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Design and synthesis of highly efficient substrate compatible to chemo-enzymatic synthesis

Research Project

Project/Area Number 23580152
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionKeio University

Principal Investigator

SUGAI Takeshi  慶應義塾大学, 薬学部, 教授 (60171120)

Project Period (FY) 2011 – 2013
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2013: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2012: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2011: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords有機化学 / 酵素合成 / 糖質化学 / 応用微生物学
Research Abstract

Under these circumstances that biocatalytic transformation is widely used, two approaches, the elaboration of "substrate molecular technology" and "quest of biocatalysts" should be emphasized. The aim of this approach is to find the optimized structure and synthetic routes of substrates, which would be maximally advantageous for both selectivity of enzyme-catalyzed reaction, and the total efficiency to target molecules. As the results through the research, three topics were achieved: 1) the exploration of the structure of alpha-haloketones which would be highly and efficiently reduced by stereoselective whole-cell microorganisms; 2) development of the structure of sugar oxazolines and glycal derivatives which serves free functional groups requisite for regio- and stereoselective transformation such as Ferrier reaction, were established. Based on them, new routes for (R)-terbutaline hydrochloride and rare sugars became available.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (16 results)

All 2014 2013 2012 2011 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results) Presentation (7 results) (of which Invited: 2 results)

  • [Journal Article] (-)-Benzyl 2,3-dideoxy-β-D-erythro-hex-2-enopyranoside2014

    • Author(s)
      S. Ohba, H. Okazaki, Y. Ueda, K. Hanaya, T. Sugai
    • Journal Title

      Acta Cryst. Sect. E

      Volume: E69 Issue: 12 Pages: o1811-o1811

    • DOI

      10.1107/s1600536813031140

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Towards the Integrated Exploitation of Microbial and Enzymatic Catalysis — Importance of Substrate Molecular Technology and Quest of Biocatalysts, for Designing Synthetic Plans2013

    • Author(s)
      古田未有、花屋賢悟、庄司満、須貝威
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 71 Issue: 3 Pages: 237-246

    • DOI

      10.5059/yukigoseikyokaishi.71.237

    • NAID

      10031157230

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chemo-enzymatic transformation of naturally abundant naringin to luteolin, a flavonoid with various biological effects2013

    • Author(s)
      R. Kobayashi, T. Itou, K. Hanaya, M. Shoji, N. Hada, T. Sugai
    • Journal Title

      J. Mol. Catal. B : Enz

      Volume: 92 Pages: 14-18

    • DOI

      10.1016/j.molcatb.2013.03.002

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of (R)-bambuterol based on asymmetric reduction of 1-[3,5-bis(dimethylcarbamoyloxy)phenyl]-2- chloroethanone with incubated whole cells of Williopsis californica JCM 36002013

    • Author(s)
      K. Asami, T. Machida, S. Jung, K. Hanaya, M. Shoji, T. Sugai
    • Journal Title

      J. Mol. Catal. B : Enz

      Volume: 97 Pages: 106-109

    • DOI

      10.1016/j.molcatb.2013.08.003

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Whole-cell yeast-mediated preparation of (R)-2-chloro-1-(3-nitro phenyl)ethanol as a synthetic precursor for (R)-phenylephrine2013

    • Author(s)
      D. Tokoshima, K. Hanaya, M. Shoji, T. Sugai
    • Journal Title

      J. Mol. Catal. B : Enz

      Volume: 97 Pages: 95-99

    • DOI

      10.1016/j.molcatb.2013.07.021

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] An expeditious route for 2-acetamido-4-O-methyl-2-deoxy-D-mannopyranose from a Ferrier derivative of tri-O-acetyl-D-glucal, which contributes to the synthesis of laninamivir (CS-8958), a neuraminidase inhibitor2013

    • Author(s)
      H. Okazaki, K. Hanaya, M. Shoji, T. Sugai
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 37 Pages: 7931-7935

