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Development of a new convergent one-pot peptide ligation for the facile synthesis of glycoproteins and its crystallography

Research Project

Project/Area Number 16K05844
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Bio-related chemistry
Research InstitutionOsaka University

Principal Investigator

Okamoto Ryo  大阪大学, 理学研究科, 講師 (30596870)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2018: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsタンパク質化学合成 / ペプチドライゲーション / ペプチド-グアニジド / エリスロポエチン / ワンポット / ペプチドーピバロイルグアニジン / ネイティブケミカルライゲーション / タンパク質 / ペプチド / 糖タンパク質 / ピバロイルグアニジン / ピバロイルグアニジド / N-ピバロイルグアニジン / ペプチドグアニジド / 化学合成 / 糖質関連化学・糖鎖工学 / タンパク質化学 / ペプチド化学 / 有機合成化学
Outline of Final Research Achievements

Chemical synthesis is an indispensable technique for the preparation of unique proteins, which cannot be prepared by recombinant technique. In this work, we have developed a new regioselective peptide coupling strategy that enables one-pot peptide ligations. This new technique is based on the unique switchable reactivity of peptide-guanidine, an emerging peptide derivative. As a result, we succeeded in the assembly of full legth of erythropoieitn consisting of 166 amino acids from 4 peptide segments in one-pot manner. Furthermore, we also successfully synthesized a small circular protein by using th new regioselective peptide coupling strategy.

Academic Significance and Societal Importance of the Research Achievements

本研究で開発した技術は、これまで容易ではなかった大型のタンパク質とともに、環状タンパク質などの遺伝子工学では手に入らない特殊な構造のタンパク質合成にも利用可能である。この技術を利用することで、今後様々な人工機能性タンパク質の合成が期待できる。このような分子は天然に存在するタンパク質の機能を凌駕できる可能性を秘めており、基礎研究から創薬などの応用研究を含む広範な生命科学研究に貢献することが期待される。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (8 results)

All 2018 2017

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (7 results) (of which Int'l Joint Research: 5 results,  Invited: 4 results)

  • [Journal Article] Total Synthesis of O-GalNAcylated Antifreeze Glycoprotein using the Switchable Reactivity of Peptidyl-N-pivaloylguanidine2017

    • Author(s)
      Orii Ryo、Sakamoto Noriko、Fukami Daichi、Tsuda Sakae、Izumi Masayuki、Kajihara Yasuhiro、Okamoto Ryo
    • Journal Title

      Chemistry - A European Journal

      Volume: 23 Issue: 39 Pages: 9253-9257

    • DOI

      10.1002/chem.201702243

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] Total Synthesis of O-GalNAcylated Antifreeze Glycoprotein Toward Elucidation of the Functional Role of O-GalNAcylation2018

    • Author(s)
      Ryo Okamoto, Ryo Orii, Daichi Fukami, Sakae Tsuda, Masayuki Izumi, and Yasuhiro Kajihara
    • Organizer
      29th International Carbohydrate Symposium
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Chemical synthesis and functional analysis of antifreeze glycoprotein for elucidation of the function of O-glycosylation2018

    • Author(s)
      Ryo Okamoto
    • Organizer
      Frontiers in peptide science
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemical Synthesis and Functional Analysis of Antifreeze Glycoprotein for Elucidation of the Function of O-Glycosylation2018

    • Author(s)
      Ryo Okamoto
    • Organizer
      Symposium for Stephen B.H.Kent
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 非天然糖タンパク質を合成し天然型糖鎖の機能を探る2018

    • Author(s)
      岡本 亮
    • Organizer
      新学術領域「中分子戦略」「分子夾雑化学」ジョイントシンポジウム 第21回生命化学研究会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] ペプチドピバロイルグアニジド体を用いた新規ワンポットペプチド連結法の開発研究2018

    • Author(s)
      花尾 卓哉、真木 勇太、梶原 康宏、岡本 亮
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] Total Chemical Synthesis of O-GalNAcylated Antifreeze Glycoprotein using the Switchable Reactivity of Peptidyl-N-pivaloylguanidine2017

    • Author(s)
      Ryo Okamoto、Ryo Orii、Daichi Fukami、Sakae Tsuda、Masayuki Izumi、Yasuhiro Kajihara
    • Organizer
      7th Chemical Protein Synthesis Meeting
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Total chemical synthesis of O-GalNAcylated antifreeze glycoprotein using the switchable reactivity of peptidyl-N-pivaloylguanidine2017

    • Author(s)
      Ryo Okamoto
    • Organizer
      6th Modern Solid Phase Peptide Synthesis & its Applications Symposium
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited

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Published: 2016-04-21   Modified: 2020-03-30  

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