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Asymmetric Synthesis of Optically Active Natural Products by Lipase-Catalyzed Hydrolysis in Organic Solvent System

Research Project

Project/Area Number 06660139
Research Category

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

Allocation TypeSingle-year Grants
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionOkayama University of Science

Principal Investigator

NAOSHIMA Yoshinobu  Okayama University of Science, Fuaculty of Scuebcem Department of Biochemistry Professor, 理学部, 教授 (20113194)

Project Period (FY) 1994 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1995: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1994: ¥1,300,000 (Direct Cost: ¥1,300,000)
KeywordsBiocatalyst / Lipase / Bioransformation / Enantioselectivity / Pheromone / Hydrolysis / Asymmetric Synthesis / Enzymatic Reaction / フエロモン / 光学活性天然物
Research Abstract

1. We showed that lipase PS-catalyzed hydrolysis displays a higher enantioselectivity in an acetone-water system than in an aqueous system and that the biocatalytic system conyaining acetone could be successfully applied to the chiral synthesis of both the enantiomers of 3-octanol, the pheromone of various species of ants, of (S) 2-tridecanyl acetate and (S) -2-pentadecanyl acetate, the aggregation pheromone components of Drosophila mulleri and D.busckii, and of (R) patulolide A,a macrolide antibiotic isolated from Penicillium urticae S11R59.
2. We carried out the enzymatic hydrolysis of the acetates of aliphatic secondary alcohols with lipases PS,AK,and LIP.High enantioselectivity was observed for the lipase PS-catalyzed hydrolysis of (E) -allylic acetate and propargylic acetate in an acetone-water solvent system. In contrast, a decrease in enantio-selectivity was observed for (E) -homoallylic acetate and homopropargylic acetate. The enantioselectivity of lipase LIP (Pseudomonas sp.) was different from that of lipases PS and AK (Pseudomonas sp.).

Report

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

    (15 results)

All Other

All Publications (15 results)

  • [Publications] Makoto Kamezawa: "Preparation of Both the Enantiomers of 3-Octanol,the Pheromone of Various Species of Ants,by Enantioselective Hydrolysis" Biosci. Biotech. Biochem.58. 598-599 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Kamezawa: "Biocatalytic Synthesis of (S)-2-Tridecanyl Acetate and (S)-2-Pentadecanyl Acetate" J. Chem. Ecol.20. 1057-1061 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Kamezawa: "Enzymatic Hydrolysis of Alken-and Alkyn-3-ol Acetates in an Acetone-Water Solvent System" Biosci. Biotech. Biochem.59. 549-551 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Kamezawa: "Chemoenzymatic Synthesis of (R)-(+)-Patulolide A,a Macrolide Antibiotic Isolated from Penicillium" Liebigs Ann. Chem.(in press). (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Kamezawa: "Preparation of Both the Enantiomers of 3-Octanol, the Pheromone of Various Species of Ants, by Enantioselective Hydrolysis with Pseudomonas cepacia Lipase" Biosci.Biotech.Biochem.58. 598-599 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Kamezawa: "Biocatalytic Synthesis of (S) -2-Tridecanyl Acetate and (S) -2-Pentadecanyl Acetate, Aggregatio Pheromone Components of Drosophila mulleri and D.busckii, by Enantioselective Hydrolysis with Lipase" J.Chem.Ecol.20. 1057-1061 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Kamezawa: "Enzymatic Hydrolysis of Alken- and Alkyn-3-ol Acetate in an Acetone-Water Solvent System : Effect of Unsaturation on the Enantioselectivity of Pseudomonas cepacia Lipase-catalyzed Hydrolysis" Biosci.Biotech.Biochem.59. 549-551 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Kamezawa: "Chemoenzymatic Synthesis of (R) - (+) -Patulolide A,a Macrolide Antibiotic Isolated from Penicillium urticae" Liebigs Ann.Chem.(in press). (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Makoto Kamezawa: "Proparation of Both the Enantiomers of 3-Octanol, the Pheromone of Various Species of Ants, by Enatioselective Hydrolysis" Biosci. Biotech. Biochem.58. 598-599 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] Makoto Kamezawa: "Biocatalytic Synthesis of (S)-2-Tridecanyl Acetate and (S)-2-Pentadecanyl Acetate" J. Chem. Ecol.20. 1057-1061 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] Makoto Kamezawa: "Enzymatic Hydrolysis of Alken-and Alkyn-3-ol Acetates in an an Acetone-Water Solvent System" Biosci. Biotech. Biochem.59. 549-551 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Makoto Kamezawa: "Chemoenzymatic Synthesis of (R)-(+)-Patulolide A, a Macrolide Antibiotic Isolated from Penicillium urticae" Liebigs Ann. Chem.(in press). (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Makoto Kamezawa: "Prearation of Both the Enartiamers of 3-Octard,the Pheromonc of Various Species of Ants,by Enantioselective Hydrolysis wth Pscudomonos cepacia Lipasc" Btosci.Biotech.Biochem.58. 598-599 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Makoto Kamezawa: "Biocatalytic Synthesis of (S)-2-Tridecanyl Acetate and (S)-2-Pentadecanyl Acetate" J.Chem Ecol.20. 1057-1061 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Makoto Kamezawa: "Enzymatic Hydrolysis of Alken-and Alkyn-3-ol Azetates in an Acetone-lvater Solvent System" Btosci.Biotech.Biochem.in press.

    • Related Report
      1994 Annual Research Report

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

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