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Asymmetric Synthesis of Pheromones by the Use of Immobilized Biocatalysts in Organic Solvent Systems

Research Project

Project/Area Number 63560135
Research Category

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

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionOkayama University of Science

Principal Investigator

NAOSHIMA Yoshinobu  Okayama University of Science, Faculty of Science, Department of Biological Chemistry, Associate Professor, 理学部, 助教授 (20113194)

Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1989: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1988: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsBiocatalysts / Immobilized Biocatalysts / Baker's Yeast / Lipases / Plant Cell Cultures / Biotransformation / Pheromones / Asymmetric Synthesis / 生化学的交換 / 生物変換 / 生体触媒を利用する有機合成 / 固定化パン酵母 / 固定化リパーゼ / 固定化植物培養細胞
Research Abstract

1. Immobilized baker's yeast entrapped in calcium alginate beads of 1-1.5 mm diameter was reusable more than 10 times and stereoselectively reduced ethyl 3- oxobutanoate to the corresponding (S)-hydroxy ester in high chemical and optical yields. The biocatalyst was also active in organic solvent systems including hexane and similarly reduced the keto ester in a high optical yield of 95% ee.
2. Immobilized cells of Nicotiana tabacum entrapped in calcium alginate beads were reusable several times and transformed four different 3-oxobutanoates to the corresponding hydroxy esters in reasonable chemical yields and relatively high optical yields. The consecutive reuse of the immobilized cells enhanced the rates of the biotransformations. The time-course experiments of the biotransformations revealed that the rates of the transformations of 3-oxobutanoates, which have longer n-alkyl chains in their alkoxycarbonyl groups, were higher than those of homologs possessing shorter alkyl chains.
3. Asymmetric synthesis of some pheromones was done employing biotransformation with immobilized biocatalysts such as baker's yeast and lipases entrapped in calcium alginate or glass beads. Both the enantiomers of phoracantholide I (defensive secretion of Phoracantha synonyms), (5Z,13S)-5-tetradecen-13-olide (aggregation pheromone of Cryptolestes grain beetle), (2R,8R)-8-methyl-2-decanol propionate (sex pheromone of some Diabrotica species), and two stereoisomers of 6,10,14-trimethyl-2-pentadecanol (sex pheromone of Corcyra cephalonica Stainton) were therefore synthesized in high optical yields, respectively.

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (24 results)

All Other

All Publications (24 results)

