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Development of environmentally benign systems by combiniengzymaen and organocatalyst

Research Project

Project/Area Number 23750171
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Environmental chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

AKAGAWA Kengo  東京大学, 生産技術研究所, 助教 (60548733)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2012: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2011: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Keywordsペプチド触媒 / 有機触媒 / 酸化酵素 / 不斉合成 / 連続反応 / ラッカーゼ / 不斉酸化反応 / オキシアミノ化反応
Research Abstract

A novel catalytic system using a peptide catalyst and an enzyme in one-pot was developed. By combining the activation with the peptide having a terminal amino group and air oxidation with the enzyme, asymmetric alpha-oxyamination of saturated aldehydes was realized. This was extended to the sequential reaction, in which alpha,beta-unsaturated aldehydes were efficiently converted to highly functionalized products in one-pot.

Report

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

    (29 results)

All 2013 2012 2011 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results) Presentation (20 results) Remarks (1 results)

  • [Journal Article] Asymmetric induction by helical poly(amino acid) in cyanosilylation of aldehydes2012

    • Author(s)
      K. Akagawa, K. Kudo
    • Journal Title

      Tetrahedron Lett.

      Volume: 53 Issue: 45 Pages: 5981-5983

    • DOI

      10.1016/j.tetlet.2012.07.034

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric one-pot sequential Friedel-Crafts-type alkylation and α-oxyamination catalyzed by a peptide and an enzyme2012

    • Author(s)
      K. Akagawa, R. Umezawa, K. Kudo
    • Journal Title

      Beilstein J. Org. Chem.

      Volume: 8 Pages: 1333-1337

    • DOI

      10.3762/bjoc.8.152

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Construction of an All-Carbon Quaternary Stereocenter by the Peptide-Catalyzed Asymmetric Michael Addition of Nitromethane to beta-Disubstituted alpha,beta-Unsaturated Aldehydes2012

    • Author(s)
      Kengo Akagawa, Kazuaki Kudo
    • Journal Title

      Angewandte Chemie International Edition

      Volume: Vol.51 Pages: 12786-12789

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Effect of the Helical Tether of a Resin-Supported Peptide Catalyst for Friedel-Crafts-Type Alkylation in Water2012

    • Author(s)
      K. Akagawa, R. Suzuki, K. Kudo
    • Journal Title

      Adv. Synth. Catal.

      Volume: 354 Issue: 7 Pages: 1280-1286

    • DOI

      10.1002/adsc.201100950

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Michael addition of boronic acids to a gamma-hydroxy-alpha,beta- unsaturated aldehyde catalyzed by resin-supported peptide2012

    • Author(s)
      Kengo Akagawa, Masahide Sugiyama, Kazuaki Kudo
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: Vol.10 Pages: 4839-4843

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric induction by helical poly(amino acid)s in cyanosilylation of aldehydes2012

    • Author(s)
      Kengo Akagawa, Kazuaki Kudo
    • Journal Title

      Tetrahedron Letters

      Volume: Vol.53 Pages: 5981-5983

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Construction of an All-Carbon Quaternary Stereocenter by the Peptide-Catalyzed Asymmetric Michael Addition of Nitromethane to β-Disubstituted α,β-Unsaturated Aldehydes2012

    • Author(s)
      K. Akagawa, K. Kudo
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 51 Issue: 51 Pages: 12786-12789

    • DOI

      10.1002/anie.201206916

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Peptide/Laccase Cocatalyzed Asymmetric alpha-Oxyamination of Aldehyde2011

    • Author(s)
      Kengo Akagawa, Kazuaki Kudo
    • Journal Title

      Organic Letters

      Volume: Vol.13 Pages: 3498-3501

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Presentation] "Peptide-catalyzed regio- and enantioselectivereduction"有機分子触媒による未来型分子変換2013

    • Author(s)
      赤川賢吾,洗洵,工藤一秋
    • Organizer
      第1回国際会議
    • Place of Presentation
      大津プリンスホテル(滋賀県)
    • Year and Date
      2013-05-27
    • Related Report
      2012 Final Research Report
  • [Presentation] ペプチド触媒を用いた面不斉フェロセンの速度論的光学分割2013

    • Author(s)
      秋山みどり,赤川賢吾,工藤一秋
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス(滋賀県)
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] 第一級アミノ基を活性部位とするペプチ2013

    • Author(s)
      鈴木理恵子,赤川賢吾,工藤一秋
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス(滋賀県)
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] 第一級アミノ基を活性部位とするペプチド触媒を用いた不斉Michael付加反応2013

    • Author(s)
      鈴木理恵子
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス (滋賀県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] ペプチド触媒を用いた面不斉フェロセンの速度論的光学分割2013

    • Author(s)
      秋山みどり
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス (滋賀県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Construction of All-Carbon Quaternary Stereocenter by Asymmetric Michael Addition of Nitromethane to beta,beta-Disubstituted Aldehydes with Peptide Catalyst2012

