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Synthesis of biologically Active Compounds by Using Enzymatic Procedure

Research Project

Project/Area Number 61571005
Research Category

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

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

Principal Investigator

KIYOSHI Sakai  Kyushu University, 薬学部, 教授 (90153840)

Co-Investigator(Kenkyū-buntansha) HIROSHI Suemune  Kyushu University, 薬学部, 助手 (20095897)
KAZUHISA Funakoshi  Kyushu University, 薬学部, 助手 (50037579)
Project Period (FY) 1986 – 1987
Project Status Completed (Fiscal Year 1987)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1987: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1986: ¥1,600,000 (Direct Cost: ¥1,600,000)
KeywordsEnzymatic Hydrolysis / Microbial Reduction / Asymmetric Hydrolysis / Prostaglandins / Asymmetric Reduction / Platelet-Activating Factor / 生体中微量成分 / キラルシントン / カーバサイクリン / 環縮小反応
Research Abstract

Asymmetric syntheses of biologically active compounds such as prostaglandins (PGs) and platelet-activating factor (PAF) were studied by using enzymatic procedure.
1. Syntheses of optically active intermediates for carbacyclin, 11-deoxy-PGs, and PGA_2 were achieved by means of microbial reduction, asymmetric hydrolysis, and enantioselective hydrolysis, respectively.
2. Asymmetric syntheses of 2,3-O-isopropylidene-sn-glycerol and (-)-batyl alcohol, key synthetic intermediates for PAF, were achieved by enzymatic hydrolysis and microbial reduction.
3. (1) For preparation of optically active cyclopentane derivatives, enzymatic procedure was proved to be efficient in both kinetic resolution of racemic compounds and asymmetric induction of meso-compounds. As the result of our investigation, Pseudomonas fluorescens lipase was the most effective for above purpose.
(2) Chiral highly functionalized cyclopentanones were obtained by microbial reduction. Starting from the new chiral synthoh, (-)-<alpha>- and (+)-<beta>-Cuparenones, Cuparene, and Laurene were synthesized.

Report

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

    (22 results)

All Other

All Publications (22 results)

  • [Publications] Zhuo-Feng Xie: Chem.Pharm.Bull.34. 3058-3060 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroshi Suemune: Chem.Pharm.Bull.34. 3440-3444 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroshi Suemune: Chem.Pharm.Bull.35. 1741-1747 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroshi Suemune: Chem.Pharm.Bull.35. 3112-3118 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Zhuo-Feng Xie: J.Chem.Soc.,Chem.Commun.838-839 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Zhuo-Feng Xie: Chem.Pharm.Bull.35. 4454-4459 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroshi Suemune: Chem.Pharm.Bull.36. 15-21 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Kouji Okano: Chem.Pharm.Bull.36. (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Kouji Okano: Chem.Pharm.Bull.36. (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Zhuo-Feng Xie: "Using Microbial Reduction to Synthesize Carbacyclin" Chem. Pharm. Bull.34. 3058-3060 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroshi Suemune: "Enzymatic Synthesis of 2,3-O-Isopropylidene-sn-glycerol, a Chiral Building Block for Platelet-Activating Factor" Chem. Pharm. Bull.34. 3440-3444 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroshi Suemune: "Enzymatic Procedure for the Synthesis of 11-Deoxyprostaglandins" Chem. Pharmr. Bull.35. 1741-1747 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroshi Suemune: "Asymmetric Synthesis of (+)- and (-)-Batyl Alcohol, a Key Synthetic Intermediate for Platelet-Activating Factor, by Using Biocatalysts" Chem. Pharm. Bull.35. 3112-3118 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Zhuo-Feng Xie: "Enantioselective Hydrolysis of Five-membered-ring Acetates catalyzed Pseudomonas fluorescens Lipase" J. Chem. Soc., Chem. Commun.838-839 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Zhuo-Feng Xie: "Application of Microorganisms and Enzymes to the Synthesis of Chiral Cyclopentane and Bicyclo[3.3.0]octane Derivatives" Chem. Pharm. Bull.35. 4454-4459 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroshi Suemune: "Enzymatic Procedure for the Synthesis of Prostaglandin A_2" Chem. Pharm. Bull.36. 15-21 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Kounji Okano: "Preparation of Chiral Highly Functionalized Cyclopentanones" Chem. Pharm. Bull.36. in press (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Kouji Okano: "Formal Syntheses of (-)-<alpha>- and (+)-<beta>-Cuparenones,Cuparene, and Laurene" Chem. Pharm. Bull.36. in press (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Z,-F.Xie: Chem.Pharm.Bull.34. 3058-3060 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] H.Suemune: Chem.Pharm.Bull.34. 3440-3444 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] H.Suemune: Chem.Pharm.Bull.35. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] H.Suemune: Chem.Pharm.Bull.35. (1987)

    • Related Report
      1986 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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