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Synthesis and SAR study of novel tetrodotoxin analogs.

Research Project

Project/Area Number 19750147
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemistry related to living body
Research InstitutionKanagawa University

Principal Investigator

AKAI Shoji  Kanagawa University, 工学部, 助教 (00322537)

Research Collaborator SATO Kenichi  神奈川大学, 工学部, 教授 (40114871)
Project Period (FY) 2007 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥3,680,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥480,000)
Fiscal Year 2009: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2008: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2007: ¥1,600,000 (Direct Cost: ¥1,600,000)
Keywords有機化学 / 生理活性 / 合成化学 / テトロドトキシン
Research Abstract

Tetrodotoxin (TTX), one of the best-known marine toxins, was originally isolated from puffer fish. It is known that TTX selectively combines with elements of the sodium channel, thus inhibiting its function in the cell membrane. Therefore, TTX is utilized as a tool for the analysis of various vital phenomena, which occur via the sodium channel. Therefore, it is considered very important to synthesize larger amounts of TTX and its analogues than those available now. In this work, syntheses of optically active- and partially deoxygenated-TTX from D-glucose and myo-inositol in practical amounts, and its stable isotopic labeling are studied. As a result, a crucial key compound for synthesizing the above target compounds is prepared from D-glucose in 24-28 steps. Total synthesis of 8- and 9-deoxyTTX from the key compounds and its stable isotope labeling are now in progress.

Report

(4 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • 2007 Annual Research Report
  • Research Products

    (13 results)

All 2010 2009 2008 2007

All Journal Article (9 results) (of which Peer Reviewed: 9 results) Presentation (2 results) Book (2 results)

  • [Journal Article] Total Synthesis of (-)-Tetrodotoxin from D-Glucose: A New Route to Multi-Functionalized Cyclitol Employing the Ferrier(II) Reaction toward (-)-Tetrodotoxin2010

    • Author(s)
      S. Akai, H. Seki, N. Sugita, T. Kogure, N. Nishizawa, K. Suzuki, Y. Nakamura, Y. Kajihara, J. Yoshimura, K. Sato
    • Journal Title

      Bull. Chem Soc. Jpn 83(3)

      Pages: 279-287

    • NAID

      10027172694

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (-)-Tetrodotoxin from D-Glucose : A New Route to Multi-Functionalized Cyclitol Employing the Ferrier(II) Reaction toward (-)-Tetrodotoxin.2010

    • Author(s)
      Akai, Shoji ; Sato, Ken-ichi, 他8名
    • Journal Title

      Bulletin of the Chemical Society of Japan 83

      Pages: 279-287

    • NAID

      10027172694

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Syntheses of Bistratamides J, E, and H from Two Types of ΔAla-Containing Oligopeptides2008

    • Author(s)
      H. Suzuki, M. Andoh, Y. Yonezawa, S. Akai, C. Shin, K. Sato
    • Journal Title

      Bull. Chem. Soc. Jpn 81(4)

      Pages: 495-501

    • NAID

      10021074971

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective and Efficient Total Synthesis of Optically Active Tetrodotoxin from D-Glucose2008

    • Author(s)
      K. Sato, S. Akai, H. Shoji, N. Sugita, S. Yoshida, Y. Nagai, K. Suzuki, Y. Nakamura, Y. Kajihara, M. Funabashi, J. Yoshimura
    • Journal Title

      J. Org. Chem 73(4)

      Pages: 1234-1242

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of (-)-Tetrodotoxin2008

    • Author(s)
      K. Sato, S. Akai, H. Shoji, N. Sugita, S. Yoshida, Y. Nagai, K. Suzuki, Y. Nakamura, Y. Kajihara, M. Funabashi, J. Yoshimura
    • Journal Title

      Synfacts 8

      Pages: 749-749

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of (-)-Tetrodotoxin2008

    • Author(s)
      K. Sato, S. Akai, 他9名
    • Journal Title

      Synfacts 8

      Pages: 749-749

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Syntheses of Bistratamides J, E, and H from Two Types of AAIa -Containing Oligopeptides2008

    • Author(s)
      H. Suzud, S. Akai, 他6名
    • Journal Title

      Bull. Chem. Soc. Jpn 4

      Pages: 495-501

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective and Efficient Total Synthesis of Optically Active Tetrodotoxin from D-Glucose.2008

    • Author(s)
      K. Sato, S. Akai et al.
    • Journal Title

      The Journal of Organic Chemistry 73(4)

      Pages: 1234-1242

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A novel method for regioselective ring-opening reduction of 4,6-O-benzylidene hexopyranoside derivatives using CoCI_2 and BH_3・THF2007

    • Author(s)
      S. Akai, K. Sato et al.
    • Journal Title

      Tetrahedron Letters 48(17)

      Pages: 3103-3104

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Presentation] Bu_4NNO_2-Boc_2O/pyridineを用いるN-Phenylcarbamoyl基の改良脱保護法2009

    • Author(s)
      赤井昭二, 他2名
    • Organizer
      第58回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      長岡技術科学大学(新潟)
    • Year and Date
      2009-11-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] Bu4NNO2-Boc2O/pyridineを用いるN-Phenylcarbamoyl基の改良脱保護法2009

    • Author(s)
      赤井昭二, 田中李佳, 佐藤憲一
    • Organizer
      第58回有機合成化学協会関東支部シンポジウム-新潟(長岡)シンポジウム-
    • Place of Presentation
      新潟(長岡)
    • Related Report
      2009 Final Research Report
  • [Book] Stereoselective synthesis of tetrodotoxin from carbohydtates.(Fukugo Toshistsu no Kagaku to Saishin Oyo Gijutsu)2009

    • Author(s)
      Ken-ichi Sato; Shoji Akai
    • Related Report
      2009 Final Research Report
  • [Book] 複合糖質の化学と最新応用技術(Glycoconjugate Chemistry and Modern Applied Technology)2009

    • Author(s)
      Sato, Ken-ichi ; Akai, Shoji, 他66名
    • Total Pages
      298
    • Publisher
      シーエムシー出版
    • Related Report
      2009 Annual Research Report

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Published: 2007-04-01   Modified: 2016-04-21  

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