岡山大学理学部化学科セミナー  2018.12  岡山大学理学部化学科

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    Presentation type:Oral presentation (invited, special)  

    Venue:岡山県岡山市、岡山大学  

  • オオケビラゴケが生産するビベンジルカンナビノイドの生合成研究 Domestic conference

    中川竜 一、黒崎文也、田浦太志、保野陽子、品田哲郎

    日本薬学会北陸支部第130回例会  2018.11  日本薬学会北陸支部

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    Venue:富山県富山市、富山大学杉谷キャンパス  

  • Catalytic Asymmetric Synthesis of Orthogonally Protected N-Acyl 2,7-Diaminosuberic Acid International conference

    Yoko Yasuno, Iho Mizutani, Yuki Sueuchi, Yuuka Wakabayashi, Nozomi Yasuo, Keiko Shimamoto, Tetsuro Shinada

    The 13th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)   2018.11  IKCOC-13

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    Venue:Rihga Royal Hotel, KYOTO, JAPAN,  

  • Polyfunctional Carotenoid Synthesis via Cross-Coupling Strategy International conference

    Kazuhiko Sakaguchi, Yuto Nishioka, Naoto Kinashi, Tetsuro Shinada, Takahiro Nishimura, Hideki Hashimoto, Shigeo Katsumura

    The 13th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)  2018.11  IKCOC-13

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    Venue:Rihga Royal Hotel, KYOTO, JAPAN  

  • Total Synthesis of SF-2132 International conference

    Ai Sekihara, Akira Sawai, Yoko Yasuno, Tetsuro Shinada

    The 13th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)   2018.11  IKCOC-13

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    Venue:Rihga Royal Hotel, KYOTO, JAPAN  

  • 新規ファミリーに属するテルペン合成酵素の基質認識部位の同定 Domestic conference

    稲木隼人, 佐藤努, 保野陽子, 品田哲郎, 三木邦夫, 藤橋雅宏

    日本結晶学会年会2018  2018.11  日本結晶学会

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    Venue:東京工業大学大岡山キャンパス  

  • One-pot Synthesis of Anthraquinones by Sc(OTf)3-catalyzed Tandem Reaction International conference

    Yoko Yasuno, Yohei Toriyama, Ryota Ogura, Tetsuro Shinada

    The 13th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)  2018.11  IKCOC-13

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    Presentation type:Poster presentation  

    Venue:Rihga Royal Hotel, KYOTO, JAPAN  

  • Total Synthesis of Ustiloxin D International conference

    Kazuma Fuku, Kohei Yasuda, Yoko Yasuno, Tetsuro Shinada

    The 13th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)  2018.11  IKCOC-13

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    Presentation type:Poster presentation  

    Venue:Rihga Royal Hotel, KYOTO, JAPAN  

  • Unusal Biosynthetic Reaction Mechanism of Terpenoids Invited International conference

    Tetsuro Shinada

    Sanyo Chemical Laboratory at Johor Bahru, Invited Seminar  2018.11  Sanyo Chemical Laboratory, Inc.

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    Venue:Malaysia,Johor Bahru  

  • Mechanistic Study of Terpene Synthase Using Deuterium Labelled Ligands Invited International conference

    Tetsuro Shinada

    INTERNATIONAL CONGRESS ON PURE & APPLIED CHEMISTRY (ICPAC) 2018 Langkawi  2018.10  Chemical Society of Malaysia

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    Venue: Langkawi, Malaysia  

  • 高度に官能基化されたモノフロログルシノール類の効率的合成 Domestic conference

    西村栄治、保野陽子、品田哲郎

    第62 回香料・テルペンおよび精油化学に関する討論会  2018.10  香料・テルペンおよび精油化学に関する討論会

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    Venue:長崎県長崎市、長崎大学文教キャンパス  

  • アリルアルコールを出発原料とするキノン誘導体のワンポット合成 Domestic conference

    保野陽子、鳥山陽平、小倉涼太、品田哲郎

    第60回天然有機化合物討論会  2018.09  天然有機化合物討論会

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    Venue:福岡県久留米市、久留米シティープラザ  

  • 酸触媒によるαヒドロキシαアルケニルシランの分子内Friedel-Crafts反応における不斉転写 Domestic conference

    久保田駿一,赤木航,池田直子,東野勝人,品田哲郎, 大船泰史,西村貴洋,坂口和彦

    第38回有機合成若手セミナー  2018.08  有機合成化学協会関西支部

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    Presentation type:Oral presentation (general)  

    Venue:関西学院大学西宮上ヶ原キャンパス  

  • β―ヒドロキシドーパの立体選択的合成 Domestic conference

    安田幸平,保野陽子,品田哲郎

    第38回有機合成若手セミナー  2018.08  有機合成化学協会関西支部

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    Presentation type:Oral presentation (general)  