    • Author(s)
      赤川賢吾,工藤一秋
    • Organizer
      IKCOC-12
    • Place of Presentation
      京都リーガロイヤルホテル(京都府)
    • Year and Date
      2012-11-15
    • Related Report
      2012 Final Research Report
  • [Presentation] ペプチド触媒を用いたss,ss-二置換α,β-不飽和アルデヒドへのニトロメタンのMichael付加による不斉四級炭素中心の構築2012

    • Author(s)
      赤川賢吾,工藤一秋
    • Organizer
      第5回有機触媒シンポジウム
    • Place of Presentation
      学習院大学(東京都)
    • Year and Date
      2012-10-27
    • Related Report
      2012 Final Research Report
  • [Presentation] 第一級アミノ基を活性部位とするペプチドを用いた不斉触媒反応2012

    • Author(s)
      鈴木理恵子,赤川賢吾,工藤一秋
    • 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
    • Year and Date
      2012-10-16
    • Related Report
      2012 Final Research Report
  • [Presentation] 新規スクリーニング法による高効率ペプチド有機触媒の探索(2)2012

    • Author(s)
      長嶺イマン翔,酒井信孝,赤川賢吾,工藤一秋
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス・矢上キャンパス(神奈川県)
    • Year and Date
      2012-03-26
    • Related Report
      2012 Final Research Report
  • [Presentation] 新規スクリーニング法による高効率ペプチド有機触媒の探索(1)2012

    • Author(s)
      酒井信孝,長嶺イマン翔,赤川賢吾工藤一秋
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス・矢上キャンパス(神奈川県)
    • Year and Date
      2012-03-26
    • Related Report
      2012 Final Research Report
  • [Presentation] ポリアミノ酸を第一級アミン触媒として用いる不斉分子変換2012

    • Author(s)
      鈴木理恵子,赤川賢吾,工藤一秋
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス・矢上キャンパス(神奈川県)
    • Year and Date
      2012-03-26
    • Related Report
      2012 Final Research Report
  • [Presentation] ペプチド触媒を用いたアルデヒドの不斉α-アミノ化2012

    • Author(s)
      田中辰佳,赤川賢吾,満田勝,工藤一秋
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス・矢上キャンパス(神奈川県)
    • Year and Date
      2012-03-26
    • Related Report
      2012 Final Research Report
  • [Presentation] 樹脂固定化ペプチド触媒を用いたα,ss,γ,δ-不飽和アルデヒドへの位置選択的1,6-付加反応2012

    • Author(s)
      洗洵,赤川賢吾,工藤一秋
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス・矢上キャンパス(神奈川県)
    • Year and Date
      2012-03-26
    • Related Report
      2012 Final Research Report
  • [Presentation] 固相担持ペプチド触媒を用いたアルケニルボロン酸のα,β-不飽和アルデヒドへの不斉マイケル付加反応2012

    • Author(s)
      杉山尚秀,赤川賢吾,工藤一秋
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス・矢上キャンパス(神奈川県)
    • Year and Date
      2012-03-25
    • Related Report
      2012 Final Research Report
  • [Presentation] ペプチド触媒と酵素を用いたFriedel-Crafts型アルキル化/オキシアミノ化one-pot連続不斉反応2012

    • Author(s)
      梅澤遼太,赤川賢吾,工藤一秋
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス・矢上キャンパス(神奈川県)
    • Year and Date
      2012-03-25
    • Related Report
      2012 Final Research Report
  • [Presentation] ペプチド触媒を用いたβ,β-二置換α,β-不飽和アルデヒドへのニトロメタンのMichael 付加による不斉四級炭素中心の構築2012

    • Author(s)
      赤川賢吾
    • Organizer
      第5回 有機触媒シンポジウム
    • Place of Presentation
      学習院大学 (東京都)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 第一級アミノ基を活性部位とするペプチドを用いた不斉触媒反応2012

    • Author(s)
      鈴木理恵子
    • 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 (東京都)
    • Related Report
      2012 Annual Research Report
  • [Presentation] ペプチド触媒と酵素を用いたFriedel-Crafts型アルキル化/オキシアミノ化one-pot連続不斉反応2012

    • Author(s)
      梅澤 遼太、赤川 賢吾、工藤 一秋
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      神奈川
    • Related Report
      2011 Research-status Report
  • [Presentation] ペプチド触媒と酵素を用いたアルデヒドの不斉α-オキシアミノ化反応2011

    • Author(s)
      赤川賢吾,工藤一秋
    • Organizer
      第4回有機触媒シンポジウム
    • Place of Presentation
      東京理科大学神楽坂キャンパス(東京都)
    • Year and Date
      2011-09-17
    • Related Report
      2012 Final Research Report
  • [Presentation] ペプチド触媒と酵素を用いたアルデヒドの不斉α-オキシアミノ化反応2011

    • Author(s)
      赤川 賢吾、工藤 一秋
    • Organizer
      第4回有機触媒シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2011 Research-status Report
  • [Remarks]

    • URL

      http://www.iis.u-tokyo.ac.jp/~kkudo/index.html

    • Related Report
      2012 Final Research Report

URL: 

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

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