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Enzymatic oxidation and reduction using risk-free and naturally existing oxidizing or reducing agents and carbon dioxide

Research Project

Project/Area Number 25410189
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Green/Environmental chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

Matsuda Tomoko  東京工業大学, 生命理工学研究科, 准教授 (10319494)

Co-Investigator(Kenkyū-buntansha) YAMANAKA Rio  姫路獨協大学, 薬学部, 講師 (40454764)
Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥130,000 (Direct Cost: ¥100,000、Indirect Cost: ¥30,000)
Fiscal Year 2014: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Fiscal Year 2013: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsグリーンケミストリー / 酵素 / 酸素 / 二酸化炭素
Outline of Final Research Achievements

The oxidation and reduction reactions with risk-free reaction conditions were developed. The overexpressed enzymes (oxidase from Fusarium and reductase from Geotrichum candidum) using E-coli were used for the reactions, resulting in the very high efficiencies. Both enzymes have very wide substrate specificities, and excellent enantioselectivities. Especially, biotransformations of the challenging substrates for asymmetric synthesis were found to be also successful. Moreover, the structure of the G. candidum reductase was investigated by modeling and X-ray crystal structure determination to examine the mechanism to succeed in the excellent enantioselectivity.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (22 results)

All 2016 2015 2014 2013 Other

All Journal Article (5 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 2 results,  Open Access: 1 results) Presentation (14 results) (of which Invited: 2 results) Book (3 results)

  • [Journal Article] Crystallization and preliminary crystallographic analysis of acetophenone reductase from Geotrichum candidum NBRC 45972015

    • Author(s)
      Y. Sugiyama, M. Senda, T. Senda, T. Matsuda
    • Journal Title

      Acta Crystallogr.

      Volume: F71 Issue: 3 Pages: 320-323

    • DOI

      10.1107/s2053230x15002265

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Selective synthesis of cinnamyl alcohol by cyanobacterial photobiocatalysts.2015

    • Author(s)
      Rio Yamanaka, Kaoru Nakamura, Masahiko Murakami, Akio Murakami
    • Journal Title

      Tetrahedron Letters,

      Volume: 56 Issue: 9 Pages: 1089-1091

    • DOI

      10.1016/j.tetlet.2015.01.092

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Structural analysis of Geotrichum candidum alcohol dehydrogenase with excellent enantioselectivity2014

    • Author(s)
      杉山陽祐,千田美紀,千田俊哉, 松田知子
    • Journal Title

      Photon Factory Activity Report

      Volume: XXX Pages: 31-31

    • Related Report
      2014 Research-status Report
    • Open Access
  • [Journal Article] 二酸化炭素を有効利用する酵素反応の制御2014

    • Author(s)
      松田知子
    • Journal Title

      化学工学

      Volume: 78 Pages: 471-472

    • Related Report
      2014 Research-status Report
  • [Journal Article] Purification and characterization of fluorinated ketone reductase from Geotrichum candidum NBRC 57672013

    • Author(s)
      C. Cao, T. Fukae, T. Yamamoto, S. Kanamaru, T. Matsuda
    • Journal Title

      Biochem. Eng. J.

      Volume: 76 Pages: 13-16

    • DOI

      10.1016/j.bej.2013.04.005

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Fusarium sp. NBRC109816由来の Baeyer-Villiger 酸化酵素 (BVMO)による酸化反応の基質特異性の検討2016

    • Author(s)
      根本 裕海、増田彩花、松田知子
    • Organizer
      日本化学会第96春季年会(2016)
    • Place of Presentation
      同志社大学 京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Geotrichum candidum NBRC 4597 由来アルデヒド脱水素酵素の 大量発現系の構築及び諸性質の検討2016

    • Author(s)
      星野友泰、山部瑛美、松田知子
    • Organizer
      日本化学会第96春季年会(2016)
    • Place of Presentation
      同志社大学 京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Engineering of Butyl Group Specific Binding Pocket of Geotrichum candidum Acetophenone Reductase : Enantioselective Reduction of Challenging Bulky-bulky Ketones2016

    • Author(s)
      KOESOEMA, Afifa Ayu; SUGIYAMA, Yosuke; MATSUDA, Tomoko; SCHRITT, Dimitri; YAMASHITA, Kazuo; STANDLEY, Daron M.; SENDA, Miki; SENDA, Toshiya
    • Organizer
      日本化学会第96春季年会(2016)
    • Place of Presentation
      同志社大学 京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 超臨界および液体CO2を利用する酵素反応による有用物質の合成2016

