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Regioselective Cleavage of Peptides by Organocatalysis

Research Project

Project/Area Number 25670004
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionKyoto University

Principal Investigator

KAWABATA Takeo  京都大学, 化学研究所, 教授 (50214680)

Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords有機触媒 / ペプチド / 位置選択的切断 / アミド結合 / 短縮反応
Outline of Final Research Achievements

Non-enzymatic peptide cleavage under mild conditions has been a long-standing challenge in organic synthesis. A further challenge is how to achieve site-selectivity in the peptide cleavage. We report here organocatalytic site-selective cleavage of serine-containing peptides at ambient temperature. The salient feature of this reaction is that the peptide cleavage takes place at the both N-, and C-termini of the serine residue, and the remaining peptides at the both side of the serine residue recombine keeping their original sequences. The serine residue is excluded and recovered as an oxazolidone derivative. This splicing-type reaction was observed with high generality and high functional group tolerance.

Report

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

    (7 results)

All 2015 2014 2013

All Journal Article (4 results) (of which Peer Reviewed: 4 results,  Acknowledgement Compliant: 2 results) Presentation (3 results)

  • [Journal Article] Origin of High E-Selectivity in 4-Pyrrolidinopyridine-Catalyzed Tetrasubstituted α,α’-Alkenediol: A Computational and Experimental Study2015

    • Author(s)
      Yamanaka, M.; Yoshida, U.; Sato, M.; Shigeta, T.; Yoshida, K.; Furuta, T.; Kawabata, T.
    • Journal Title

      J. Org. Chem.

      Volume: 80 Issue: 6 Pages: 3075-3082

    • DOI

      10.1021/jo5029453

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Total synthesis of ellagitannins through regioselective sequential functionalization of unprotected glucose2015

    • Author(s)
      H. Takeuchi, K. Mishiro, Y. Ueda, Y. Fujimori, T. Furuta, T. Kawabata
    • Journal Title

      Angewandte Chemie International Edition

      Volume: in press Issue: 21 Pages: 6177-6180

    • DOI

      10.1002/anie.201500700

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Oxidative kinetic resolution of racemic alkyl aryl carbinols by an electronically tuned chiral nitroxyl radical2014

    • Author(s)
      Hamada, S.; Wada, Y.; Sasamori, T.; Tokitoh, N.; Furuta, T.; Kawabata, T.
    • Journal Title

      Tetrahedron Lett

      Volume: 55 Issue: 11 Pages: 1943-1945

    • DOI

      10.1016/j.tetlet.2014.02.005

    • NAID

      120005439590

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] アシル化触媒2014

    • Author(s)
      川端猛夫
    • Journal Title

      月刊ファインケミカル

      Volume: 63 Pages: 14-23

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Presentation] 有機触媒を用いる常温・中性条件下でのペプチドの位置選択的解裂2014

    • Author(s)
      早坂 茉奈美、木下 智彦、三代 憲司、川端 猛夫
    • Organizer
      有機分子触媒による未来型分子変換 第4回公開シンポジウム
    • Place of Presentation
      北海道大学学術交流会館(北海道札幌市)
    • Year and Date
      2014-06-20 – 2014-06-21
    • Related Report
      2014 Annual Research Report
  • [Presentation] 精密分子認識に基づくSer含有ペプチドの位置選択的切断2014

    • Author(s)
      早阪 茉奈美,木下 智彦,三代 憲司,川端 猛夫
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本大学・熊本
    • Related Report
      2013 Research-status Report
  • [Presentation] 有機触媒によるペプチドの位置選択的解裂-脱セリン化反応2013

    • Author(s)
      早阪 茉奈美,木下 智彦,三代 憲司,川端 猛夫
    • Organizer
      第63回日本薬学会近畿支部総会・大会
    • Place of Presentation
      同志社女子大学 京田辺キャンパス・京都
    • Related Report
      2013 Research-status Report

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

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