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Fine chemical production by complementary use of microbial catalysts and organic synthesis

Research Project

Project/Area Number 20580114
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, 薬学部, 教授 (60171120)

Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2010: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2009: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2008: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords有機化学 / バイオリアクター / 酵素 / 応用微生物 / リパーゼ / 鏡像選択性 / 加水分解 / 遠隔不斉認識 / 微生物還元 / 位置選択的加水分解
Research Abstract

On the screening of biocatalysts for the key steps in the total synthetic schemes, molecular design of substrates for enzyme-catalyzed reactions was thoroughly elaborated. Practical synthetic schemes themselves approaching key intermediates were also studied. As the results, three major methods for preparation were achieved : 1) the exploration of hydrolyzing enzymes which regioselectively treat the hydroxy and acyloxy groups in glycal derivatives ; 2) development of new functions of an epoxide hydrolase through the substrate specificity study ; 3) synthesis of the unique fluorine-containing aromatic substances which probe the recognition of remote chirality in the catalytic site of lipases. Based on them, novel and expeditious synthetic routes for sialidase inhibitors and a chiral analyzing agent for trace amount of biomolecules were established.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (22 results)

All 2010 2009 2008

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (8 results) Book (3 results)

  • [Journal Article] New chemo-enzymatic route toward N-acetylneuraminic acid derivatives with alkyl groups at C-7 hydroxyl group2010

    • Author(s)
      J.Calveras, Y.Nagai, I.Sultana, Y.Ueda, T.Higashi, M.Shoji, T.Sugai
    • Journal Title

      Tetrahedron 66

      Pages: 4284-4291

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] The scope and limitation on the regio- and enantioselective hydrolysis of aliphatic epoxides by Bacillus subtilis epoxide hydrolase, and exploration towards chirally differentiated tris(hydroxymethyl)methanol2010

    • Author(s)
      K.Shimizu, M.Sakamoto, M.Hamada, T.Higashi, T.Sugai, M.Shoji
    • Journal Title

      Tetrahedron : Asymmetry 21

      Pages: 2043-2049

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chemo-enzymatic Synthesis of Both Enantiomers of 2-tert-Butyl-2-methyl-1,3-benzodioxole-4-car boxylic (TBMB) Acid2010

    • Author(s)
      T.Higashi, C.Abe, K.Ninomiya, T.Machida, N.Chishima, S.Taketomi, M.Furuta, Y.Komaki, Y.Senba, T.,Tokuda M.Shoji, T.Sugai
    • Journal Title

      Adv.Synth.Catal. 352

      Pages: 2549-2558

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Elaboration on the access to (S)-4-(4-methylbenzyl)oxy-3-hydroxybutanenitrile, a key intermediate for statins, by combining the kinetic resolution of racemate and the recycle of undesired enantiomer2010

    • Author(s)
      M.Sakamoto, M.Hamada, T.Higashi, M.Shoji, T.Sugai
    • Journal Title

      J.Mol.Catal.B : Enz.

      Volume: 64 Pages: 96-100

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The scope and limitation on the regio- and enantioselective hydrolysis of aliphatic epoxides by Bacillus subtilis epoxide hydrolase, and exploration towards chirally differentiated tris(hydroxymethyl)methanol2010

    • Author(s)
      K.Shimizu, M.Sakamoto, M.Hamada, T.Higashi, T.Sugai, M.Shoji
    • Journal Title

      Tetrahedron : Asymmetry

      Volume: 21 Pages: 2043-2049

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemo-enzymatic Synthesis of Both Enantiomers of 2-tert-Butyl-2-methyl-1,3-benzodioxole-4-carboxylic (TBMB) Acid2010

    • Author(s)
      T.Higashi, C.Abe, K.Ninomiya, T.Machida, N.Chishima, S.Taketomi, M.Furuta, Y.Komaki, Y.Senba, T.Tokuda, M.Shoji, T.Sugai
    • Journal Title

      Adv.Synth.Catal

      Volume: 352 Pages: 2549-2558

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Short-step Chemo-enzymatic Synthesis of a Precursor for L-Nucleosides from D-Lyxose2009

    • Author(s)
      K.Kitsuda, J.Calveras, Y.Nagai, T.Higashi, T.Sugai
    • Journal Title

      J.Mol.Catal.B : Enz. 59

      Pages: 197-200

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] A Short-step Chemo-enzymatic Synthesis of a Precursor for L-Nucleo sides from D-Lyxose2009

    • Author(s)
      K.Kitsuda, J.Calveras, Y.Nagai, T.Higashi, T.Sugai
    • Journal Title

      Journal of Molecular Catalysis, B : Enzymatic 59

      Pages: 197-200

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enzyme-catalyzed enantiomeric resolution of 3,8-dioxatricyclo[3.2.1.02,4]octane-6-carboxylic esters and the application to the synthesis of 3-epishikimic acid2009

    • Author(s)
      M.Hamada, Y.Inami, Y.Nagai, T.Higashi, M.Shoji, S.Ogawa, K.Umezawa, T.Sugai
    • Journal Title

