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Synthetic study of antibiotic cyclopeptides toward eluciation of structure-activity relationships

Research Project

Project/Area Number 15K01796
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Biomolecular chemistry
Research InstitutionTohoku University

Principal Investigator

Yoshida Masahito  東北大学, 薬学研究科, 助教 (80511906)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords環状ペプチド / 抗菌活性 / 全合成 / 構造活性相関 / ピペラジン酸
Outline of Final Research Achievements

In this research, total synthesis of potent antibiotic cyclodepsipeptide piperidamycins was investigated. Originally developed Sc(OTf)3-catalyzed acylation of gamma-hydroxypiperazic acid derivative with piperazic chloride afforded the corresponding dipeptide, which was sequentially coupled with piperazic chlorides to provide desired tetrapiperazic acid derivative. After elongation to the hexapeptide by condensation with corresponding amino acids, removal of the protecting groups at N- and C-terminus afforded the cyclization precursor. Finally, macrolactonization using MNBA/DMAPO under high dilution conditions, followed by global deprotection of the protecting groups furnished plausible structure of piperidamycin F.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (10 results)

All 2018 2017 2016 2015 Other

All Presentation (9 results) (of which Int'l Joint Research: 1 results,  Invited: 4 results) Remarks (1 results)

  • [Presentation] Synthetic Study for Antibiotic Cyclodepsipeptide Piperidamycins2018

    • Author(s)
      Masahito Yoshida
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 生物活性天然環状ペプチドの全合成を基盤とした構造活性相関研究から分子プローブ創製へ2018

    • Author(s)
      吉田将人
    • Organizer
      Asian Chemical Probe Research Hub Symposium
    • Related Report
      2017 Annual Research Report
  • [Presentation] Piperidamycin F誘導体の合成研究2017

    • Author(s)
      吉田将人,高橋優輔,関岡直樹,新家一男,土井隆行
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学
    • Year and Date
      2017-03-27
    • Related Report
      2016 Research-status Report
  • [Presentation] 機能解明に向けた生物活性環状ペプチド類の全合成を基盤とする構造活性相関研究2017

    • Author(s)
      吉田将人
    • Organizer
      日本薬学会第137年会 シンポジウム「有機合成化学の若い力」
    • Place of Presentation
      東北大学
    • Year and Date
      2017-03-25
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] 新規抗菌活性天然物Piperidamycin Fの全合成研究2017

    • Author(s)
      吉田将人,高橋優輔,関岡直樹,新家一男,土井隆行
    • Organizer
      第56回日本薬学会東北支部大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Total Synthesis and Biological Evaluation of Biologically Active Cyclodepsipeptides2017

    • Author(s)
      Masahito Yoshida
    • Organizer
      21th Korean Peptide Protein Society Sympodium
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Total Synthesis and Biological Evaluation of Naturally Occurring Middle-size Cyclodepsipeptides Toward elucidation of the Mode of Action2016

    • Author(s)
      Masahito Yoshida
    • Organizer
      第53回ペプチド討論会
    • Place of Presentation
      京都テルサ
    • Year and Date
      2016-10-28
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] Synthetic Study for Piperidamycins2016

    • Author(s)
      吉田将人,高橋優輔,関岡直樹,新家一男,土井隆行
    • Organizer
      平成28年度化学系学協会東北大会
    • Place of Presentation
      いわき明星大学
    • Year and Date
      2016-09-10
    • Related Report
      2016 Research-status Report
  • [Presentation] 特異な生物活性を示す天然物の全合成と作用機構解明に向けた研究2015

    • Author(s)
      吉田将人
    • Organizer
      第3回慶応有機化学若手シンポジウム
    • Place of Presentation
      慶応義塾大学
    • Year and Date
      2015-05-09
    • Related Report
      2015 Research-status Report
    • Invited
  • [Remarks]

    • URL

      http://www.pharm.tohoku.ac.jp/~hannou/index.html

    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2020-03-30  

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