• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to project page

2011 Fiscal Year Final Research Report

Development of a new method for peptide ligation based on the N-S acyl shift reaction

Research Project

  • PDF
Project/Area Number 21550155
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemistry related to living body
Research InstitutionOsaka University

Principal Investigator

KAWAKAMI Toru  大阪大学, 蛋白質研究所, 准教授 (70273711)

Project Period (FY) 2009 – 2011
Keywords蛋白質 / ペプチド / 合成化学 / ライゲーション / ペプチドチオエステル
Research Abstract

The peptide thioester is used as a building block for protein synthesis. In this research, we developed new methods for the peptide thioester synthesis. Based on the structure of Cys-Pro ester(CPE), Cys-Pro-Cys sequence was found to produce a peptide thioester. It could be prepared as a recombinant protein. When N-substitute Gly residue is introduced instead of the Pro residue in the CPE structure, this CNGE peptide produces the thioester more efficiently than the CPE peptide.

  • Research Products

    (27 results)

All 2012 2011 2010 2009 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (15 results) Book (1 results) Remarks (1 results)

  • [Journal Article] N-Sアシル基転位反応を用いるペプチドチオエステル合成法の開発2012

    • Author(s)
      川上徹, 相本三郎
    • Journal Title

      有機合成化学協会誌

      Volume: 70巻 Pages: 166-176

    • Peer Reviewed
  • [Journal Article] Formation of peptide thioesters by the use of modified Cys-Pro Ester(CPE) autoactivating unit2012

    • Author(s)
      A. Kamauchi, E. Harada, S. Aimoto, T. Kawakami
    • Journal Title

      Peptide Science 2011

      Pages: 135-136

    • Peer Reviewed
  • [Journal Article] Peptide Ligation via thioester formation at the cysteine residue2011

    • Author(s)
      T. Kawakami, S. Aimoto
    • Journal Title

      Peptide Science 2010, Japanese Peptide Society

      Pages: 47

    • Peer Reviewed
  • [Journal Article] Peptide Diketopiperazine Thioester Formation at the Cys-Pro-Cys Position2010

    • Author(s)
      T. Kawakami, S. Shimizu, S. Aimoto
    • Journal Title

      Peptides 2010 : Tales of Peptides, European Peptide Society

      Pages: 52-53

    • Peer Reviewed
  • [Journal Article] Peptide Thioester Formation by an N to S Acyl Shift Reaction at the Cysteinyl Prolyl Cysteine Position2010

    • Author(s)
      T. Kawakami, S. Shimizu, S. Aimoto
    • Journal Title

      Bulletin of Chemical Society of Japan

      Volume: 83巻 Pages: 570-574

    • Peer Reviewed
  • [Journal Article] Synthesis of peptide thioesters based on an N to S acyl shift reaction2010

    • Author(s)
      T. Kawakami, S. Shimizu, S. Aimoto
    • Journal Title

      Peptide Science 2009, Japanese Peptide Society

      Pages: 79-80

    • Peer Reviewed
  • [Journal Article] Formation of peptide thioesters by an N to S acyl shift reaction at the cysteinyl prolyl cysteine position2010

    • Author(s)
      S. Shimizu, S. Aimoto, T. Kawakami
    • Journal Title

      Peptide Science 2009, Japanese Peptide Society

      Pages: 153-154

    • Peer Reviewed
  • [Journal Article] The use of a cysteinyl prolyl ester(CPE) autoactivating unit in peptide ligation reactions2009

    • Author(s)
      T. Kawakami, S. Aimoto
    • Journal Title

      Tetrahedron

      Volume: 65巻 Pages: 3871-3877

    • Peer Reviewed
  • [Journal Article] Synthesis of peptide thioesters via an N-S acyl shift reaction under mild acidic conditions on an N-4, 5-dimethoxy-2-mercaptobenzyl auxiliary group2009

    • Author(s)
      K. Nakamura, T. Kanao, T. Uesugi, T. Hara, T. Sato, T. Kawakami, S. Aimoto
    • Journal Title

      Journal of Peptide Science

      Volume: 15巻 Pages: 731-737

    • Peer Reviewed
  • [Journal Article] Peptide thioester formation and ligation using a cysteinyl prolyl ester(CPE) autoactivating unit, Peptides2009

    • Author(s)
      T. Kawakami, S. Aimoto
    • Journal Title

      American peptide Society

      Pages: 29-30

    • Peer Reviewed
  • [Presentation] 改良型CPE自発的活性化ユニットによるペプチドチオエステル形成2012

    • Author(s)
      鎌内彬貴, 川上徹, 相本三郎
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学,横浜
    • Year and Date
      2012-03-27
  • [Presentation] Synthesis of peptide thioesters by the use of an N-S acyl shift reaction for peptide ligation2011