    Venue:兵庫県西宮市、関西学院大学西宮上ヶ原キャンパス  

  • イソニトリルアルドール反応によるβ―ヒドロキシアミノ酸の立体選択的合成 Domestic conference

    福和真,保野陽子,品田哲郎

    第38回有機合成若手セミナー  2018.08  有機合成化学協会関西支部

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    Venue:兵庫県西宮市、関西学院大学西宮上ヶ原キャンパス  

  • SF-2132の全合成 Domestic conference

    関原あい,澤井瑛,保野陽子,品田哲郎

    第38回有機合成若手セミナー  2018.08  有機合成化学協会関西支部

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    Presentation type:Oral presentation (general)  

    Venue:兵庫県西宮市、関西学院大学西宮上ヶ原キャンパス  

  • Large-terpene 合成酵素の酵素的諸性質の解析と部位特異的変異 Domestic conference

    西 智之,菅原 啓 ,小川 佳央,高橋 宏忠,上田 大次郎,藤橋 雅宏,三木 邦夫,保野 陽子,品田 哲郎,佐藤 努

    第18回日本蛋白質科学会年会  2018.06  日本蛋白質科学会年会

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    Presentation type:Poster presentation  

    Venue:新潟県新潟市、朱鷺メッセ  

  • Large-terpene 合成酵素の構造と機能 Domestic conference

    藤橋雅宏,佐藤努,田中勇真,山本大輔,西智之,上田大次郎,村上瑞気 保野 陽子,関原あい、福和真,品田 哲郎,三木 邦夫

    第18回日本蛋白質科学会年会  2018.06  日本蛋白質科学会年会

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    Venue:新潟県新潟市、朱鷺メッセ  

  • テルペン生合成酵素反応機構の解明に資する鎖状テルペン基質およびプローブ合成法の開発 Invited Domestic conference

    品田哲郎

    新学術領域生合成リデザイン 第四回公開シンポジウム  2018.05  新学術領域生合成リデザイン総括班

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    Presentation type:Oral presentation (invited, special)  

    Venue:北海道大学理学部大講堂  

  • 単体ボヤCnemidocarpa ireneより得られた芳香族化合物群の構造と機能 Domestic conference

    宮古圭, 保野陽子, 品田哲郎, 藤田雅紀, 酒井隆一

    日本水産学会春季大会2018  2018.03  日本水産学会

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    Venue:東京都品川区 東京海洋大学品川キャンパス  

  • One-pot Synthesis of Anthraquinones by Sc(OTf)3-catalyzed Tandem Reaction Domestic conference

    Youhei Toriyama, Yoko Yasuno, Tetsuro Shinada

    日本化学会 第98回春季年会(2018)  2018.03  日本化学会

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    Presentation type:Oral presentation (general)  

    Venue:千葉県船橋市、日本大学理工学部船橋キャンパス  

  • 酸触媒によるα-ヒドロキシ-α-アルケニルシランの不斉転写型分子内Friedel-Crafts反応 Domestic conference

    久保田駿一、赤木航、池田直子、東野勝人・品田哲郎、大船 泰史、西村貴洋、坂口和彦

    日本化学会 第98回春季年会(2018)  2018.03  日本化学会

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    Presentation type:Oral presentation (general)  

    Venue:千葉県船橋市、日本大学理工学部船橋キャンパス  

  • Total Synthesis of SF-2132 (1) Domestic conference

    Akira Sawai, Ai Sekihara, Yoko Yasuno, Tetsuro Shinada

    日本化学会 第98回春季年会(2018)  2018.03  日本化学会

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    Presentation type:Oral presentation (general)  

    Venue:千葉県船橋市、日本大学理工学部船橋キャンパス  

  • Stereoselective Syntheses of β-Hydroxy Amino Acids by Isonitrile Aldol Reaction Domestic conference

    Kazuma Fuku, Yoko Yasuno, Tetsuro Shinada

    日本化学会 第98回春季年会(2018)  2018.03  日本化学会

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    Venue:千葉県船橋市、日本大学理工学部船橋キャンパス  

  • Synthetic Study of Phomopsin A Domestic conference

    Yuma Karita, Yoko Yasuno, Tetsuro Shinada

    日本化学会 第98回春季年会(2018)  2018.03  日本化学会

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    Venue:千葉県船橋市、日本大学理工学部船橋キャンパス  

  • Total Synthesis of SF-2132 (2) Domestic conference

    Ai Sekihara, Akira Sawai, Yoko Yasuno, Tetsuro Shinada

    日本化学会 第98回春季年会(2018)  2018.03  日本化学会

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    Presentation type:Oral presentation (general)  

