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Screening of New Biocatalysts and Its Application to the Synthesis of Biologically Active Compounds

Research Project

Project/Area Number 09660120
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionDepatment of Chemistry, Keio University

Principal Investigator

SUGAI Takeshi  Keio University, Dept.of Chemistry Associate Professor, 理工学部, 助教授 (60171120)

Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 1998: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1997: ¥2,200,000 (Direct Cost: ¥2,200,000)
KeywordsAmino Alcohol / Ceramide / Lipase / Kinetic Resolution / Pheromone / Amino Sugar / Regioselective Acylation / フェリエ反応 / グリカ-ル / 位置選択的保護 / 〔3,3〕-シグマトロピー転位
Research Abstract

Results of screeing of new biocatalysts and its application to the synthesis of biologically active compounds are summalized as follows. 1) pivotal role of (E)-3-carbamoyl-1-propenylboronic acid in the combination of Suzuki-Miyaura coupling and enzyme reactions : synthesis of (3E,5E)- and (3E,5Z)-6-phenyl-3,5-hexadienoic Acid ; 2) biocatalyst-mediated efficient preparation of highly enantiomerically enriched (R)-5-hexanolide ; 3) A chemo-enzymatic synthesis of D-allosamine derivatives from Tri-O-acetyl-D-glucal ; 4) Rhodococcus rhodochrous IFO 15564-mediated hydrolysis of alicyclic nitriles and amides : its stereoselectivity, and the use for kinetic resolution and asymmetrization ; 5) lipase-catalyzed enantiomeric resolution of ceramides.

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (14 results)

All Other

All Publications (14 results)

  • [Publications] Sugai, T.et al.: "Pivotal Role of(E)--Carbamoyl-1-propenylboronic Acid in the Combination of Suzuki-Miyaura Coupling and Enzyme Reactions : Synthesis of (3E, 5E)- and (3E, 5Z)-6-Phenyl-3, 5-hexadienoic Acid" Chem.Lett.797-798 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Sugai, T.et al.: "Biocatalyst-mediated Efficient Preparation of Highly Enantiomerically Enriched(R)-5-Hexanolide" Synlett. 983-985 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Sugai, T.et al.: "Biocatalysis in Organic Synthesis : The Use of Nitrile- and Amide-Hydrolyzing Microorganisms" Biosci.Biotechnol.Biochem.61. 1419-1427 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Sugai, T.et al.: "A Chemo-enzymatic Synthesis of D-Allosamine Derivatives from Tri-O-acetyl-D-glucal" Bull.Chem.Soc., Jpn. 70. 2535-2540 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Sugai, T.et al.: "Rhodochrous rhodochrous IFO 15564-mediated Hydrolysis of Alicyclic Nitriles and Amides : Its Stereoselectivity, and the Use for Kinetic Resolution and Asymmetrization" Tetrahedron : Asymmetry. 9. 1097-1102 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Sugai, T.et al.: "Lipase-catalyzed Enantiomeric Resolution of Ceramides" J.Org.Chem.63. 6929-6938 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Sugai, T.et al.: "Pivotal Role of (E) --Carbamoyl-1-propenylboronic Acid in the Combination of Suzuki-Miyaura Coupling and Enzyme Reactions : Synthesis of (3E,5E) -and (3E,5Z) -6-Phenyl-3,5-hexadienoic Acid" Chem.Lett.797-798 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] "Biocatalyst-mediated Efficient Preparation of Highly Enantiomerically Enriched (R) -5-Hexanolide" Synlett. 983-985 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] "Biocatalysis in Organic Synthesis : The Use of Nitrile-and Amide-Hydrolyzing Microorganisms" Biosci.Biotechnol. 61 Biochem.1419-1427 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] "A Chemo-enzymatic Synthesis of D-Allosamine Derivatives from Tri-O-acetyl-D-glucal" Bull.Chem.Soc., Jpn.70. 2535-2540 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] "Rhodochrous rhodochrous IFO 15564-mediated Hydrolysis of Alicyclic Nitriles and Amides : Its Stereoselectivity, and the Use for Kinetic Resolution and Asymmetrization" Tetrahedron : Asymmetry. 9. 1097-1102 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] "Lipase-catalyzed Enantiomeric Resolution of Ceramides" J.Org.Chem.63. 6929-6938 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Sugai,T.et al.: "Lipase-catalyzed Enantiomeric Resolution of Ceramides" J.Org.Chem.63. 6929-6938 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Sugai,T.et al: "A Chemo-Enzymafic Synthesis of D-Allosamine Derivatlves from Tri-O-Acetyl-D-glucol" Bull.Chem.Soc.Jpn. 70. 2535-2540 (1997)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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