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2009 Fiscal Year Final Research Report

Synthesis and SAR study of novel tetrodotoxin analogs.

Research Project

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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
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.

  • Research Products

    (6 results)

All 2010 2009 2008

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (1 results) Book (1 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

    • 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

    • 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

    • 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

    • Peer Reviewed
  • [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)
    • Year and Date
      20091200
  • [Book] Stereoselective synthesis of tetrodotoxin from carbohydtates.(Fukugo Toshistsu no Kagaku to Saishin Oyo Gijutsu)2009

    • Author(s)
      Ken-ichi Sato; Shoji Akai
    • Total Pages
      113-128

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Published: 2011-06-18   Modified: 2016-04-21  

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