    Venue:千葉県船橋市、日本大学理工学部船橋キャンパス  

  • Large-terpene合成酵素の酵素的諸性質の解析と部位特異的変異 Domestic conference

    菅原啓、西智之、小川佳央、高橋宏忠、上田大次郎、藤橋雅宏、三木邦夫、保野陽子、品田哲郎、佐藤努

    日本農芸化学会2018年度大会  2018.03  日本農芸化学会

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    Venue:愛知県名古屋市、名城大学  

  • Large-terpene合成酵素の結晶構造解析 Domestic conference

    藤橋雅宏、佐藤 努、田中 勇真、山本 大輔、西智之、上田大次郎、村上瑞気、保野陽子、関原あい、福和真、品田哲郎、三木 邦夫

    日本農芸化学会2018年度大会  2018.03  日本農芸化学

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    Venue:愛知県名古屋市、名城大学  

  • Stereoselective Synthesis of the Tripeptide of SF-2132 International conference

    Akira Sawai, Yoko Yasuno, Tetsuro Shinada

    The 9th OCARINA International Symposium Joint mini-symposiums on Structural Biology and Catalysis  2018.03  OCARINA, Osaka City University

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    Presentation type:Poster presentation  

    Venue:Osaka, Osaka City, Media Center, Osaka City University  

  • Total Synthesis of Antrimycin A and D Invited International conference

    Tetsuro Shinada

    INTERNATIONAL CONGRESS ON PURE & APPLIED CHEMISTRY (ICPAC) 2018 Siem Reap  2018.03  Chemiocal Society of Cambodia

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    Presentation type:Oral presentation (invited, special)  

    Venue:Spa, Siem Reap, Cambodia  

  • Synthetic Study of Deoxyustiloxin D International conference

    Kenta Sakai, Yoko Yasuno, Tetsuro Shinada

    The 9th OCARINA International Symposium Joint mini-symposiums on Structural Biology and Catalysis  2018.03  OCARINA, Osaka City University

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    Venue:Osaka, Osaka City, Media Center, Osaka City University  

  • Synthetic Study of Phomopsin A International conference

    Yuma Karita, Yoko Yasuno, Tetsuro Shinada

    The 9th OCARINA International Symposium Joint mini-symposiums on Structural Biology and Catalysis  2018.03  OCARINA, Osaka City University

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    Venue:Osaka, Osaka City, Media Center, Osaka City University  

  • Total Synthesis of SF-2132 International conference

    Ai Sekihara, Yoko Yasuno, Tetsuro Shinada

    The 9th OCARINA International Symposium Joint mini-symposiums on Structural Biology and Catalysis  2018.03  OCARINA, Osaka City University

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    Venue:Osaka, Osaka City, Media Center, Osaka City University  

  • One-pot Synthesis of Anthraquinones by Sc(OTf)3-catalyzed Tandem Reaction International conference

    Yohei Toriyama, Yoko, Yasuno, Tetsuro Shinada

    The 9th OCARINA International Symposium Joint mini-symposiums on Structural Biology and Catalysis  2018.03  OCARINA, Osaka City University

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    Venue:Osaka, Osaka City, Media Center, Osaka City University  

  • Stereoselective Syntheses of β-Hydroxy Amino Acids by Isonitrile Aldol Reaction International conference

    Kazuma Fuku, Yoko Yasuno, Tetsuro Shinada

    The 9th OCARINA International Symposium Joint mini-symposiums on Structural Biology and Catalysis  2018.03  OCARINA, Osaka City University

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    Presentation type:Poster presentation  

    Venue:Osaka, Osaka City, Media Center, Osaka City University  

  • Development of subtype selective ionotropic glutamate receptor antagonist by SAR study of kaitocephali Invited International conference

    Tetsuro Shinada

    Hakodate Special Seminar With Professor Geoffrey Swanson -Chemistry Meets Neuroscience-  2018.03 

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    Venue:Hokkaido, Hakodate, Hokkaido University  

  • UPLC-MS/MSを用いたカメムシ類の幼若ホルモンの構造決定 Domestic conference

    松本圭司, 児玉彩, 小滝豊美, 品田哲郎, 後藤慎介

    第62回日本応用動物昆虫学会  2018.03  日本応用動物昆虫学会

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    Venue:鹿児島県鹿児島市鹿児島大学  

  • ナガメの幼若ホルモンの同定と休眠への関与 Domestic conference

    児玉彩,松本圭司,品田哲郎,後藤慎介

    第63回日本応用動物昆虫学会大会  2018.03  日本応用動物昆虫学会

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    Venue:茨城県つくば市  

  • カメムシ類における幼若ホルモン構造の網羅的な解析 Invited Domestic conference

    松本圭司,嘉糠洋陸,齊木選射,沼田英治,小滝豊美,品田哲郎,後藤慎介

    第7回昆虫ホルモン談話会  2018.03  昆虫ホルモン談話会

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    Presentation type:Oral presentation (general)  

    Venue:茨城県つくば市  

  • 昆虫ってすごい!③毒を使う昆虫の知恵・ハチ毒の多様性 Invited Domestic conference

    品田哲郎

    西宮市生涯学習大学、宮水学園生物学講座【第11回】  2017.12  西宮市生涯学習大学、宮水学園

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    Presentation type:Public lecture, seminar, tutorial, course, or other speech  

