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Development of Microbial Enzymatic Catalysts towards the Chemo-Enzymatic Synthesis of Bioactive Substances

Research Project

Project/Area Number 14560084
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionKeio University

Principal Investigator

SUGAI Takeshi  Keio Univ., Faculty of Science and Technology, Associate Professor, 理工学部, 助教授 (60171120)

Project Period (FY) 2002 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2003: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2002: ¥2,200,000 (Direct Cost: ¥2,200,000)
KeywordsMicrobial Enzymes / Yeast-mediated Reduction / Natural Product Synthesis / Kinetic Resolution / Amino Acid / 加水分解酵素
Research Abstract

An important aspect in the enzyme-catalyzed production of chemicals is the complementary and synergistic use of chemo-enzymatic procedure so that we can draw a reasonable and straightforward blueprint towards the target molecules. Needless to say, a remarkable advantage is that enzymes are the catalysts whose supply from microorganisms, animals, and plants never quit, as the resources can be reproduced in a self-production manner.
In this study supported by the grant-in-aid (2002-2003), the achievements were ; 1) lipase-mediated kinetic resolution of heterocyclic amino acids including N-protected forms of proline and N-protected forms of indolinecarboxyolic acid ; 2) Asymmetrization of prochira diketones by means of a yeast (Torulaspora delbrueckii) catalyzed reduction to provide enantiomerically pure cyclic hemiacetals ; 3) Radical-mediated conversion of the cyclic acetals to α-alkenyl-substituted β-hydroxycyclohexanone, which would be the starting material of terpenoids such as tryptocallols and madindolines ; 4) substrate specificity study and long-term preservable cell preparation of the above new biocatalyt, Torulaspora delbrueckii ; 5) combination of electroorganic chemistry (constant current electrolysis) and enzyme-catalyzed desymmetrization of a prochiral diester to give the key intermediate of natural occurring bioactive product, such as helianulol E.

Report

(3 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • Research Products

    (17 results)

All Other

All Publications (17 results)

  • [Publications] M.Kimura, A.Kuboki, T.Sugai: "Chemo-enzymatic Synthesis of Enantiomerically Pure (R)-2-Naphthyl-methoxyacetic acid"Tetrahedron : Asymmetry. 13. 1059-1068 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Fuhshuku, T.Sugai: "Access to Enantiomerically Pure Intermediates of Geosmin Synthesis Starting from (4aS,8S)-4,4a,5,6,7,8-Hexahydro-4a,8-dimethylnaphthalen-2(3H)-one"Biosci.Biotechnol.Biochem.. 66. 2267-2272 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] F.Doi, T.Ogamino, T.Sugai, S.Nishiyama: "Enantioselective Synthesis of Helianulol E ; Structural Consideration of Natural Molecule"Tetrahedron Lett.. 44. 4877-4880 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kurokawa, T.Shindo, M.Suzuki, N.Nakajima, K.Ishihara, T.Sugai: "Enzyme-catalyzed Enantiomeric Resolution of N-Boc-proline as the Key-step in an Expeditious Route toward RAMP"Tetrahedron : Asymmetry. 14. 1323-1333 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Fuhshuku, M.Tomita, T.Sugai: "Enantiomerically Pure Octahydronaphthalenones and Octahydroindenone : Elaboration of Substrate Overcame the Specificity of Yeast-mediated Reduction"Adv.Synth.Catal.. 345. 766-774 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Fuhshuku, M.Tomita, T.Sugai: "Unprecedented Chemo-enzymatic Synthesis of Stereochemically Pure 3-Acetoxy-2-methyl-2-vinylcycloalkanones"Tetrahedron Lett.. 45. 1763-1767 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kimura, A.Kuboki, T.Sugai: "Chemo-enzymatic Synthesis of Enantiomerically Pure (R)-2-Naphthyl-methoxyacetic acid"Tetrahedron : Asymmetry. 13. 1059-1068 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Fuhshuku, T.Sugai: "Access to Enantiomerically Pure Intermediates of Geosmin Synthesis Starting from (4aS, 8S)-4,4a,5,6,7,8-Hexahydro-4a,8-dimethylnaphthalen-2(3H)-one"Biosci.Biotechnol.Biochem.. 66. 2267-2272 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] F.Doi, T.Ogamino, T.Sugai, S.Nishiyama: "Enantioselective Synthesis of Helianulol E ; Structural Consideration of Natural Molecule"Tetrahedron Lett.. 44. 4877-4880 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kurokawa, T.Shindo, M.Suzuki, N.Nakajima, K.Ishihara, T.Sugai: "Enzyme-catalyzed Enantiomeric Resolution of N-Boc-proline as the Key-step in an Expeditious Route toward RAMP"Tetrahedron : Asymmetry. 14. 1323-1333 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Fuhshuku, M.Tomita, T.Sugai: "Enantiomerically Pure Octahydronaphthalenones and Octahydroindenone : Elaboration of Substrate Overcame the Specificity of Yeast-mediated Reduction"Adv.Synth.Catal.. 345. 766-774 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Fuhshuku, M.Tomita, T.Sugai: "Unprecedented Chemo-enzymatic Synthesis of Stereochemically Pure 3-Acetoxy-2-methyl-2-vinylcycloalkanones"Tetrahedron Lett.. 45. 1763-1767 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kurokawa, T.Shindo, M.Suzuki, N.Nakajima, K.Ishihara, T.Sugai: "Enzyme-catalyzed Enantiomeric Resolution of N-Boc-proline as the Key-step in an Expeditious Route toward RAMP"Tetrahedron : Asymmetry. 14. 1323-1333 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Fuhshuku, M.Tomita, T.Sugai: "Enantiomerically Pure Octahydronaphthalenones and Octahydroindenone : Elaboration of Substrate Overcame the Specificity of Yeast-mediated Reduction"Adv.Synth.Catal.. 345. 766-774 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Fuhshuku, M.Tomita, T.Sugai: "Unprecedented Chemo-enzymatic Synthesis of Stereochemically Pure 3-Acetoxy-2-methyl-2-vinylcycloalkanones"Tetrahedron Lett.. 45. 1763-1767 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Kimura, A.Kuboki, T.Sugai: "Chemo-enzymatic Synthesis of Enantiomerically Pure (R)-2-Naphthylmethoxyacetic acid"Tetrahedron : Asymmetry. 13. 1059-1068 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Fuhshuku, T.Sugai: "Access to Enantiomerically Pure Intermediates of Geosmin Synthesis Starting from (4aS, 8S)-4, 4a, 5, 6, 7, 8-Hexahydro-4a, 8-dimethylnaphthalen-2(3H)-one"Biosci. Biotechnol. Biochem. 66. 2267-2272 (2002)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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