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Complete Structure Elucidation of Maitotoxin

Research Project

Project/Area Number 06453211
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field Bioorganic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

MURATA Michio  The University of Tokyo, Graduate School of Science, Associate Professor, 大学院・理学系研究科, 助教授 (40183652)

Co-Investigator(Kenkyū-buntansha) SASAKI Makoto  The University of Tokyo, Graduate School of Science, Research Associate, 大学院・理学系研究科, 助手 (80235267)
安元 健  東北大学, 農学部, 教授 (20011885)
Project Period (FY) 1994 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥4,800,000 (Direct Cost: ¥4,800,000)
Fiscal Year 1995: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1994: ¥3,900,000 (Direct Cost: ¥3,900,000)
Keywordsmaitotoxin / marine natural products / polyether / dinoflagellate / NMR / spin coupling constants / stereoselective synthesis / absolute stereochemistry / 立体選択的合成 / 超活性 / NMR分光学
Research Abstract

Maitotoxin is the most toxic and largest natural product among non-biopolymers known to date. Althought most of stereogenic centers in ring systems was assigned by simple NOE experiments, the complete structural elucidation was hampered by the presence of asymmetric centers in acyclic portions, particularly, C1-C14 and C134-C142 side chains. The present study has successfully elucidated the total sturcture by menas of NMR spectroscopy coupled with stereoselective synthesis of the fragmental structures. In the NMR analysis, we focused on the carbon-proton copling constants, which provided important dihedral angles for the conformational and configurational assignments of the side chains. The absolute stereochemistry has been also assigned by the synthesis of all the possible stereoisomer for fragment C,which was generated by periodate degradation of maitotoxin.

Report

(3 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • Research Products

    (19 results)

All Other

All Publications (19 results)

  • [Publications] Michio Murata: "Structure and partial stereochemical assignments for maitotoxin, the most toxic and largest natural non-biopolymer" Journal of the American Chemical Society. 116. 7098-7107 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Sasaki: "Synthesis and stereochemical confirmation of the cis-fused L/M and N/O ring systems of maitotoxin" Tetrahedron Letters. 35. 5023-5026 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Satake: "Structural confirmaiton of maitotoxin on the basis of complete ^<13> NMR assignments and three-dimensional PFG NOESY-HMQC spectrum." Journal of the American Chemical Society. 117. 7019-7020 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Sasaki: "Synthetic approach toward complete structure determination of maitotoxin. Stereochemical assignment of the C63-C68 acyclic linkages." Tetrahedron Letters. 36. 9007-9010 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Sasaki: "Stereochemical assignment of the C35-C39 acyclic likage in maitotoxin: Completion of stereochemical determination of C15-C134" Tetrahedron Letters. 36. 9011-9014 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Nobuaki Matsumori: "Long-range carbon-proton coupling constants for stereochemical assignment of acyclic atructures in natural products: configuration of the C5-C9 portion of maitotoxin" Tetrahedron Letters. 37. 1269-1272 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Michio Murata: "Structure and partial stereochemical assignments for maitotoxin, the most toxic and largest natural non-biopolymer." J.Am.Chem.Soc. 116. 7098-7107 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Sasaki: "Synthesis and stereochemical confirmation of the cis-fused L/M and N/O ring systems of maitotoxin." Tetrahedron Lett.35. 5023-5026 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Satake: "Structural confirmation of maitotoxin on the basis of complete ^<13>CNMR assignments and three-dimensional PFG NOESY-HMQC spectrum." J.Am.Chem.Soc. 117. 7019-7020 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makkoto Sasaki: "Synthetic approach toward complete structure determination of maitotoxin. Stereochemical assignment the of C63-C68 acyclic linkages." Tetrahedron Lett. 36. 9007-9010 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Sasaki: "Stereochemical assignement of the C35-C39 acyclic likage in maitotoxin : completion of stereochemical determination of C15-C134" Tetrahdedron Lett. 36. 9011-9014 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Nobuaki Matsumori: "Long-range carbon-proton coupling constants for stereochemical assignment of acyclic structures in natural products : configuration of the C5-C9 portion of maitotoxin." Tetrahedron Lett.37. 1269-1272 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Sasaki: "Synthetic approach toward complete struiture determnation of maitotoxin" Tetrahedron Letters. 36. 9007-9010 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Makoto Sasaki: "Stcreochemical assignment of the C35-C39 acyclic Linhage in maitotoxin" Tetrahedron Letters. 36. 9011-9014 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Nobuaki Matsumori: "Conformational analysis of natural products using Long-range corbon-proton coupling constants" Tetrahedron. 51. 12229-12238 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Michio Murata: "Structure and Partial Stereochemical Assignments for Maitotoxin" Journal of American Chemical Society. 116. 7098-7107 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Makoto Sasaki: "Synthesis and Stereochemical Confirmation of the cis-Fused L/M.N/O Rings of Maitotoxin" Tetrahedron Letters. 35. 5023-5026 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 村田道雄: "分子量3422の海洋猛毒・マイトトキシンの構造" 有機合成化学協会誌. (印刷中). (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] 村田道雄: "天然有機化合物の構造解析" シュプリンガー・フェアラーク東京(伏谷、廣田 編), 326 (1994)

    • Related Report
      1994 Annual Research Report

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Published: 1994-04-01   Modified: 2016-04-21  

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