    Venue:兵庫県西宮市大学交流センター  

  • Total Synthesis of Ustiloxin International conference

    Kazuma Fuku, Shunsuke Yamaguchi, Yoko Yasuno, Tetsuro Shinada

    11th International Symposium on Integrated Synthesis (ISONIS-11) 3rd International Symposium on Middle Molecular Strategy (ISMMS-3)  2017.11  新学術領域中分子戦略総括班

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    Presentation type:Oral presentation (general)  

    Venue: Hyogo, Awaji  

  • Efficient Synthesis of Anthraquinones by Sc(OTf)3-catalyzed Tandem Reaction International conference

    Yoko Yasuno, Yohei Toriyama, Ryota Ogura, Tetsuro Shinada

    11th International Symposium on Integrated Synthesis (ISONIS-11) 3rd International Symposium on Middle Molecular Strategy (ISMMS-3)  2017.11  新学術領域中分子戦略総括班

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    Presentation type:Poster presentation  

    Venue:Hyogo, Awaji  

  • ジアミノジカルボン酸類の触媒的不斉合成 Domestic conference

    保野陽子、水谷衣穂、末内優輝、品田哲郎

    第35回メディシナルケミストリーシンポジウム  2017.10  日本薬学会

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    Presentation type:Poster presentation  

    Venue:愛知県名古屋市、名古屋大学豊田講堂  

  • ハリナシミツバチ由来テトラゴカルボン類の構造決定 Domestic conference

    西村栄治、鈴木幸一、大船泰史、品田哲郎

    第59回天然有機化合物討論会  2017.09  天然有機化合物討論会

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    Presentation type:Poster presentation  

    Venue:北海道札幌市、わくわくホリデーホール  

  • アリルアルコールを出発原料とするタンデム触媒型Diels-Alder反応 Domestic conference

    鳥山陽平、保野陽子、品田哲郎

    第61回 香料・テルペンおよび精油化学に関する討論会  2017.09  香料・テルペンおよび精油化学に関する討論会

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    Presentation type:Oral presentation (general)  

    Venue:石川県野々市市、金沢工業大学  

  • 微生物が生産する天然有機化合物の合成と機能解析 Invited Domestic conference

    品田哲郎

    新潟大学コア・ステーション自然科学系附置植物・微生物科学研究センター共催公開セミナー  2017.09  新潟大学コア・ステーション自然科学系附置植物・微生物科学研究センター

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    Presentation type:Oral presentation (invited, special)  

    Venue:新潟県新潟市、新潟大学農学部  

  • SF-2132の合成研究 Domestic conference

    関原あい、澤井瑛、保野陽子、品田哲郎

    第37回有機合成若手セミナー「明日の有機合成を担う人のために」  2017.08  有機合成化学協会関西支部

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    Presentation type:Poster presentation  

    Venue:京都府京都市、 同志社大学寒梅館  

  • Ustiloxin-Dの全合成 Domestic conference

    保野陽子、山口俊介、坂井健太、福和真、品田哲郎

    第37回有機合成若手セミナー「明日の有機合成を担う人のために」  2017.08  有機合成化学協会関西支部

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    Presentation type:Poster presentation  

    Venue:京都府京都市、 同志社大学寒梅館  

  • 昆虫に着目した生物活性天然物の探索 Invited Domestic conference

    品田哲郎

    第12回化学生態学研究会  2017.06  化学生態学研究会

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    Presentation type:Oral presentation (invited, special)  

    Venue:北海道函館市、湯の川観光ホテル祥苑  

  • Cirratiomycin類の全合成 Domestic conference

    保野陽子、西村彰人、澤井瑛、品田哲郎

    第111回有機合成シンポジウム2017年【春】  2017.06  有機合成化学協会

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    Presentation type:Oral presentation (general)  

    Venue:岡山県岡山市、岡山大学(津島キャンパス)  

  • シクロラバンデュリル二リン酸合成酵素の結晶構造解析 Domestic conference

    小林 正弥、富田 武郎、品田 哲郎、西山 真、葛山 智久

    日本農芸化学会2017年度大会  2017.03  日本農芸化学会

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    Presentation type:Oral presentation (general)  

    Venue:京都府京都市、京都女子大  

  • Yuto Nishioka, You Yano, Naoto Kinashi, Natsumi Oku, Yohei Toriyama, Shigeo Katsumura, Tetsuro Shinada, Kazuhiko Sakaguchi Domestic conference

    Yuto Nishioka, You Yano, Naoto Kinashi, Natsumi Oku, Yohei Toriyama, Shigeo Katsumura, Tetsuro Shinada, Kazuhiko Sakaguchi,

    日本化学会第97回春季年会  2017.03  日本化学会

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    Presentation type:Oral presentation (general)  