      Tetrahedron : Asymmetry 20

      Pages: 2105-2111

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemoenzymatic Approach to Enantiomerically Pure (R)-3-Hydroxy-3-methyl-4-pentenoic Acid Ester and Its Application to Formal Total Synthesis of Taurospongin A2008

    • Author(s)
      A. Fujino, T. Sugai
    • Journal Title

      Advanced Synthesis and Catalysis 350

      Pages: 1712-1716

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Regio- and chemoselective manipulation under mild conditions on glucosamine derivatives for oligosaccharide synthesis and its application to wards N-acetyl-D-lactosamine and Lewis X trisaccharide2008

    • Author(s)
      Y. Nagai, N. Ito, I. Sultana, T. Sugai
    • Journal Title

      Tetrahedron 64

      Pages: 9599-9606

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] Regio- and stereoselective lipase-catalyzed reactions on sugars and carbasugars (Invited Lecture)2010

    • Author(s)
      M.Hamada, Y.Ueda, N.Chishima, J.Calveras, T.Higashi, M.Shoji, T.Sugai
    • Organizer
      The International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2010-12-19
    • Related Report
      2010 Final Research Report
  • [Presentation] Regio- and Stereoselective Lipase-catalyzed Reactions on Sugars and Carbasugars2010

    • Author(s)
      M.Hamada, Y.Ueda, N.Chishima, J.Calveras, T.Higashi, M.Shoji, T.Sugai
    • Organizer
      The International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2010-12-19
    • Related Report
      2010 Annual Research Report
  • [Presentation] Recognition of Remote Chiral Centers in the Course of Lipase-Catalyzed Resolution and Its Application to Both Enantiomers of TBMB Acid (Invited Lecture)2010

    • Author(s)
      T.Sugai
    • Organizer
      BIT's Inaugural Symposium on Enzymes & Biocatalysis
    • Place of Presentation
      Shanghai
    • Year and Date
      2010-04-24
    • Related Report
      2010 Final Research Report
  • [Presentation] 微生物酵素を用いた不斉中心導入に基づくスタチン類の合成研究2009

    • Author(s)
      坂本真希, 濱田学, 東利則, 庄司満, 須貝威
    • Organizer
      第13回生体触媒化学シンポジウム
    • Place of Presentation
      香川県(香川大学)
    • Year and Date
      2009-12-03
    • Related Report
      2009 Annual Research Report
  • [Presentation] 枯草菌エポキシヒドロラーゼの基質特異性解明について2009

    • Author(s)
      清水賢一, 坂本真希, 濱田学, 東利則, 庄司満, 須貝威
    • Organizer
      第13回生体触媒化学シンポジウム
    • Place of Presentation
      香川県(香川大学)
    • Year and Date
      2009-12-03
    • Related Report
      2009 Annual Research Report
  • [Presentation] 含フッ東芳香族化合物の不斉還元・速度論的光学分割に関する検討2008

    • Author(s)
      阿部智香, 岩永裕作, 東利則, 中村薫, 須貝威
    • Organizer
      第12回生体触媒化学シンポジウム
    • Place of Presentation
      船橋市(東邦大学)
    • Year and Date
      2008-12-04
    • Related Report
      2008 Annual Research Report
  • [Presentation] 加水分解酵東を用いた2, 2-ジ置換シアノ酢酸エステル類の速度論的光学分割2008

    • Author(s)
      辰巳裕紀, 濱田学, 東利則, 須貝威
    • Organizer
      第12回生体触媒化学シンポジウム
    • Place of Presentation
      船橋市(東邦大学)
    • Year and Date
      2008-12-04
    • Related Report
      2008 Annual Research Report
  • [Presentation] 多様な微生物起源に由来するエポキシドヒドロラーゼの基質特異性の比較2008

    • Author(s)
      坂本真希, 濱田学, 藤野彩, 東利則, 須貝威
    • Organizer
      第12回生体触媒化学シンポジウム
    • Place of Presentation
      船橋市(東邦大学)
    • Year and Date
      2008-12-04
    • Related Report
      2008 Annual Research Report
  • [Book] 複合糖質の化学と最新応用技術(正田晋一郎、稲津敏行編)(位置・立体選択的反応を鍵段階とする酵素-化学複合合成法の開発)2009

    • Author(s)
      橘田和憲、濱田学、梅澤一夫、東利則、須貝威
    • Publisher
      シーエムシー
    • Related Report
      2010 Final Research Report
  • [Book] Practical Methods for Biocatalysis and Biotransformations (J.Whittal, P.W.Sutton,eds.) (Epoxide Hydrolase Catalyzed Synthesis of (R)-3-benzyloxy-2-methylpropane-1,2-diol)2009

    • Author(s)
      T.Sugai, A.Fujino, H.Yamaguchi, M.Ikunaka
    • Related Report
      2010 Final Research Report
  • [Book] 酵素反応のスケールアップ-トラブル解決へのヒント-2008

    • Author(s)
      須貝威, 濱田学
    • Total Pages
      12
    • Publisher
      シーエムシー
    • Related Report
      2008 Annual Research Report

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Published: 2008-04-01   Modified: 2016-04-21  

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