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Efficient organic synthesis utilizing microbial enzyme catalysts

Research Project

Project/Area Number 26450143
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

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

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2015: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords立体選択的反応 / 位置選択的反応 / リパーゼ触媒 / ポリフェノール / 複素環化合物 / リパーゼ / 含窒素複素環 / 速度論的分割 / 脱アセチル化 / エステル交換 / 遠隔位不斉中心
Outline of Final Research Achievements

Complementary and synergistic utilization of enzyme-catalyzed reactions and chemical transformation was studied, toward the efficient synthesis of complex target molecules involving valuable natural and unnatural products. The achievements are shown below. Lipase-catalyzed transesterification proceeded with specific site-selectivity contrasting to chemical transformations, and the syntheses of selinone and astringin, artepillin C became successful. It was revealed that the transesterification under non-aqueous conditions was advantageous for the substrates which are labile to water and/or prone to protonation under aqueous conditions. The preparation of highly enantiomerically pure (R)-3-hydroxy-N-methylpiperidine by the lipase-catalyzed kinetic resolution of corresponding racemate was established. The synthesis of enantiomers of NMB carboxylic acid was also successful, by discriminating he stereochemistry of remote chiral center in a primary acetate, as the key step.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (13 results)

All 2017 2016 2015 2014 Other

All Int'l Joint Research (1 results) Journal Article (5 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 5 results,  Acknowledgement Compliant: 5 results,  Open Access: 1 results) Presentation (5 results) (of which Int'l Joint Research: 2 results) Book (2 results)

  • [Int'l Joint Research] Department of Chemistry,/Graduate School of SIGMA Clermont(France)

    • Related Report
      2016 Annual Research Report
  • [Journal Article] Preparation of (R)-3-hydroxy-N-methylpiperidine, a synthetic key intermediate of (R)-mepenzolate, based on the lipase-catalyzed resolution of the racemic form.2017

    • Author(s)
      Yamashita, Y., Hanaya, K., Shoji, M., and Sugai, T.
    • Journal Title

      Heterocycles

      Volume: 95 Issue: 1 Pages: 370-379

    • DOI

      10.3987/com-16-s(s)28

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation2017

    • Author(s)
      Y. Yamashita, A. Biard, K. Hanaya, M. Shoji, T. Sugai
    • Journal Title

      Bioscience, Biotechnology and Biochemistry

      Volume: - Issue: 7 Pages: 1279-1284

    • DOI

      10.1080/09168451.2017.1303362

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Simple Synthesis of Sakuranetin and Selinone <i>via</i> a Common Intermediate, Utilizing Complementary Regioselectivity in the Deacetylation of Naringenin Triacetate2016

    • Author(s)
      Y. Yamashita, K. Hanaya, M. Shoji, T. Sugai
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 64 Issue: 7 Pages: 961-965

    • DOI

      10.1248/cpb.c16-00190

    • NAID

      130005160036

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] New Synthesis of Artepillin C, a Prenylated Phenol, Utilizing Lipase-catalyzed Regioselective Deacetylation as the Key Step2015

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

      Bioscience, Biotechnology and Biochemistry

      Volume: 79 Issue: 12 Pages: 1926-1930

    • DOI

      10.1080/09168451.2015.1058704

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Recognition of the remote chiral center in lipase-catalyzed kinetic resolution of [2-methyl-2-(2′-naphthyl)-1,3-benzodioxol-4-yl]methyl acetate, the precursor of 2-methyl-2-(2′-naphthyl)-1,3-benzodioxole-4-carboxylic acid (MNB carboxylic acid)2014

    • Author(s)
      N. Natori, K. Nakagawara, M. Shoji, T. Sugai, K. Hanaya
    • Journal Title

      Journal of Molecular Catalysis B: Enzymatic

      Volume: 109 Pages: 130-135

    • DOI

      10.1016/j.molcatb.2014.08.010

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 酵素触媒の位置選択性を活用したポリフェノール類の合成研究2016

    • Author(s)
      坂倉彩香, 山下泰信, 恒川龍二, 野城和貴, 花村 駿, 花屋賢悟, 庄司 満, 須貝 威
    • Organizer
      生体触媒化学シンポジウム
    • Place of Presentation
      明星大学、東京都日野市
    • Year and Date
      2016-12-21
    • Related Report
      2016 Annual Research Report
  • [Presentation] Advantage of enzyme-catalyzed acetylation and deacetylation in the synthesis of useful products2016

    • Author(s)
      Yamashita Y, Hanaya K, Shoji M, Sugai T
    • Organizer
      The Fifth International Conference on Cofactors (ICC-05) and Active Enzyme Molecule 2016 (AEM 2016)
    • Place of Presentation
      Kurobe Unazuki International Hall Selene, 富山県黒部市
    • Year and Date
      2016-09-04
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 配糖体と酵素触媒を活用する、有用ポリフェノール類の合成研究2015

    • Author(s)
      須貝 威、花村駿、花屋賢悟、庄司満、木内文之
    • Organizer
      日本農芸化学会関東支部2015年度支部大会
    • Place of Presentation
      お茶の水女子大学(東京都)
    • Year and Date
      2015-09-26
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthesis of Artepillin C, Based on Lipase-Catlayzed Regioselective Deacetylation2015

    • Author(s)
      Yashiro, K.; Hanaya, K.; Shoji, M.; Sugai, T.
    • Organizer
      Biotrans 2015
    • Place of Presentation
      Wiena (Austria)
    • Year and Date
      2015-07-26
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] リパーゼによる遠隔位不斉認識を利用したMNBカルボン酸の合成2014

    • Author(s)
      名取直輝、花屋賢悟、庄司満、須貝威
    • Organizer
      有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      慶應義塾大学理工学部(横浜)
    • Year and Date
      2014-05-17
    • Related Report
      2014 Research-status Report
  • [Book] Site-selective lipase-catalyzed acylation and deacylation in the synthesis of valuable carbohydrates and flavonoids from naturally abundant starting materials2017

    • Author(s)
      R. Tsunekawa, K. Hanaya, M. Shoji, T. Sugai
    • Total Pages
      17
    • Publisher
      Elsevier B. V.
    • Related Report
      2016 Annual Research Report
  • [Book] 有機合成実験法ハンドブック第2版2015

    • Author(s)
      須貝 威、古田未有
    • Total Pages
      3
    • Publisher
      丸善
    • Related Report
      2015 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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