    Venue:神奈川県横浜市、慶應義塾大学日吉キャンパス  

  • 4 + 2] Cyclization Reaction Using Trisubstituted Allyl Alcohols as Diene Precursors Domestic conference

    Yohei Toriyama, Ryota Ogura, Yoko Yasuno, Tetsuro Shinada

    日本化学会第97回春季年会  2017.03  日本化学会

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    Presentation type:Oral presentation (general)  

    Venue:神奈川県横浜市、慶應義塾大学日吉キャンパス  

  • Synthetic Study of Phomopsin A Domestic conference

    Yuma Karita, Yoko Yasuno, Testuro Shinada

    日本化学会第97回春季年会  2017.03  日本化学会

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    Presentation type:Oral presentation (general)  

    Venue:神奈川県横浜市、慶應義塾大学日吉キャンパス  

  • Synthetic Study of Deoxyustiloxin D Domestic conference

    Kenta Sakai, Yoko Yasuno, Tetsuro Shinada

    日本化学会第97回春季年会  2017.03  日本化学会

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    Presentation type:Oral presentation (general)  

    Venue:神奈川県横浜市、慶應義塾大学日吉キャンパス  

  • Synthetic Study of Ustiloxin D (2) Domestic conference

    Yoko Yasuno, Kazuma Fuku, Tetsuro Shinada

    日本化学会第97回春季年会  2017.03  日本化学会

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    Presentation type:Oral presentation (general)  

    Venue:神奈川県横浜市、慶應義塾大学日吉キャンパス  

  • Synthetic Study of Ustiloxin D (1) Domestic conference

    Shunsuke Yamaguchi, Yoko Yasuno, Tetsuro Shinada

    日本化学会第97回春季年会  2017.03  日本化学会

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    Presentation type:Oral presentation (general)  

    Venue:神奈川県横浜市、慶應義塾大学日吉キャンパス  

  • Catalytic Asymmetric Synthesis of Diamino Dicarboxylic Acids Domestic conference

    Iho Mizutani, Yoko Yasuno, Tetsuro Shinada

    日本化学会第97回春季年会  2017.03  日本化学会

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    Presentation type:Oral presentation (general)  

    Venue:神奈川県横浜市、慶應義塾大学日吉キャンパス  

  • Synthetic Study of SF-2132 Domestic conference

    Akira Sawai, Ai Sekihara, Yoko Yasuno, Tetsuro Shinada

    日本化学会第97回春季年会  2017.03  日本化学会

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    Presentation type:Oral presentation (general)  

    Venue:神奈川県横浜市、慶應義塾大学日吉キャンパス  

  • カメムシ類の幼若ホルモン:クサギカメムシおよびタガメの場合 Domestic conference

    小滝豊美, 後藤慎介, 松本圭司, 品田哲郎, 志賀向子, 門司麻衣子, 沼田英治

    第61回日本応用動物昆虫学会  2017.03  日本応用動物昆虫学会

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    Presentation type:Oral presentation (general)  

    Venue:鹿児島県鹿児島市鹿児島大学  

  • 脳神経関連疾病・がんの攻略にむけた医薬リードの創製研究 Invited Domestic conference

    品田哲郎

    メディカルジャパン:第4回日本医療総合展(大阪)  2017.02  日本医療総合展

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    Presentation type:Oral presentation (invited, special)  

    Venue:大阪府大阪市インテックス大阪  

  • カイトセファリンの構造活性相関:サブタイプ選択的イオンチャネル型グルタミン酸受容体リガンドの開発 Domestic conference

    保野陽子,濱田まこと,吉田侑矢,川崎昌紀, 大船泰史,品田哲郎

    第6回大阪市立大学バイオメディカルフォーラム  2017.02  大阪市立大学工学部

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    Presentation type:Poster presentation  

    Venue:大阪府大阪市あべのメディクス  

  • Antrimycin D の全合成 Domestic conference

    澤井 瑛,西村彰人,保野陽子,品田哲郎

    第6回バイオメディカルフォーラム  2017.02  大阪市立大学工学部

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    Presentation type:Poster presentation  

    Venue:大阪府大阪市あべのメディクス  

  • Phomopsin A の全合成研究 Domestic conference

    苅田祐馬,保野陽子,品田哲郎

    第6回バイオメディカルフォーラム  2017.02  大阪市立大学工学部

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    Presentation type:Poster presentation  

    Venue:大阪府大阪市あべのメディクス  

  • 最新の生物毒の多様性がおもしろい! その構造と機能、進化そして利用について 昆虫毒 その多様性と選択性 Domestic conference

    品田 哲郎

    日本生化学会大会・日本分子生物学会年会合同大会講演要旨集  2015.12  (公社)日本生化学会

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    Presentation type:Oral presentation (general)  