    • Author(s)
      川上徹
    • Organizer
      第14回ペプチドフォーラム
    • Place of Presentation
      鹿児島大学,鹿児島
    • Year and Date
      2011-12-16
  • [Presentation] Formation of peptide thioesters by the use of modified Cys-Pro Ester(CPE) autoactivating unit2011

    • Author(s)
      A. Kamauchi, E. Harada, S. Aimoto, T. Kawakami
    • Organizer
      第48回ペプチド討論会
    • Place of Presentation
      札幌コンベンションセンター,札幌
    • Year and Date
      2011-09-28
  • [Presentation] チオエステルライゲーション法による蛋白質合成:システイン残基でのN-Sアシル基転位反応を経由するペプチドチオエステル形成2011

    • Author(s)
      川上徹, 清水咲子, 相本三郎
    • Organizer
      第11回日本蛋白質科学会年会
    • Place of Presentation
      ホテル阪急エキスポパーク,吹田
    • Year and Date
      2011-06-07
  • [Presentation] CPE自己活性化ユニットを用いたリポソーム内でのチオエステル形成2011

    • Author(s)
      假屋園大和, 川上徹, 相本三郎
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学,横浜
    • Year and Date
      2011-03-28
  • [Presentation] Cys-Proエステル(CPE)自己活性化ユニットの改良によるペプチドチオエステル調製法の効率化2011

    • Author(s)
      鎌内彬貴, 川上徹, 相本三郎
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学,横浜
    • Year and Date
      2011-03-28
  • [Presentation] ライゲーション法による長鎖ペプチド合成: N-Sアシル基転位反応を基盤とするペプチドチオエステル合成ブロックの合成法を中心に2011

    • Author(s)
      川上徹
    • Organizer
      第5回プロセス化学ラウンジ
    • Place of Presentation
      琵琶レイクオーツカ,大津
    • Year and Date
      2011-02-03
  • [Presentation] Peptide ligation via thioester formation at the cysteine residue2010

    • Author(s)
      T. Kawakami, S. Aimoto
    • Organizer
      5^<th> International Peptide Symposium
    • Place of Presentation
      京都国際会議場,京都
    • Year and Date
      2010-12-09
  • [Presentation] Peptide Diketopiperazine-thioester formation via an N-S acyl shift reaction at the amide bond between-Xaa-Cys-in the-Xaa-Cys-Pro-Cys-sequence2010

    • Author(s)
      T. Kawakami, S. Shimizu, S. Aimoto
    • Organizer
      The 13th Akabori Conference
    • Place of Presentation
      Leipzig
    • Year and Date
      2010-09-14
  • [Presentation] Peptide diketopiperazine thioester formation at the Cys-Pro-Cys position2010

    • Author(s)
      T. Kawakami, S. Shimizu, S. Aimoto
    • Organizer
      31st European Peptide Symposium
    • Place of Presentation
      Copenhagen
    • Year and Date
      2010-09-06
  • [Presentation] Cys-Pro-Cys部位におけるN-Sアシル基転位反応を利用したペプチドチオエステルの合成2010

    • Author(s)
      清水咲子, 相本三郎, 川上徹
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学,東大阪
    • Year and Date
      2010-03-27
  • [Presentation] Peptide ligation based on an N to S acyl shift reaction2009

    • Author(s)
      T. Kawakami, S. Aimoto
    • Organizer
      ICCEOCA-4
    • Place of Presentation
      Bangkok
    • Year and Date
      2009-12-02
  • [Presentation] Formation of peptide thioesters by an N to S acyl shift reaction at the cysteinyl prolyl cysteine position2009

    • Author(s)
      S. Shimizu, T. Kawakami, S., Aimoto
    • Organizer
      第46回ペプチド討論会
    • Place of Presentation
      北九州国際会議場,北九州
    • Year and Date
      2009-11-05
  • [Presentation] Synthesis of peptide thioester based on N to S acyl shift reaction2009

    • Author(s)
      T. Kawakami, S. Shimizu, S., Aimoto
    • Organizer
      第46回ペプチド討論会
    • Place of Presentation
      北九州国際会議場,北九州
    • Year and Date
      2009-11-05
  • [Presentation] Peptide thioester formation and ligation using a cysteinyl prolyl ester(CPE) autoactivating unit2009

    • Author(s)
      T. Kawakami, S. Aimoto
    • Organizer
      21th American Peptide Symposium
    • Place of Presentation
      Broomington
    • Year and Date
      2009-06-09
  • [Book] 最新ペプチド合成技術とその創薬研究への応用2012

    • Author(s)
      川上徹, 相本三郎
    • Total Pages
      76-82
    • Publisher
      メディカルドゥ
  • [Remarks]

    • URL

      http://www.protein.osaka-u.ac.jp/organic/index.html

URL: 

Published: 2013-07-31  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi