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Total Synthesis of Antitumor Marine Polyethers for Exploring Mode of Action

Research Project

Project/Area Number 18350021
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionOsaka University

Principal Investigator

大石 徹  Osaka University, 大学院理学研究科, 准教授 (90241520)

Project Period (FY) 2006 – 2008
Project Status Completed (Fiscal Year 2008)
Budget Amount *help
¥12,310,000 (Direct Cost: ¥10,600,000、Indirect Cost: ¥1,710,000)
Fiscal Year 2008: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Fiscal Year 2007: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2006: ¥4,900,000 (Direct Cost: ¥4,900,000)
Keywords全合成 / ポリエーテル / 生理活性 / 抗腫瘍性 / 海産毒 / 天然物 / 収束的合成 / オレフィンメタセシス / マイクロフローリアクター / 抗腫瘍活性
Research Abstract

海洋プランクトンが生産する微量成分であるイェッソトキシン(YTX)は,分子量が千を超える複雑な有機化合物であり,腫瘍細胞に対してアポトーシス(細胞死)を誘導する。YTXがどの様な蛋白質に作用し,またどの様な機構で生物活性を発現するのかを明らかにするため,複雑な構造を有するYTXを効率的に化学合成する方法の開発に成功した。この方法を用いることで,YTXや他の類似した化合物を合成することが可能になる。

Report

(4 results)
  • 2008 Annual Research Report   Final Research Report ( PDF )
  • 2007 Annual Research Report
  • 2006 Annual Research Report
  • Research Products

    (30 results)

All 2008 2007 2006 Other

All Journal Article (21 results) (of which Peer Reviewed: 15 results) Presentation (7 results) Remarks (2 results)

  • [Journal Article] Interaction of ladder-shaped polyethers with transmembrane α-helix of glycophorin A as evidenced by saturation transfer difference NMR and surface plasmon resonance2008

    • Author(s)
      Satoru Ujihara, Tohru Oishi, KoheKeiichi Konoki, Nobuaki Matsumori, Michio Murata, Yasukatsu Oshima, Saburo Aimoto
    • Journal Title

      Bioorg. Med. Chem. Lett. 18

      Pages: 6115-6118

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Convegent Synthesis of the A-J Ring System of Yessotoxin2008

    • Author(s)
      Kohei Torikai, Koji Watanabe, Hiroaki Minato, Tomoyoshi Imaizumi, Michio Murata, Tohru Oishi,
    • Journal Title

      Synlett

      Pages: 2368-2372

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Convergent Synthesis and Biological Activity of the WXYZA'B'C' Ring System of Maitotoxin2008

    • Author(s)
      Tohru Oishi, Futoshi Hasegawa, Kohei Torikai, Keiichi Konoki, Nobuaki Matsumori, Michio Murata
    • Journal Title

      Synlett,Org. Lett., 10

      Pages: 3599-3602

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Design and Synthesis of Ladder-Shaped Tetracyclic, Heptacyclic, and Decacyclic Ethers and Evaluation of the Interaction with Transmembrane Proteins2008

    • Author(s)
      Kohei Torikai, Tohru Oishi, Satoru Ujihara, Nobuaki Matsumori, Keiichi Konoki, Michio Murata, Saburo Aimoto
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 10217-10226

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Convergent Synthesis of the A-J Ring System of Yessotoxin2008

    • Author(s)
      Kohei Torikai
    • Journal Title

      Synlett

      Pages: 2368-2372

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Convergent Synthesis and Biological Activity of the WXYZA'B'C' Ring System of Maitotoxin2008

    • Author(s)
      Tohru Oishi
    • Journal Title

      Org. Lett. 10

      Pages: 3599-3602

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design and Synthesis of Ladder-Shaped Tetracyclic, Heptacyclic, and Decacyclic Ethers and Evaluation of the Interaction with Transmembrane Proteins2008

    • Author(s)
      Kohei Torikai
    • Journal Title

      J. Am. Chem. Soc. 13 0

      Pages: 10217-10226

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the JK Ring Fragments of Yessotoxin and 42,43,44,45,46,47,55-Heptanor-41-Oxoyessotoxin2007

    • Author(s)
      Koji Watanabe, Hiroaki Minato, Michio Murata, Tohru Oishi
    • Journal Title

      Heterocycles, 72

      Pages: 207-212

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the JK ring fragments of yessotoxin and 42,43,44,45,46,47,55-heptanor-41-oxoyessotoxin.2007

    • Author(s)
      Koji Watanabe
    • Journal Title

      Heterocycles 72

      Pages: 207-212

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Amphotericin B covalent dimers with carbonyl-amino linkage: a newprobe for investigating ion channel assemblies.2007

    • Author(s)
      Yuichi Umegawa
    • Journal Title

      Tetrahedron Lett. 48

      Pages: 3393-3396

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] X-ray crystallographic and biochemical characterization of the inhibitory action of an imidazole-dioxolane compound on heme oxygenase.2007

    • Author(s)
      Masakazu Sugishima
    • Journal Title

      Biochemistry 46

      Pages: 1860-1867

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Artificial Ladder-Shaped Polyethers Containing a 6/7 cis-Fused Ring System2006

    • Author(s)
      Kohei Torikai, Hiroshi Yari, Michio Murata, Tohru Oishi
    • Journal Title

      Heterocycles, 70

      Pages: 161-167

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Design and Synthesis of an Artificial Ladder-Shaped Polyether that Interacts with Glycophorin A2006

    • Author(s)
      Kohei Torikai, Hiroshi Yari, Megumi Mori, Satoru Ujihara, Nobuaki Matsumori, Michio Murata, Tohru Oishi
    • Journal Title

      Bioorg. Med. Chem. Lett., 16

      Pages: 6355-6359

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Conbergent Synthesisi of the CDEF Ring System of yessotoxin via α-Cyano Ethers2006

    • Author(s)
      Tohru Oishi, Miho Sizuki, Koji Watanabe, Michio Murata
    • Journal Title

      Heterocycles, 69

      Pages: 91-98

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the ABC and IJ Ring Fragments of Yessotoxin2006

    • Author(s)
      Tohru Oishi, Miho Suzuki, Koji Watanabe, Michio Murata
    • Journal Title

      Tetrahedron Lett., 47

      Pages: 3975-3978

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the ABC and IJ ring fragments of yessotoxin.2006

    • Author(s)
      Tohru Oishi
    • Journal Title

      Tetrahedron Lett. 47(24)

      Pages: 3975-3978

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Synthesis of 28-^<19>F-amphotericin B methyl ester2006

    • Author(s)
      Hiroshi Tsuchikawa
    • Journal Title

      Tetrahedron Lett. 47(35)

      Pages: 6187-6191

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Convergent synthesis of the CDEF ring system of yessotoxin via α-cyano ethers.2006

    • Author(s)
      Tohru Oishi
    • Journal Title

      Heterocycles 69

      Pages: 91-98

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Design and synthesis of an artificial ladder-shaped polyether that interacts with glycophorin A.2006

    • Author(s)
      Kohei Torikai
    • Journal Title

      Bioorg. Med. Chem. Lett. 16(24)

      Pages: 6355-6359

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities.2006

    • Author(s)
      Nagy Morsy
    • Journal Title

      Bioorg. Med. Chem. 14(19)

      Pages: 6548-6554

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Synthesis of artificial ladder-shaped polyethers containing a 6/7 cis-fused ring system.2006

    • Author(s)
      Kohei Torikai
    • Journal Title

      Heterocycles 70

      Pages: 161-167

    • Related Report
      2006 Annual Research Report
  • [Presentation] Synthesis of fluorine labeled natural products for solid-state NMR measurements2008

    • Author(s)
      Tohru Oishi
    • Organizer
      236th ACS National Meeting
    • Place of Presentation
      Philadelphia, USA
    • Year and Date
      2008-08-17
    • Related Report
      2008 Annual Research Report
  • [Presentation] Synthetic Studies of Yessotoxin2007

    • Author(s)
      Tohru Oishi
    • Organizer
      International Symposium on Catalysts and Fine Chemicals
    • Place of Presentation
      Nanyang Technoligical University Singapore
    • Year and Date
      2007-12-17
    • Related Report
      2008 Final Research Report
  • [Presentation] Synthetic Studies of Yessotoxin2007

    • Author(s)
      Tohru Oishi
    • Organizer
      International Symposium on Catalysts and Fine Chemicals
    • Place of Presentation
      Nanyang Technological University,シンガポール
    • Year and Date
      2007-12-17
    • Related Report
      2007 Annual Research Report
  • [Presentation] 生体機能解明を志向した生理活性物質の設計と合成2007

    • Author(s)
      大石 徹
    • Organizer
      第2回理研シンポジウム「有機合成化学のフロンティア」
    • Year and Date
      2007-07-06
    • Related Report
      2008 Final Research Report
  • [Presentation] 膜蛋白質との相互作用解明を志向した梯子状ポリエーテルの設計と合成2007

    • Author(s)
      大石 徹徹,鳥飼浩平,長谷川太志,今泉智禎,此木敬一,松森信明,村田道雄
    • Organizer
      日本ケミカルパイオロジー研究会第2回年会京都大学百周年記念ホール
    • Year and Date
      2007-05-09
    • Related Report
      2008 Final Research Report
  • [Presentation] Synthetic Studies of Natural and Artificial Ladder-shaped Polyethers for Exploring Biological Functions2006

    • Author(s)
      Tohru Oishi
    • Organizer
      Sendai Postsymposium of ICOB-5 & ISCNP-25 IUPAC International Conference on Biodiversity and Natural Products
    • Place of Presentation
      Sendai, Japan
    • Year and Date
      2006-07-30
    • Related Report
      2008 Final Research Report
  • [Presentation] 膜蛋白質と相互作用する生体機能分子の合成と機能解析2006

    • Author(s)
      大石 徹
    • Organizer
      特定領域研究第2回公開シンポジウム
    • Place of Presentation
      仙台国際センター
    • Year and Date
      2006-06-30
    • Related Report
      2008 Final Research Report
  • [Remarks]

    • URL

      http://www.ch.wani.osaka-u.ac.jp/lab/murata/

    • Related Report
      2008 Annual Research Report
  • [Remarks]

    • URL

      http://www.ch.wani.osaka-u.ac.jp/lab/murata/

    • Related Report
      2007 Annual Research Report

URL: 

Published: 2006-04-01   Modified: 2016-04-21  

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