  • Bacillus clausiiにおけるセスタテルペン、Head-to-tail型トリテルペン、セスクアテルペンの生合成 多機能性酵素の同定とイソプレノイド代謝物の解析 Domestic conference

    村上 瑞気, 山鹿 宏彰, 遠塚 悠輔, 品田 哲郎, 佐藤 努

    日本生物工学会大会講演要旨集  2015.09  (公社)日本生物工学会

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    Presentation type:Oral presentation (general)  

  • ハチ毒の多様性 Domestic conference

    品田 哲郎

    日本生化学会大会プログラム・講演要旨集  2011.09  (公社)日本生化学会

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    Presentation type:Oral presentation (general)  

  • ショウガ科植物Kaempferia parviflora根茎のキサンチンオキシダーゼ阻害作用 Domestic conference

    村田 和也, 出口 貴浩, 伊藤 仁久, 松田 秀秋, 中尾 紀久世, 新谷 卓弘, 藤田 貴則, 東野 正行, 吉岡 百合, 松村 晋一, 田中 里佳, 品田 哲郎, 大船 泰史

    日本薬学会年会要旨集  2011.03  (公社)日本薬学会

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    Presentation type:Oral presentation (general)  

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Grant-in-Aid for Scientific Research

  • Synthesis of Artificial Terpenoids Using Terpene Cyclase

    Grant-in-Aid for Transformative Research Areas (A)  2024

  • カメムシ幼若ホルモンの合成・受容機構とその進化過程の解明

    Grant-in-Aid for Scientific Research(B)  2024

  • 脱水素クロスカップリングを利用した機能性配向基の開発とそのペプチド合成への応用

    Grant-in-Aid for Scientific Research(B)  2020.04

  • Identification of new target molecule using natural products: Toward development of anti tuberculosis molecules

    Grant-in-Aid for Scientific Research(B)  2020.04

  • Functional analysis of terpene synthases and its application to the synthesis of unusual terpenoids

    Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)  2019.04

  • Synthetic study of chiral compounds by taking advantage of an umpolung approach

    Grant-in-Aid for Scientific Research(C)  2017.04

  • Synthetic Study of Acyclic Terpene Probes to Elucidate the Reaction Mechanism of Terpenoid Biosynthesis

    Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)  2017.04

  • Exploitation of niches and diversification of organisms by utilising invisible light: the new research field of photogeobiology

    Grant-in-Aid for Challenging Research (Pioneering)/(Exploratory)  2016.04

  • Development of new anchor molecule to fix biologically active molecules on cell surface

    Grant-in-Aid for Challenging Research (Pioneering)/(Exploratory)  2015.04

  • Molecular and neural mechanisms of photoperiodism in the bean bug, Riptortus pedestris

    Grant-in-Aid for Scientific Research(B)  2014.04

  • Development of novel synthetic reactions based on mutual cooperation of nitrogen-oxygen bonds and multiple bonds

    Grant-in-Aid for Scientific Research(C)  2014.04

  • Creation of novel terpenoids from biosynthetic study on sesquarterpene

    Grant-in-Aid for Scientific Research(C)  2013.04

  • Stereoselective synthesis of mono- and di-substituted dehydroamino acids and its application to the natural product synthesis and chemical biology.

    Grant-in-Aid for Scientific Research(B)  2013.04

  • Structure determination of juvenile hormone in cicadas-an attempt to develop insecticides specific to planthoppers and leafhoppers

    Grant-in-Aid for Scientific Research(C)  2012.04

  • Structure and function of an improving factor in hippocampal impairment originated from the silkworm-parasitic fungus (Paecilomyces tenuipes) and practical use for human brain

    Grant-in-Aid for Scientific Research(S)  2011.04

  • Chemical biology using natural products

    Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)  2011.04

  • Study toward Development Ionotropic Glutamate Receptore Subytpe Selective Ligand

    Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)  2011.04

  • 鎖状テルペン類の自在合成法の開発とその応用

    新学術領域研究(研究領域提案型)  2011

  • Synthesis of α-Amino Squaric Acid Incorporated Peptides and Their Biological Activities

    Grant-in-Aid for Scientific Research(B)  2009

  • Central mechanism controlling photoperiodism and diapause in stink bugs.

    Grant-in-Aid for Scientific Research(B)  2008

  • Development of Novel Ligands for Glutamate Receptors Using Natural Neurotoxins as the Structural Motif

    Grant-in-Aid for Scientific Research(A)  2008

  • Regulatory mechanisms of insect ovary-development : proteases involved in oosorption and JHSB3, a new juvenile hormone controlling oosorption in Plautia stali.

