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Development of highly active peptide catalysts by library screening

Research Project

Project/Area Number 15K17851
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic 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) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2015: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Keywordsペプチド触媒 / ライブラリスクリーニング / コンビナトリアル化学 / 不斉マイケル付加
Outline of Final Research Achievements

A facile screening method for finding active catalysts from the peptide library constructed in a combinatorial manner has been established. With this method, novel bifunctional peptide catalysts having N-terminal proline and a histidyl residue ware developed. The screening in aqueous media afforded the prolyl peptide with a lysine residue. In the presence of these peptide catalysts, asymmetric Michael addition could be performed with high efficiency and enantioselectivity. Notably, two kinds of histidine-containing peptides showed opposite enantioselectivities, although both peptides had common N-terminal residues. By applying the screening method to the reaction that could not be performed with other catalysts, the peptide effective for that reaction was successfully identified.

Report

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

    (20 results)

All 2017 2016 2015 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results,  Acknowledgement Compliant: 6 results) Presentation (10 results) (of which Int'l Joint Research: 3 results,  Invited: 2 results) Book (1 results) Remarks (1 results)

  • [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 Annual Research 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 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [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 Annual Research Report
    • Peer Reviewed
  • [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 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solvolysis of Formylphenyl Esters by a Bifunctional Peptide Catalyst2016

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

      Chemistry Letters

      Volume: 45 Pages: 300-302

    • NAID

      130005132168

    • 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] 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
  • [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
  • [Presentation] Development of Active Peptides for Asymmetric Catalysis by Library Screening2017

    • Author(s)
      Kengo Akagawa
    • Organizer
      Protein & Peptide Conference-2017
    • Place of Presentation
      Hilton Fukuoka Sea Hawk(福岡)
    • Year and Date
      2017-03-22
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 選択的反応のためのペプチド触媒の開発2016

    • Author(s)
      赤川 賢吾
    • Organizer
      日本薬学会 第136年会
    • Place of Presentation
      パシフィコ横浜 (神奈川県・横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
    • Invited
  • [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探索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 京田辺キャンパス (京都府・京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status 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 京田辺キャンパス (京都府・京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 水系溶媒中でのライブラリスクリーニングによる新規ペプチド触媒の創製2016

    • Author(s)
      赤川 賢吾、岩﨑 由美香、工藤 一秋
    • Organizer
      「有機分子触媒」第6回公開シンポジウム
    • Place of Presentation
      大阪科学技術センター (大阪府・大阪市西区)
    • Year and Date
      2016-01-22
    • Related Report
      2015 Research-status Report
  • [Presentation] 励起子キラリティー法を用いたペプチドの円偏光二色性解析2016

    • Author(s)
      服部伸吾、赤川賢吾、工藤一秋、石井和之
    • Organizer
      光電子融合研究センター公開シンポジウム~光電子融合と先端材料~
    • Place of Presentation
      東京大学生産技術研究所(東京)
    • Related Report
      2016 Annual Research Report
  • [Presentation] Screening of peptide libraries for discovering efficient aminocatalysts2015

    • Author(s)
      Kengo Akagawa
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [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 2015
    • Place of Presentation
      タワーホール船堀 (東京都・江戸川区)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [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 2015
    • Place of Presentation
      タワーホール船堀 (東京都・江戸川区)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [Presentation] Development of efficient peptide catalysts by a facile library screening method2015

    • Author(s)
      Kengo Akagawa
    • Organizer
      The 39th Naito Conference
    • Place of Presentation
      シャトレーゼ ガトーキングダム サッポロ (北海道・札幌市)
    • Year and Date
      2015-07-06
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Book] Encyclopedia of Reagents for Organic Synthesis [Online]2016

    • Author(s)
      Kengo Akagawa
    • Total Pages
      4
    • Publisher
      John Wiley & Sons Ltd.
    • Related Report
      2016 Annual Research Report
  • [Remarks] 東京大学生産技術研究所工藤研究室ホームページ

    • URL

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

    • Related Report
      2016 Annual Research Report 2015 Research-status Report

URL: 

Published: 2015-04-16   Modified: 2018-03-22  

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