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Green synthesis of oligopeptides in the inverse direction by a novel, thiol-relay method

Research Project

Project/Area Number 26810062
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionToho University

Principal Investigator

SASAKI Kaname  東邦大学, 理学部, 講師 (10611783)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2016: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywordsペプチド合成 / グリーン合成 / アミド結合形成 / チオカルボン酸 / 環状炭酸無水物 / 高原子効率 / グリーンケミストリー
Outline of Final Research Achievements

The most reliable and generally used method for preparation of oligopeptides is currently solid-supported synthesis, which requires excess monomers, excess dehydrating agents and protective group manipulations. We consider this classical method to be updated to circumvent its low atom economy, and design a novel method named ‘thiol-relay,’ which discharges only carbon dioxide along with construction of a peptide bond. First, we improved an access to the thiocarboxylic acid, a key function in thiol-relay method, by introducing a novel, easy-to-prepare, and easy-to-handle precursor. The basic concept of thiol-relay peptide synthesis was proven, and we also found some problems toward more practical use of this method.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (2 results)

All 2016

All Journal Article (1 results) (of which Peer Reviewed: 1 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (1 results)

  • [Journal Article] α-Methylphenacyl thioesters as convenient thioacid precursors2016

    • Author(s)
      Toru Hatanaka, Ryosuke Yuki, Ryota Saito, Kaname Sasaki
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 14 Issue: 45 Pages: 10589-10592

    • DOI

      10.1039/c6ob02256a

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] Boc基と直交するチオカルボン酸前駆体の開発2016

    • Author(s)
      畑中 徹・結城 亮介・齋藤 良太・佐々木 要
    • 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
      2016-03-25
    • Related Report
      2015 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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