    Grant-in-Aid for Scientific Research(C)  2007

  • Chemistry of Sq group containing amino acid (ASQ): Incorporation of ASQ into peptides and their function

    Grant-in-Aid for Scientific Research(C)  2006

  • クマゼミの湿度による艀化誘導機構の研究

    萌芽研究  2006

  • DESIGN AND SYNTHESIS OF NOVEL EXCITATORY AMINO ACIDS BASED ON THE TOTAL SYNTHESIS OF NATURAL NEE TROTOXTNS

    Grant-in-Aid for Scientific Research(A)  2004

  • 配座及び官能基制御に基づく高活性神経リガンドの開発

    Grant-in-Aid for Scientific Research on Priority Areas  2004

  • Synthesis and its function of novel squaric acid containing amino acids.

    Grant-in-Aid for Scientific Research(C)  2003

  • 光学活性テトロドトキシン類の全合成研究

    Grant-in-Aid for Young Scientists(B)  2001

  • 短寿命活性種オルソ酸の構造安定化:篭状オルソ酸の合成と活性

    萌芽的研究  2000

  • 高度生体応答分子の全合成

    Grant-in-Aid for Scientific Research on Priority Areas  1997

  • スクアリン酸含有アミノ酸類の合成研究

    萌芽的研究  1997

  • 天然物合成を指向した含窒素4級炭素を含む3連続不斉中心構築法の開発

    奨励研究(A)  1997

  • 9,13位修飾レチナ-ル類の合成

    奨励研究(A)  1995

▼display all

Outline of education staff

  • 担当科目
    全学共通科:基礎化学実験I、入門化学、
    専門科目:有機化学2,4、化学実験3,4、特別研究
    大学院科目:基幹有機化学、前期、後期特別研究、機能分子科学演習、機能分子科学ゼミナール