  • [Publications] Yoshinobu Naoshima: "固定化生体触媒によるフェロモン類の不斉合成" Bio Industry. 6. 127-133 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoshinobu Naoshima: "Biotransformation of Acetoacetic Esters with Immobilized Cells of Nicotiana tabacum" Agric.Biol.Chem.53. 545-547 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoshinobu Naoshima: "Synthesis of Both the Enantiomers of Phoracantholide I,A Defensive Secretion of the Eucarypt Longicorn(Phoracantha synonyma),Employing Microbial Asymmetric Reduction with Immobilized Baker's Yeast" Bull.Chem.Soc.Jpn.62. 608-610 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoshinobu Naoshima: "Asymmetric Bioreduction of Ethyl 3-Oxobutanoate by Immobilized Baker's Yeast Entrapped in Calcium Alginate Beads.Application of the Immobilized Biocatalyst to the Synthesis of(5z,13S)-5-Tetra-decen-13-olide,Aggregation Pheromone of Cryptolestes Grain Beetle" Chem.Lett.1023-1026 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoshinobu Naoshima: "Bioreduction of Ethyl 3-Oxobutanoate with Immobilized Baker's Yeast in Organic-Water Solvent Systems" Chem.Lett.1517-1519 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoshinobu Naoshima: "Biotransformation of Some Keto Esters through the Consecutive Reuse of Immobilized Nicotiana tabacum Cells" J.Org.Chem.54. 4237-4239 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoshinobu Naoshima: "Synthesis of(5Z,13S)-5-Tetradecen-13-olide,Aggregation Pheromone of Cryptolestes Grain Beetle,Employing Asymmetric Bioreduction with Immobilized Baker's Yeast Entrapped in Calcium Alginate Beads" Bull.Chem.Soc.Jpn.(1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoshinobu Naoshima: "Asymmetric Synthesis of Pheromones by the use of Immobilized Biocatalysts." Bio Industry, 6, 127-133 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoshinobu Naoshima: "Biotransformation of Acetoacetic Esters with Immobilized Cells of Nicotiana tabacum." Agric. Biol. Chem., 53, 545-547 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoshinobu Naoshima: "Synthesis of Both the Enantiomers of Phoracantholide I, A Defensive Secretion of the Eucarypt Longicorn (Phoracantha synonyma), Employing Microbial Asymmetric Reduction with Immobilized Baker's Yeast." Bull. Chem. Soc. Jpn., 62, 608-610 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoshinobu Naoshima: "Asymmetric Bioreduction of Ethyl 3-Oxobutanoate by Immobilized Baker's Yeast Entrapped in Calcium Alginate Beads. Application of the Immobilized Biocatalyst to the Synthesis of (5Z, 13S)-5-Tetradecen-13-olide, Aggregation Pheromone of Cryptolestes Grain Beetle." Chem. Lett., 1023-1026 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoshinobu Naoshima: "Bioreduction of Ethyl 3-Oxobutanoate with Immobilized Baker's Yeast in Organic-Water Solvent Systems." Chem. Lett., 1517-1519 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoshinobu Naoshima: "Biotransformation of Some Keto Esters through the Consecutive Reuse of Immobilized Nicotiana tabacum Cells." J. Org. Chem., 54, 4237-4239 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoshinobu Naoshima: "Synthesis of (5Z, 13S)-5-Tetradecen-13-olide, Aggregation Pheromone of Cryptolestes Grain Beetle, Employing Asymmetric Bioreduction with Immobilized Baker's Yeast Entrapped in Calcium Alginate Beads." Bull. Chem. Soc. Jpn., 1990.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoshinobu Naohima: "固定化生体触媒によるフェロモン類の不斉合成" Bio Industry. 6. 127-133 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Yoshinobu Naoshima: "Biotransformation of Acetoacetic Esters with Immobilized Cells of Nicotiana tabacum" Agric.Biol.Chem.53. 545-547 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Yoshinobu Naoshima: "Synthesis of Both the Enantiomers of Phoracantholide I,A Defenseve Secretion of the eucarypt Longicorn(Phoracantha synonyma),Employing Microbial Asymmetric Reduction with Immobilized Baker's Yeast" Bull.Chem.Soc.Jpn.62. 608-610 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Yoshinobu Naoshima: "Asymmetric Bioreduction of Ethy1 3-Oxobutanoate by Immobilized Baker's Yeast Entrapped in Calcium Alginate Beads.Application of the Immobilized Biocatalyst to the Synthesis of(5z,13s)-5-Tetradecen-13ーolide,Aggregation Pheromone of Cryptolestes Grain Beetle" Chem.Lett.1023-1026 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Yoshinobu Naoshima: "Bioreduction of Ethyl 3-Oxobutanoate with Immobilized Baker's Yeast in Organic-Water Solvent Systems" Chem.Lett.1517-1519 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Yoshinobu Naoshima: "Biotransformation of Some Keto Esters through the Consecutive Reuse of Immobilized Nicotiana tabacum Cells" J.Org.Chem.54. 4237-4239 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Yoshinobu Naoshima: "Synthesis of(5z,13s)-5-Tetradecen-13-olide,Aggregation Pheromone of Cryptolestes Grain Beetle,Employing Asymmetric Bioreduction with Immobilized Baker's Yeast Entrapped in Calcium Alginate Beads" Bull.Chem.Soc.Jpn.(1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Yoshinobu Naoshima: Bull.Chem.Soc.Jpn.62. 608-610 (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] 直島好伸: BIO INDUSTRY(バイオ・インダストリー). 6. 127-133 (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] Yoshinobu Naoshima: Agric.Biol.Chem.53. inpress (1989)

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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