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Development of chiral organocatalyst utilizing "distal group participation"

Research Project

Project/Area Number 15K05495
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

KUDO Kazuaki  東京大学, 生産技術研究所, 教授 (80251669)

Research Collaborator AKAGAWA Kengo  
SATOU Junichi  
HIGUCHI Junichi  
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2016: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2015: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Keywords有機分子触媒 / 不斉触媒 / ペプチド / ヒスチジン / プロリン / 加水分解 / ライブラリスクリーニング / Baylis-Hillman反応 / 触媒 / 協同効果 / ライブラリ / 多点活性化
Outline of Final Research Achievements

Before starting this project, we had found that a certain peptide behaves as a catalyst for a specific addition reaction with high activity and high enantioselectivity. We had uncovered that such a catalytic performance of peptide came from cooperative action of proline and histidine in the peptide chain. We tentatively named this phenomenon as "distal group participation".
This time we tried to clarify how general this "distal group participation" concept is. We tried several reactions with several peptides, and found that this concept could also be applicable toward hydrolysis reaction. In addition, we could find completely new peptide catalyst having proline and histidine. These findings show that there remains further extendability with the "distal group participation".

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (24 results)

All 2018 2017 2016 2015 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results,  Acknowledgement Compliant: 6 results) Presentation (11 results) (of which Int'l Joint Research: 2 results,  Invited: 1 results) Book (1 results) Remarks (2 results)

  • [Journal Article] Biomimetic iterative method for polyketide synthesis2017

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

      Chemical Communications

      Volume: 53 Issue: 62 Pages: 8645-8648

    • DOI

      10.1039/c7cc04033d

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of Selective Peptide Catalysts with Secondary Structural Frameworks2017

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

      Accounts of Chemical Research

      Volume: 50 Issue: 10 Pages: 2429-2439

    • DOI

      10.1021/acs.accounts.7b00211

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Helical-Peptide-Catalyzed Enantioselective Michael Addition Reaction and Their Mechanistic Insights2016

    • Author(s)
      Atsushi Ueda, Tomohiro Umeno, Mitsunobu Doi, Kengo Akagawa, Kazuaki Kudo, Masakazu Tanaka
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 81 Issue: 15 Pages: 6343-6356

    • DOI

      10.1021/acs.joc.6b00982

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Library Screening in Aqueous Media To Develop a Highly Active Peptide Catalyst for Enantioselective Michael Addition of a Malonate2016

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

      European Journal of Organic Chemistry

      Volume: - Issue: 26 Pages: 4460-4464

    • DOI

      10.1002/ejoc.201600828

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Exploration of Structural Frameworks for Reactive and Enantioselective Peptide Catalysts by Library Screenings2016

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

      The Journal of Organic Chemistry

      Volume: 81 Issue: 19 Pages: 9396-9401

    • DOI

      10.1021/acs.joc.6b01591

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Determination of the Absolute Configuration of Side Chains of Basic Amino Acid Residues Using the Water-Soluble Porphyrin-Based Exciton Chirality Method2016

    • Author(s)
      S. Hattori, K. Akagawa, K. Kudo, *K. Ishii
    • Journal Title

      J. Phys. Chem. B

      Volume: 120 Issue: 39 Pages: 10280-10287

    • DOI

      10.1021/acs.jpcb.6b07925

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Solvolysis of Formylphenyl Esters by a Bifunctional Peptide Catalyst2016

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

      Chemistry Letters

      Volume: 45 Issue: 3 Pages: 300-302

    • DOI

      10.1246/cl.151154

    • NAID

      130005132168

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Asymmetric Epoxidation of Enones by Peptide-Based Catalyst: A Strategy Inverting Juliá–Colonna Stereoselectivity2016

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

      Synlett

      Volume: 27 Issue: 08 Pages: 1217-1222

    • DOI

      10.1055/s-0035-1560597

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Kinetic Resolution of a Planar-Chiral [2.2]Paracyclophane Derivative by Helical-Peptide-Catalyzed Michael Addition of Nitromethane2015

    • Author(s)
      K. Akagawa, N. Nishi, I. Yoshikawa, K. Kudo
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2015 Issue: 23 Pages: 5055-5059

    • DOI

      10.1002/ejoc.201500594

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Peptide-Catalyzed Desymmetrization of an Achiral Ferrocenyl Compound To Induce Planar Chirality2015

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

      Eur. J. Org. Chem.

      Volume: 2015 Issue: 18 Pages: 3894-3898

    • DOI

      10.1002/ejoc.201500428

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 固相担持ペプチド触媒を用いた面不斉[n]パラシクロファンの速度論的光学分割2018

    • Author(s)
      樋口淳一,赤川賢吾,工藤一秋
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Development of Tandem Enantioselective Intramolecular Rauhut Currier Reaction and Aldol Condensation Promoted by Peptide Catalyst2018

    • Author(s)
      Y.Tian,Z.Du,K.Akagawa,K.Kudo
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 生合成機構を模倣したポリケチドの固相合成法の開発2018

    • Author(s)
      竹内優太,赤川賢吾,工藤一秋
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Development of Peptide Catalysts for Activating Substrates via Michael-Type Addition2016

    • Author(s)
      杜肇南, 赤川賢吾, 工藤一秋
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 大規模ライブラリを用いた骨格探索とファインチューニングによるペプチド触媒の開発2016

    • Author(s)
      佐藤潤一, 赤川賢吾, 工藤一秋
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] ライブラリ法による新規ペプチド触媒の探索2016

    • Author(s)
      工藤一秋
    • Organizer
      第65回高分子討論会
    • Place of Presentation
      神奈川大学
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] Development of selective peptide catalysts having secondary structures2015

    • Author(s)
      K. Kudo, K. Akagawa
    • Organizer
      International Chemical Congress of Pacific Basin Societies 2015
    • Place of Presentation
      Honolulu(USA)
    • Year and Date
      2015-12-17
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Screening of peptide libraries for discovering efficient aminocatalysts2015

    • Author(s)
      K. Akagawa, J. Satou, K. Kudo
    • Organizer
      International Chemical Congress of Pacific Basin Societies 2015
    • Place of Presentation
      Honolulu(USA)
    • Year and Date
      2015-12-16
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 大規模ライブラリスクリーニングによる新規ペプチド触媒の開発2015

    • Author(s)
      佐藤潤一, 赤川賢吾, 工藤一秋
    • Organizer
      第5回CSJ化学フェスタ
    • Place of Presentation
      船堀タワーホール(東京都)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [Presentation] Asymmetric Intramolecular Morita-Baylis-Hillman Reaction Promoted by Peptide Catalysts with Multiple Functional Groups2015

    • Author(s)
      杜肇南, 赤川賢吾, 工藤一秋
    • Organizer
      第5回CSJ化学フェスタ
    • Place of Presentation
      船堀タワーホール(東京都)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [Presentation] 第一級アミン型ペプチド不斉触媒の開発2015

    • Author(s)
      工藤一秋
    • Organizer
      第64回高分子討論会
    • Place of Presentation
      東北大学(仙台)
    • Year and Date
      2015-09-15
    • Related Report
      2015 Research-status Report
  • [Book] 有機化学2015

    • Author(s)
      工藤一秋,渡辺正
    • Total Pages
      204
    • Publisher
      化学同人
    • Related Report
      2015 Research-status Report
  • [Remarks] 発表論文

    • URL

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

    • Related Report
      2017 Annual Research Report 2015 Research-status Report
  • [Remarks] 総説・解説

    • URL

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

    • Related Report
      2017 Annual Research Report

URL: 

Published: 2015-04-16   Modified: 2019-03-29  

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