Charge of on-campus class subject

  • 化学実験1

    2024   Weekly class   Undergraduate

  • 研究企画ゼミナール

    2024   Intensive lecture   Graduate school

  • 化学特別研究1A

    2024   Intensive lecture   Graduate school

  • 化学特別演習2A

    2024   Intensive lecture   Graduate school

  • 化学特別演習1A

    2024   Intensive lecture   Graduate school

  • 化学特別研究2A

    2024   Intensive lecture   Graduate school

  • 化学特別演習4A

    2024   Intensive lecture   Graduate school

  • 化学特別演習3A

    2024   Intensive lecture   Graduate school

  • 化学特別研究5A

    2024   Intensive lecture   Graduate school

  • 化学特別研究4A

    2024   Intensive lecture   Graduate school

  • 化学特別研究3A

    2024   Intensive lecture   Graduate school

  • 化学特別演習5A

    2024   Intensive lecture   Graduate school

  • 化学セミナー

    2024   Intensive lecture   Undergraduate

  • 化学実験Ⅱ

    2024   Weekly class   Undergraduate

  • 化学実験Ⅰ

    2024   Weekly class   Undergraduate

  • 機能物質科学演習

    2020     Graduate school

  • 機能有機化学特論1

    2020     Graduate school

  • 有機化学IV

    2020     Undergraduate

  • 化学セミナー

    2020     Undergraduate

  • 入門化学

    2020     Undergraduate

  • 特別演習

    2020     Undergraduate

  • 有機化学4

    2019     Undergraduate

  • 有機化学2

    2019     Undergraduate

  • 入門化学

    2019     Undergraduate

  • 化学実験III

    2019     Undergraduate

  • 前期特別研究

    2019     Graduate school

  • 後期特別研究

    2019     Graduate school

  • 基幹有機化学

    2019     Graduate school

  • 基礎化学実験I

    2019     Undergraduate

  • 機能物質科学演習

    2019     Graduate school

  • 現代科学と人間

    2018     Undergraduate

  • 後期特別研究

    2018     Graduate school

  • 前期特別研究

    2018     Graduate school

  • 基幹有機化学

    2018     Graduate school

  • 有機化学4

    2018     Undergraduate

  • 有機化学2

    2018     Undergraduate

  • 入門化学

    2018     Undergraduate

  • 基礎化学実験I

    2018     Undergraduate

  • 化学実験III

    2018     Undergraduate

  • 機能物質科学演習

    2018     Graduate school

  • 化学産業論

    2018     Graduate school

  • 体験で知る自然と技術

    2017     Undergraduate

  • 現代科学と人間

    2017     Undergraduate

  • 基礎化学実験II

    2017     Undergraduate

  • 基礎化学実験I

    2017     Undergraduate

  • 化学実験Ⅳ

    2017     Undergraduate

  • 化学実験Ⅲ

    2017     Undergraduate

  • 有機化学II

    2017     Undergraduate

  • 基幹有機化学

    2017     Graduate school

  • 後期特別研究

    2017     Graduate school

  • 前期特別研究

    2017     Graduate school

  • 機能分子科学演習

    2017     Undergraduate

▼display all

Charge of off-campus class subject

  • 化学セミナー

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

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    Country:Japan

  • 研究企画ゼミナール

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

     More details

    Country:Japan

  • 化学特別研究5A

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

     More details

    Country:Japan

  • 化学特別研究4A

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

     More details

    Country:Japan

  • 化学特別研究3A

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

     More details

    Country:Japan

  • 化学特別研究2A

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

     More details

    Country:Japan

  • 化学特別研究1A

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

     More details

    Country:Japan

  • 化学特別演習5A

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

     More details

    Country:Japan

  • 化学特別演習4A

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

     More details

    Country:Japan

  • 化学特別演習3A

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

     More details

    Country:Japan

  • 化学特別演習2A

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

     More details

    Country:Japan

  • 化学特別演習1A

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

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    Country:Japan

  • 化学実験Ⅱ

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

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    Country:Japan

  • 化学実験Ⅰ

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

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    Country:Japan

  • 化学実験1

    2024.04
    -
    2025.03
    Institution:Osaka Metropolitan University

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    Country:Japan

  • 化学セミナー

    2020.04
    -
    2021.03
    Institution:Osaka City University

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    Country:Japan

  • 機能物質科学演習

    2020.04
    -
    2021.03
    Institution:Osaka City University

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    Country:Japan

  • 機能有機化学特論1

    2020.04
    -
    2021.03
    Institution:Osaka City University

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    Country:Japan

  • 有機化学IV

    2020.04
    -
    2021.03
    Institution:Osaka City University

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    Country:Japan

  • 特別演習

    2020.04
    -
    2021.03
    Institution:Osaka City University

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    Country:Japan

  • 化学産業論

    2018.04
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    2019.03
    Institution:Osaka City University

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    Country:Japan

  • 現代科学と人間

    2018.04
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    2019.03
    Institution:Osaka City University

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    Country:Japan

  • 反応有機化学論II

  • 薬用資源学特論

  • 薬用資源学特論

  • 反応有機化学論II

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Social Activities ⇒ Link to the list of Social Activities

  • 博物館協会連携講座

    Role(s): Lecturer

    Type: University open house, Cooperation business with The administrative, educational institutions, etc.

    博物館協会連携講座  文化交流センター  2013.12

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    Audience: General public

    Number of participants:40(人)

Visiting Lectures ⇒ Link to the list of Visiting Lectures

  • 化学発光の不思議

    Category:Modern system science (knowledge information system, environmental system, educational welfare, psychology), Commerce (management, public management), Economics, Law (law, politics, administration), Literature (literature, philosophy, history, art, human behavior, language, culture, society / gender), Science (mathematics, physics, chemistry, biology, geology, biochemistry), Engineering (machinery, electronics / physics, electrical / electronics, electrical information, chemical biotechnology, architecture, cities (civil engineering / environment), material chemistry, aerospace, marine systems, applied chemistry, chemistry, materials), Life sciences (food, nutrition science, living environment, human welfare), Agricultural science (applied biology, biofunctional chemistry, green space environmental science), Medicine (medical care, rehabilitation, health exercise science, physical fitness / training, sports practice science), Nursing (nursing, sex education), Veterinary

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    Audience:General

    文系向け実験授業として、また、高校生向けの実験授業の題材です。化学発光そのものを体感する実験と、それを使った応用実験を行うことで、化学の不思議や面白さを学んでもらう。
    化学発光を体感するとともに、目に見えない化学反応や酵素反応を可視化することでその原理を学ぶ。
    化学発光の実験は、小学校や高校でも出前授業したことがある。その応用の部分については、中学生や高校生以上が適当かもしれない。何をどこまでやるかで、コマ数や、難易度は変わる。実験する部分が多くなるのであれば、実験をする環境が必要。

  • くすりの話

    Category:Modern system science (knowledge information system, environmental system, educational welfare, psychology), Commerce (management, public management), Economics, Law (law, politics, administration), Literature (literature, philosophy, history, art, human behavior, language, culture, society / gender), Science (mathematics, physics, chemistry, biology, geology, biochemistry), Engineering (machinery, electronics / physics, electrical / electronics, electrical information, chemical biotechnology, architecture, cities (civil engineering / environment), material chemistry, aerospace, marine systems, applied chemistry, chemistry, materials), Life sciences (food, nutrition science, living environment, human welfare), Agricultural science (applied biology, biofunctional chemistry, green space environmental science), Medicine (medical care, rehabilitation, health exercise science, physical fitness / training, sports practice science), Nursing (nursing, sex education), Veterinary

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    Audience:General

    理系教員が行う文系向け授業の題材につかったもので。13回の講義内容があります。大きくは、1)薬が私たちにどのように働きかけるのかについて、体の仕組みと薬という物質の成り立ちから考える授業構成と、2)漢方薬と現代薬の比較、歴史、補完性についての解説です。Q&Aを交えるバージョンもあります。
    薬についての基礎知識を分かり易く解説する。
    講義回数、難易度は、適宜調整できるが、分かりやすい内容にするには、1回はきついかもしれない。化学式などは一切つかわない内容にしてある。

Foreigner acceptance

  • 2020

    foreigners accepted :0

    International Students :0