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Synthesis of the Host-specific Toxins, AK- and AF-toxin

Research Project

Project/Area Number 61571007
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionNagasaki University

Principal Investigator

IRIE Hiroshi  Professor, Nagasaki University, 薬学部, 教授 (00025686)

Co-Investigator(Kenkyū-buntansha) UENO Tamio  Associate Professor, Kyoto University, 農学部, 助教授 (20026579)
TAKEDA Sigeko  Research Assistant, Nagasaki University, 薬学部, 助手 (50039640)
Project Period (FY) 1986 – 1987
Project Status Completed (Fiscal Year 1987)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1987: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1986: ¥1,200,000 (Direct Cost: ¥1,200,000)
KeywordsTotal synthesis of natural products / Host-specific toxins / Nijisseiki / Stereostructure / 不斉源 / 植物病原菌 / 宿主特異的毒性 / 二十世紀黒斑病 / 全合成 / 不斉合成原料としてのビタミン C
Research Abstract

Total synthesis of the methyl esters of AK-toxin II and AF-toxin IIa and IIc, the host-specific toxins for Japanease pear Nijisseiki, was accomplished by starting from Vitamin C as a chiral starting material. Investigation of biological activities of several kinds of the intermediates prepared on the course of the synthesis confirmed that the stereochemistry of two chiral centers in the trienoic acid moiety of these toxins has tight relationship with toxic properties of the toxins. Futhermore, the synthesis revealed the availability of Vitamin C to synthesis of natural products as an appropriate chiral pool.

Report

(2 results)
  • 1987 Final Research Report Summary
  • 1986 Annual Research Report

Research Products

(7 results)

All Other

All Publications (7 results)

  • [Publications] 入江寛: Chemical & Pharmaceutical Bulletin. 34. 2668-2671 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 入江寛: Chemical & Pharmaceutical Bulletin. 35. 2598-2601 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroshi Irie, Kohei Matsumoto, and Yong Zhang: "Synthesis of the Host-specific Toxins AF-toxin IIc and AK-toxin Congeners and their Stereostructure-Toxicity Relationship" Chemical & Pharmaceutical Bulletin. 34. 2668-2671 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroshi Irie, Kohei Matsumoto, Takao Kitagawa, Yong Zhang, Tamio Ueno, Tadakazu Nakashima, and Hiroshi Fukami: "Total Synthesis of Esters of AK-toxin II and AF-toxin IIc Starting from Vitamin C as a Chiral Material" Chemical & Pharmaceutical Bulletin. 35. 2598-2601 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroshi Irie: Chemical & Pharmaceutical Bulletin. 33. 1313-1315 (1985)

    • Related Report
      1986 Annual Research Report
  • [Publications] Hiroshi Irie: Chemical & Pharmaceutical Bulletin. 34. 2668-2671 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Yong Zhang: Tetrahedron Letters.

    • Related Report
      1986 Annual Research Report

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Published: 1987-03-30   Modified: 2016-04-21  

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