    • DOI

      10.1016/j.tet.2013.07.018

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Chemo-Enzymatic Expeditious Route to Racemic Dihexanoyl (2<i>R</i>*,3<i>R</i>*,4<i>R</i>*)-Dehydroxymethylepoxyquinomycin (DHMEQ), the Precursor for Lipase-Catalyzed Synthesis of the Potent Nuclear Factor-&#954;B Inhibitor, (2<i>S</i>,3<i>S</i>,4<i>S</i>)-DHMEQ2012

    • Author(s)
      R. Kobayashi, K. Hanaya, M. Shoji, K. Umezawa, T. Sugai
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 60 Issue: 9 Pages: 1220-1223

    • DOI

      10.1248/cpb.c12-00417

    • NAID

      130001852541

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chemo-enzymatic routes for (R)-terbutaline hydrochloride based on microbial asymmetric reduction of a-haloacetophenones2012

    • Author(s)
      S. Taketomi, M. Asano, T. Higashi, M. Shoji and T. Sugai
    • Journal Title

      J. Mol. Catal. B: Enz.

      Volume: 84 Pages: 83-88

    • DOI

      10.1016/j.molcatb.2012.01.020

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Chemoenzymatic synthesis of (2R,3R,4R)-dehydroxymethylepoxyquinomicin (DHMEQ), a new activator of antioxidant transcription factor Nrf22011

    • Author(s)
      Y. Niitsu, M. Hakamata, Y. Goto, T. Higashi, M. Shoji, T. Sugai and K Umezawa
    • Journal Title

      Organic & Biomolecule Chemistry

      Volume: 9 Issue: 12 Pages: 4635-4641

    • DOI

      10.1039/c1ob05205e

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] β-選択的Ferrier反応を鍵段階とする、L-グルコースの合成研究2014

    • Author(s)
      岡崎隼人、植田裕二、大場茂、羽田紀康、花屋賢悟、庄司満、須貝威
    • Organizer
      日本化学会大94春季年会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-03-28
    • Related Report
      2013 Final Research Report
  • [Presentation] つねに再生・進化する酵素・バイオ触媒~ファインケミカル合成における活用2012

    • Author(s)
      須貝威
    • Organizer
      第二回CSJ化学フェスタ2012
    • Place of Presentation
      東京工業大学
    • Year and Date
      2012-10-16
    • Related Report
      2013 Final Research Report
  • [Presentation] The complementary and integrated chemo-enzymatic processes for fine chemical syntheses2012

    • Author(s)
      T. Sugai, Y. Yamashita, Y. Niitsu, M.Hamada, C. Hiraoka, T. Higashi, M. Shoji
    • Organizer
      APCChE2012
    • Place of Presentation
      Singapore
    • Year and Date
      2012-02-23
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] つねに再生・進化する酵素・バイオ触媒~ファインケミカル合成における活用2012

    • Author(s)
      須貝 威
    • Organizer
      第2回CSJ化学フェスタ2012
    • Place of Presentation
      東京工業大学 大岡山キャンパス
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] The Complementary and Integrated Chemo-enzymatic Processes for Fine Chemical Syntheses2012

    • Author(s)
      T. Sugai, Y. Yamashita, Y. Niitsu, M. Hamada, C. Hiraoka, T. Higashi, and M. Shoji
    • Organizer
      APCChE2012(招待講演)
    • Place of Presentation
      Singapore
    • Related Report
      2011 Research-status Report
  • [Presentation] トリアセチルD-グルカールから出発する4-O-メチル-ManNAcの合成研究

    • Author(s)
      岡崎隼人、花屋賢悟、庄司 満、羽田紀康、須貝 威
    • Organizer
      第32 回 日本糖質学会年会
    • Place of Presentation
      大阪国際交流センター
    • Related Report
      2013 Annual Research Report
  • [Presentation] β-選択的 Ferrier反応を鍵段階とする、L-グルコースの合成研究

    • Author(s)
      岡崎 隼人、植田 裕二、大場 茂、羽田 紀康、花屋 賢悟、庄司 満、須貝 威
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report

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Published: 2011-08-05   Modified: 2019-07-29  

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