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Bioorganically Chemical Studies on Abscisic Acid Analogs Produced by a Fungus.

Research Project

Project/Area Number 01560132
Research Category

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

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

ORITANI Takayuki  Tohoku University, Faculty of Agriculture, Associate Professor., 農学部, 助教授 (20005630)

Co-Investigator(Kenkyū-buntansha) YAMASHITA Kyohei  Tohoku University, Faculty of Agriculture, Professor., 農学部, 教授 (90005570)
Project Period (FY) 1989 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1990: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1989: ¥1,600,000 (Direct Cost: ¥1,600,000)
KeywordsAbscisic acid / Plant hormone / Hydroxy-gamma-ionylideneacetic acid / Fungal metabolite / Biological activity / 1',4'ージヒドロキシーγーイオニリデン酢酸 / 微生物代謝物 / 1',4'ジヒドロキシーγーイオニリデン酢酸 / 微生物代謝産物 / 4'-ひどろきし-γ-イオニリデン酢酸 / 1',4'-ジヒドロキシン-γ-イオニリデン酢酸
Research Abstract

1) (<plus-minus>)-4^' -hydroxy-gamma-ionylideneacetic acid ; a analog of abscisic acid (ABA) produced a fungus Cercospora cruenata, was synthesized from 3, 3, 5-trimethy1-4-cyclohexenyl acetate, which was prepared from isophorone.
2) A chiral synthone ; (S) -2, 2-dimethy1-4-hydroxy-1-cyclohexanone was prepared by yeast reduction of 1-ethyleneglycol. Acetal of (<plus-minus>) -2, 2-di menthy1-1, 4-cyclohexadione. Also, Microbial hydroxylation of 2, 2-dimethylcyclohexanone with Escherichia coli pJp43 gave the (S) -Ketol. sn2 reaction of the (S) -ketol by Mitsunobu method afforded the (R) -keto
3) Biosynthetic intermediates of ABA in C. cruenta ; natural 4^' -hydroxy- and 1^',4^' -dihydroxy- gamma-ionylideneacetic acid were synthesized from (R) -2, 2-dimethy1-4-hydroxy-1-cyclohexanone.
4) Plant physiological activities of ABA analogs produced by C. cruenta were examined. Also, Inhibitors of ABA biosynthesis in C. cruenta were selected. Synthesis and bioassay of 3^'-oxo analog of ABA were performed.

Report

(3 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] Takayuki Oritani: "Synthesis of (±)ー4'ーhydroxyーγーionylideneacetic acid,fungal biosynthotic intermediates of abscisisc acid" Agric.Biol.Chem.,. 54. 125-130 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Hiroshi Yamamoto: "Enzymatic preparation of chiral 4ーhydroxyー2,2ーdimethylー1ーCyclohexanone as chiral bailding block" Agric.Biol.Chem.,. 54. 1915-1921 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Hiroshi Yamamoto: "Synthesis of Chiral 4'ーhydroxy and 1',4'ーdihydroxyーγーionyideneacetic acid,fungal biosynthetic intermediates of adscisic acid" Agric.Biol.Chem.,. 54. 1923-1929 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] T. Oritani, H. Yamamoto and K. Yamashita: "Synthesis of (<plus-minus>)-4^'-hydroxy-gamma-ionylideneacetic acid fungal biosynthetic intermediates of abscisic acid." Agric. Biol. Chem.54. 125-130 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] H. Yamamoto, T. Oritani and K. Yamashita: "Enzymatic preparation of chiral 4-hydroxy-2, 2-dimethyl-1-cyclohexanone as chiral building block." Agric. Biol. Chem.54. 1915-1921 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] H. Yamamoto, T. Oritani and K. Yamashita: "Synthesis of chiral 4^'-hydroxy- and 1^'-dihydroxy-gamma-ionylideneacetic acid, fungal biosynthetic intermediates of abscisic acid." Agric. Biol. Chem.54. 1923-1929 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Takayuki Oritani: "Synthesis of(±)ー4'ーhydroxyーγーionylideneacetic acid,fungal biosynthetic intermediates of abscisic acid" Agric.Biol.Chem.,. 54. 125-130 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Hiroshi Yamamoto: "Enzymatic preparation of chiralー4ーhydroxyー2,2ーdimethylー1ーcyclohexanone as chiral building block" Agric.Biol.Chem.,. 54. 1915-1921 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Hiroshi Yamamoto: "Synthesis of chiral 4'ーhydroxy and 1',4'ーdihydroxyーγーionylideneacetic acid,fungal biosynthetic intermediates of abscisic acid." Agric.Biol.Chem.,. 54. 1923-1929 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Takayuki ORITANI: "Synthesis of(±)-4'-hydroxy-γ-ionylideneacetic acids,fungalbiosynthetic intermediates of abscisic acid." Agric.Biol.Chem.54. 125-130 (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Hiroshi YAMAMOTO: "Enzymic Preparation of Chiral 4'-hydroxy-2.2-dimethy1-1-cyclohexanone as chiral building block" Agric.Biol.Chem.,.

    • Related Report
      1989 Annual Research Report
  • [Publications] Hiroshi YAMAMOTO: "Synthesis of chiral 4'-hydroxy-and 1,4'-dihydroxhy-r-ionylideneacetic acids,fungal biosynthetic intermediates of abscisic acid.hi"

    • Related Report
      1989 Annual Research Report

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Published: 1989-04-01   Modified: 2016-04-21  

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