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Development of Innovative Peptide Synthetic Method by Dehydrative Condensation Catalysis

Research Project

Project/Area Number 15K13692
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

Ishihara Kazuaki  名古屋大学, 工学(系)研究科(研究院), 教授 (40221759)

Project Period (FY) 2015-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Keywordsアミド縮合 / ボロン酸 / ペプチド / カルボン酸 / 脱水縮合 / 触媒 / グリーンケミストリー / 酸塩基複合化学 / DMAPO / アミン / 協奏触媒 / 酸塩基触媒 / アミド
Outline of Final Research Achievements

Dehydrtaive condensation reaction between equimolar amounts of carboxylic acids and amines is the most ideal synthetic method of amides and peptides. Several arylboronic acids have already been reported effective as catalysts for this condensation reaction. Here we found that 2,4-bis(trifluoromethyl)phenylboronic acid was much more effective than arylboronic acids known as catalysts. It is noted that ortho-trifluoromethyl group of 2,4-bis(trifluoromethyl)phenylboronic acid is important to increase the catalytic activity. ortho-Trifluoromethyl group played important roles as not only electron-withdrawing group but also sterically bulky group. This steric bulkiness suppressed the generation of inert species via boronic acid and amines.

Report

(2 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • Research Products

    (6 results)

All 2016 2015

All Journal Article (1 results) (of which Peer Reviewed: 1 results,  Acknowledgement Compliant: 1 results) Presentation (5 results) (of which Invited: 2 results)

  • [Journal Article] Boronic Acid–DMAPO Cooperative Catalysis for Dehydrative Condensation between Carboxylic Acids and Amines2016

    • Author(s)
      Kazuaki Ishihara and Yanhui Lu
    • Journal Title

      Chem. Sci.

      Volume: 7 Issue: 2 Pages: 1276-1280

    • DOI

      10.1039/c5sc03761a

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Novel Boronic Acid-catalyzed Amide Condensation Reaction2016

    • Author(s)
      Ke WANG, Yanhui LU, Kazuaki ISHIHARA
    • Organizer
      日本化学会第96春季年会(2016)
    • Place of Presentation
      同志社大学 京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 第二級アミン-ボロン酸協奏型触媒を用いるα,β,γ,δ-不飽和カルボン酸とケトンの[4+2]脱水環化付加反応2016

    • Author(s)
      中田裕斗、魯彦会、堀部貴大、石原一彰
    • Organizer
      日本化学会第96春季年会(2016)
    • Place of Presentation
      同志社大学 京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] エステル・アミド縮合触媒の開発2016

    • Author(s)
      石原一彰
    • Organizer
      第5回慶應義塾大学戦略的研究基盤形成支援事業シンポジウム 有機合成化学ー効率化と環境調和性ー
    • Place of Presentation
      慶應義塾大学矢上キャンパス
    • Year and Date
      2016-03-14
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Boronic acid-DMAPO cooperative catalysis for dehydrative condensation of carboxylic acids with amines2015

    • Author(s)
      Kazuaki Ishihara, Yanhui Lu
    • Organizer
      Pacifchem 2015
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Boronic Acid–DMAPO Cooperative Catalysis for Dehydrative Condensation between Carboxylic Acids and Amines2015

    • Author(s)
      Yanhui Lu, Kazuaki Ishihara
    • Organizer
      The 5th Junior International Conference on Cutting-edge Organic Chemistry in Asia (Junior ICCEOCA-5)
    • Place of Presentation
      Taiwan
    • Year and Date
      2015-10-30
    • Related Report
      2015 Annual Research Report

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Published: 2015-04-16   Modified: 2017-05-10  

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