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Organic synthesis and Production based on Bioresources and Biocatalysis

Research Project

Project/Area Number 12660102
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  faculty of Science and Technology, Keio University, Associate Professor, 理工学部, 助教授 (60171120)

Project Period (FY) 2000 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2001: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2000: ¥2,200,000 (Direct Cost: ¥2,200,000)
KeywordsBiocatalysts / kinetic resolution / hydrolysis / reduction / functional group transformation / glycoconjugates / 光学活性カルボン酸 / リパーゼ / 速度論的光学分割 / ニトリルヒドラターゼ / エステラーゼ / シアノヒドリン / アミノ糖 / N-アセチルグルコサミン / Rhodococcus rhodochrous / パパイン
Research Abstract

A variety of methods and theory controlling the reaction species and conditions in organic chemistry has recently been developed. Enzymes are exception. Chemists look upon enzymes as elegant reagents in molecular transformation, and many efforts have been devoted on the utilization of enzymes and microorganisms in synthetic organic chemistry. 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 (2000-2001), moreover, the starting materials were secured from the new source, bio-mass and fermentation products.
The achievements were; 1) Synthesis of enantioemrically enriched compounds by anti-Prelog yeast (Yamadazyma farinosa)-catalyzed asymmetric reduction; 2) Asymmetrization and kinetic resolution by means of a yeast (Torulaspora delbrueckii) catalyzed reduction; 3) Clarification of some phenomena observed in lipase-catalyzed hydrolysis and esterification toward the establishment of efficient kinetic resolution; 4) application on the synthesis of glycoconjugates: N-acetylglucosaminyl-Cbz-asparagine; 5) Integrated combined process of chemo-enzymatic procedure: synthesis of (R)-2-naphthylmethoxyacetic acid.

Report

(3 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • Research Products

    (18 results)

All Other

All Publications (18 results)

  • [Publications] K.Fuhshuku, N.Funa, T.Akeboshi, H.Ohta, H.Hosomi, S.Ohta, T.Sugai: "The Access to Wieland-Miescher Ketone in an Enantio-merically Pure form by a Kinetic Rosolution with Yeast-mediated Reduction"J.Org.Chem.. 65. 129-135 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M.Suzuki, T.Yamazaki, H.Ohta, K.Shina, K., Ohi, S.Nishiyama, T.Sugai: "N-Carbamylamino Alcohols as the Precurson of Oxazolidinones via Nitrosation-deamination Roaction"Synlett. 189-192 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Yamazaki, A.Kuboki, H.Ohta, T.Milzel, L.A.Paquette, T.Sugai: "Yamadazyma farinosa IFO 10896-Mediated Reduction of 4,4-Dimethoxy-2-Butanone as the Key-Step for the Preparation of 1,3-Diols with Unsymmetrical Substituents"Synth.Commun.. 30. 3061-3072 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M.Suzuki, C.Nagasawa, T.Sugai: "Synthesis of Indanoxazolidinone based on the Lipase-catalyzed Resolution of the Corresponding N-Carbamylamino Derivative"Tetrahedron. 57. 4841-4848 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Akeboshi, Y.Ohtsuka, T.Ishihara, T.Sugai: "Chemo-enzymatic Approach foward the Pure Enantiomers of 2-Methyl-1,3-Propanediol Mono P-Methoxybenzyl Ether"Adv.Synth.Catal.. 343. 624-637 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y.Tokuda, Y.Takahashi, K.Matoishi, Y.Ito, T.Sugai: "Expeditious Route to GlcNAc-Cbz-Asn by Chemo-enzymatic Synthesis"Synlett. 57-60 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 鈴木麻珠三, 須貝 威: "キラル医薬・中間体のプロセス技術-開発・製造とアウトソーシングの動向(第三章第五節を分担執筆)"技術情報社. 182-208 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Fuhshuku, N. funa, T. Akeboshi, H. Ohta, H. Hosomi, S. Ohba, T. Sugai: "The Access to Wieland-Miescher Ketone in an Enantiomarically Pure Form by a Kinetic Resolution with Yeast-mediated Reduction"J. Org. Chem.. 65. 129-135 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] A. Kuboki, T. Ishihara, E. Kobayashi, H. Ohta, T. Ishii, A. Inoue, S. Mitsuda, T. Miyazaki, Y. Kajihara, T. Sugai: "Synthesis of Regioselectively Protected Forms of Cytidine Based on the enzyme-catalyzed Deacetylation as the Key Step"Biosci. Biotechnol. Biochem.. 64. 363-368 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Suzuki, T. Yamazaki, H. Ohta, K. Shima, K. Ohi, S. Nishiyama, T. Sugai: "N-Carbamylamino Alcohols as the Precursor of Oxazolidinones via Nitrosation-deamination Reaction"Synlett.. 189-192 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Yamazaki, A. Kuboki, H. Ohta, T. Mitzel. L.A. Paquette, T. Sugai: "Yamadazyma farinosa IFO 10896-Mediated Reduction of 4,4-Dimethoxy-2-butanone as The Key-Step for the Preparatation of 1,3-Diols With Unsymmetrical Substituents"Synth. Commun.. 30. 3061-3072 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Suzuki, C. Nagasawa, T. Sugai: "Synthesis of Indanoxazolidinone based on the Lipase-catalyzed Resolution of the Corresponding N-Carbamylamino derivative"Tetrahedron. 57. 4841-4848 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Akeboshi, Y. Ohtsuka, T. Ishihara, T. Sugai: "Chemo-enzymatic Approach toward the Pure Enantiomers of 2-Methyl-1,3-Propanediol Mono p-Methoxybenzyl Ether"Adv. Synth. Catal.. 343. 624-637 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y. Tokuda, Y. Takahashi, K. Matoishi, Y. Ito, T. Sugai: "Expeditious Route to GlcNAc-Cbz-Asn by Chemo-enzymatic Synthesis"Synlett. 57-60 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M.Suzuki, C.Nagasawa, T.Sugai: "Synthesis of Indanoxazolidinone based on the Lipase-catalyzed Resolution of the cornesponding N-carbonylamino Derivative"Tetrahedron. 57. 4841-4848 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Akeboshi, Y.Ohtsuka, T.Ishihara, T.Sugai: "Cheno-enzymatic Approach tpward Pure Enantiomers of 2-Methyl=1, 3-propanediol Mono p-Methoxybenzyl Ether"Adv.Synth.Catal.. 343. 624-637 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Y.Tokuda, Y.Takahashi, K.Matoishi, Y.Ito, T.Sugai: "Expedttious Route to GlcNAc-Cbz-Asn by chemo-enzymatic Synthesis"Synlett. 57-60 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Sugai, T.Kajimoto: ""Synthesis of Biologically Relevant Monosaccharides", in "Glycoscience-Chenstry and Chemical Biology""Springer-Verlag-GmbH. 907-1021 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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