    • Author(s)
      松田知子
    • Organizer
      静岡大学グローバル・サステイナブル・テクノロジー(GST)研究会
    • Place of Presentation
      東京工業大学大岡山キャンパス
    • Year and Date
      2016-03-18
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Structural Analysis and Site Directed Mutagenesis of Acetophenone Reductase (APRD) from Geotrichum candidum NBRC 45972015

    • Author(s)
      SUGIYAMA, Yosuke; KOESOEMA, Afifa Ayu; HOSHINO, Tomoyasu; MATSUDA, Tomoko; SCHRITT, Dimitri; YAMASHITA, Kazuo; STANDLEY, Daron M; SENDA, Miki; SENDA, Toshiya
    • Organizer
      日本化学会第95春季年会(2015)
    • Place of Presentation
      日本大学理工学部 船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Enhance lipase-catalyzed transesterification using liquid carbon dioxide - a green and practical approach2015

    • Author(s)
      HOANG, Nam Hai; MATSUDA, Tomoko
    • Organizer
      日本化学会第95春季年会(2015)
    • Place of Presentation
      日本大学理工学部 船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Liquid Carbon Dioxide as an Effective Solvent for immobilized Candida antartica Lipase B Catalyzed Transesterification2014

    • Author(s)
      Nam-Hai Hoang, Tomoko Matsuda
    • Organizer
      Active Enzyme Molecule 2014
    • Place of Presentation
      Toyama International Conference Center
    • Year and Date
      2014-12-17 – 2014-12-19
    • Related Report
      2014 Research-status Report
  • [Presentation] Fusarium sp.NBRC109816 による環状ケトンの Baeyer-Villiger 酸化反応の開発2014

    • Author(s)
      ムハマド・マウラナ・イフサン、蛭川絢南、河口のぞみ、増田彩花、福井秀介、 田邉知史、松田知子、北山隆
    • Organizer
      日本農芸化学会関東支部 2014 年度支部大会
    • Place of Presentation
      埼玉大学
    • Year and Date
      2014-10-18
    • Related Report
      2014 Research-status Report
  • [Presentation] 二酸化炭素が有効利用できる酵素を触媒とする有機合成法の開発2014

    • Author(s)
      松田 知子
    • Organizer
      GIC平成26年度総会および特別講演会(第37回研修セミナー)
    • Place of Presentation
      産業技術総合研究所 東北センター
    • Year and Date
      2014-04-23
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Geotrichum candidum 由来のアセトフェノン還元酵素の基質特異性の検討

    • Author(s)
      横山 絵里
    • Organizer
      生体触媒化学シンポジウム
    • Place of Presentation
      岡山理科大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Geotrichum candidum 由来のアセトフェノン還元酵素の変異体を用いる反応機構の解明

    • Author(s)
      杉山 陽祐
    • Organizer
      生体触媒化学シンポジウム
    • Place of Presentation
      岡山理科大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Fusariumu sp. による新規Baeyer-Villiger酸化反応の開発

    • Author(s)
      蛭川 絢南
    • Organizer
      生体触媒化学シンポジウム
    • Place of Presentation
      岡山理科大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Geotrichum candidum NBRC 4597由来アセトフェノン還元酵素の構造および機能解析

    • Author(s)
      杉山 陽祐
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] <i>Fusariumu</i> spによる新規新規Baeyer-Villiger酸化反応の開発

    • Author(s)
      増田 彩花
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Book] Chapter 3. Biocatalysis in organic solvents, supercritical fluids and ionic liquids, In Organic synthesis using bioctalysis, Eds. A. Goswami, J. D. Stewart2015

    • Author(s)
      C. Cao, T. Matsuda
    • Total Pages
      440
    • Publisher
      Elsevier
    • Related Report
      2015 Annual Research Report
  • [Book] (In Stereoselective synthesis of drugs and natural products)Biocatalytic asymmetric reduction of C=O and activated C=C bonds in stereoselective synthesis2013

    • Author(s)
      T. Matsuda, R. Yamanaka, K. Nakamura
    • Total Pages
      1852
    • Publisher
      Wiley
    • Related Report
      2013 Research-status Report
  • [Book] (触媒の設計・反応制御 事例集)第2章 第7節 超臨界流体の触媒反応場としての応用2013

    • Author(s)
      松田 知子
    • Total Pages
      827
    • Publisher
      (株)技術情報協会
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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