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Chemo-enzymatic Synthesis of Biologically Active Compounds based on Biocatalysts and Bioresources

Research Project

Project/Area Number 16580092
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 University, Faculty of Science and Technology, Associate Professor, 理工学部, 助教授 (60171120)

Project Period (FY) 2004 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,900,000)
Fiscal Year 2005: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 2004: ¥2,400,000 (Direct Cost: ¥2,400,000)
Keywordsmicrobial enzymes / yeast reduction / natural product synthesis / kinetic resolution / amino acids / 生物資源 / 環境受容型反応
Research Abstract

Based on the chemo-enzymatic synthesis with complementary use of organic synthesis and enzyme-catalyzed transformation, the following researches were accomplished. 1) synthesis of heterocyclic amino acid containing proline, indoline-2-carboxylic acid, azetidine-2-carboxylic acid in enantiomerically pure forms. ; 2) synthesis of new building blocks for terpenoid synthesis, with a definite absolute stereochemistry in regard to quaternary carbon chiral center, by means of newly found yeast-catalyzed reduction of symmetrical cyclic diketones ; 3) nitrile hydratase and amidase originated from Rhodococcus rhodochrous-mediated transformation of prochiral nitriles into enantiomerically pure amide-carboxylate, and the transformation to α-methylamino acids.

Report

(3 results)
  • 2005 Annual Research Report   Final Research Report Summary
  • 2004 Annual Research Report
  • Research Products

    (15 results)

All 2005 2004

All Journal Article (15 results)

  • [Journal Article] The Short-step and Scalable Synthesis of (±)-Cytoxazone2005

    • Author(s)
      M.Asano, C.Nagasawa, M.Suzuki, S.Nishiyama, T.Sugai
    • Journal Title

      Biosci. Biotechnol. Biochem 69

      Pages: 145-148

    • NAID

      130000030565

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Chemo-enzymatic Short-step Total Synthesis of Symbioramide2005

    • Author(s)
      T.Takanami, H.Tokoro, D.Kato, S.Nishiyama, T.Sugai
    • Journal Title

      Tetrahedron Lett. 46

      Pages: 3291-3295

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Annual Research Report 2005 Final Research Report Summary
  • [Journal Article] Chemo-enzymatic Route to Both Enantiomers of 1-Isopropyl-3a-methyloctahydroinden-4-one Derivative, a Synthetic Intermediate for Sesqui- and Diterpenoids2005

    • Author(s)
      S.Fujieda, M.Tomita, K.Fuhshuku, S.Ohba, S.Nishiyama, T.Sugai
    • Journal Title

      Adv. Synth. Catal. 347

      Pages: 1099-1109

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] An Efficient Route to (S)-Azetidine-2-carbozylic Acid2005

    • Author(s)
      Y.Futamura, M.Kurokawa, R.Obata, S.Nishiyama, T.Sugai
    • Journal Title

      Biosci. Biotechnol. Biochem 69

      Pages: 1892-1987

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] 生命分子の変化をつかさどるタンパク触媒-酵素-触媒のしくみ,鏡像異性とのかかわりから物質合成まで2005

    • Author(s)
      須貝 威, 浅野正義
    • Journal Title

      化学と教育 53

      Pages: 436-439

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] An Efficient Route to (S)-Azetidine-2-carboxylic Acid2005

    • Author(s)
      Y.Futamura, M.Kurokawa, R.Obata, S.Nishiyama, T.Sugai
    • Journal Title

      Biosci.Biotechnol.Biochem. 69

      Pages: 1892-1987

    • NAID

      130000030520

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Chemo-enzymatic Route to Both Enantiomers of 1-Isopropyl-3a-methyloctahydroinden-4-one Derivative, a Synthetic Intermediate for Sesqui- and Diterpenoids2005

    • Author(s)
      S.Fujieda, M.Tomita, K.Fuhshuku, S.Ohba, S.Nishiyama, T.Sugai
    • Journal Title

      Adv.Synth.Catal. 347

      Pages: 1099-1109

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Annual Research Report 2005 Final Research Report Summary
  • [Journal Article] An Efficient Route to (S)-Azetidine-2-carboxylic Acid.2005

    • Author(s)
      Y.Futamura, M.Kurokawa, R.Obata, S.Nishiyama, T.Sugai
    • Journal Title

      Biosci.Biotechnol.Biochem 69

      Pages: 1892-1987

    • NAID

      130000030520

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 生命分子の変化をつかさどるタンパク触媒-酵素-触媒のしくみ、鏡像異性とのかかわりから物質合成まで2005

    • Author(s)
      須貝 威, 浅野正義
    • Journal Title

      化学と教育 53

      Pages: 436-439

    • Related Report
      2005 Annual Research Report
  • [Journal Article] The Short-step and Scalable Synthesis of (±)-Cytoxazone2005

    • Author(s)
      M.Asano, C.Nagasawa, M.Suzuki, S.Nishiyama, T.Sugai
    • Journal Title

      Biosci.Biotechnol.Biochem 69

      Pages: 145-148

    • NAID

      130000030565

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Mechanistic Studies on Nitrosation-deaminocyclization of Mono-carbamylated Vicinal Amino Alcohols and Diols : A New Preparative in situ Formation of Ethanediazoic Acid for the Ethylation of Carboxylate under Mild Conditions2004

    • Author(s)
      M.Suzuki, T.Sugai
    • Journal Title

      Bull. Chem. Soc. Jpn 77

      Pages: 1217-1227

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Both Enantiomers of N-Boc-indoline-2-carboxylic Esters2004

    • Author(s)
      M.Kurokawa, T.Sugai
    • Journal Title

      Bull.Chem.Soc.Jpn. 77

      Pages: 1021-1025

    • NAID

      10012940880

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A Control of the Nitrile-hydrolyzing Enzyme Activity in Rhodococcus rhodochrous IFO 15564 ; Preferential Action of Nitrile Hydratase and Amidase Depending on the Reaction Condition Factors and its Application to the One-pot Preparation of Amides from Aldehydes2004

    • Author(s)
      M.Kashiwagi, K.Fuhshuku, T.Sugai
    • Journal Title

      J.Mol.Catal.Sect.B enzymatic 29

      Pages: 249-258

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Realization of the Synthesis of α,α-Disubstituted Carbamylacetates and Cyanoacetates Either by Chemical or Enzymatic Functional Group Transformation, Depending upon the Substrate Specificity of Rhodococcus amidase2004

    • Author(s)
      M.Yokoyama, M.Kashiwagi, M.Iwasaki, K.Fuhshuku, H.Ohta, T.Sugai
    • Journal Title

      Tetrahedron : Asymmetry 15

      Pages: 2817-2820

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Mechanistic Studies on Nitrosation-deaminocyclization of Mono-carbamylated Vicinal Amino Alcohols and Diols : A New Preparative in situ Formation of Ethanediazoic Acid for the Ethylation of Carboxylate under Mild Conditions2004

    • Author(s)
      M.Suzuki, T.Sugai
    • Journal Title

      Bull.Chem.Soc.Jpn 77

      Pages: 1217-1227

    • Related Report
      2004 Annual Research Report

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Published: 2004-04-01   Modified: 2016-04-21  

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