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

Biomimetic iterative method for polyketide synthesis

Research Project

Project/Area Number 17K05854
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

Akagawa Kengo  東京大学, 生産技術研究所, 助教 (60548733)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2019: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2018: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2017: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Keywordsポリケチド / 繰り返し合成 / 固相合成 / マロン酸ハーフチオエステル / 含フッ素ポリケチド / 生体模倣合成 / 繰り返し反応 / β-ケトチオエステル / α-フルオロマロン酸 / 有機化学
Outline of Final Research Achievements

Polyketides constitute a class of compounds with a wide variety of structures and oxidation states. Despite the diversity of polyketide molecules, they are synthesized via the common iterative process in nature. By mimicking the biological system, we established the iterative synthetic method for affording various types of polyketides. Chain elongation of a carboxylic acid with malonic acid half thioester was used as the key reaction for the iterative synthesis. It was shown that different types of polyketides could be synthesized by repeating a few kinds of reactions. The iterative method was extended to the solid-phase synthesis for obtaining polyketides with simple operations.

Academic Significance and Societal Importance of the Research Achievements

ポリケチドは医薬品開発の基礎となる重要な化合物群であり、本研究では繰り返し反応によるポリケチド合成が可能な手法を開発した。異なる種類の天然ポリケチドを統一的な手段で合成できることに加え、フッ素や窒素原子を任意の位置に導入した非天然型のポリケチド合成も可能である。簡便な操作の繰り返しで多種類のポリケチド化合物が得られるため、本法を利用した新たな医薬品の創製が期待できる。

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • 2017 Research-status Report
  • Research Products

    (16 results)

All 2020 2019 2018 2017

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (10 results) Book (1 results)

  • [Journal Article] Design of Peptide Catalysts by Combining Secondary Structural Units for Selective Reactions2019

    • Author(s)
      赤川賢吾, 工藤一秋
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 77 Issue: 12 Pages: 1222-1233

    • DOI

      10.5059/yukigoseikyokaishi.77.1222

    • NAID

      130007760865

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2019-12-01
    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Kinetic Resolution of Ansa Cyclophanes by Peptide-Catalyzed Aldol/Retro-Aldol Reactions2018

    • Author(s)
      Kengo Akagawa, Junichi Higuchi, Isao Yoshikawa, Kazuaki Kudo
    • Journal Title

      European Jornal of Organic Chemistry

      Volume: - Issue: 38 Pages: 5278-5281

    • DOI

      10.1002/ejoc.201800774

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Iterative Polyketide Synthesis via a Consecutive Carbonyl-Protecting Strategy2018

    • Author(s)
      Kengo Akagawa, Kazuaki Kudo
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 83 Pages: 4279-4285

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Biomimetic iterative method for polyketide synthesis2017

    • Author(s)
      Kengo Akagawa, Kazuaki Kudo
    • Journal Title

      Chemical Communications

      Volume: 53 Issue: 62 Pages: 8645-8648

    • DOI

      10.1039/c7cc04033d

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Development of Selective Peptide Catalysts with Secondary Structural Frameworks2017

    • Author(s)
      Kengo Akagawa, Kazuaki Kudo
    • Journal Title

      Accounts of Chemical Research

      Volume: 50 Issue: 10 Pages: 2429-2439

    • DOI

      10.1021/acs.accounts.7b00211

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] フルオロマロン酸ユニットを用いた炭素鎖伸長反応と含フッ素ポリケチド合成への応用2020

    • Author(s)
      頼近光昭, 赤川賢吾, 工藤一秋
    • Organizer
      日本化学会 第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Facile substitution reaction of guaiazulene-3-methanol derivatives with thiols and its application to labelling of thiol-containing biomolecules2020

    • Author(s)
      Yu Jin, Kengo Akagawa, Kazuaki Kudo
    • Organizer
      日本化学会 第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Synthesis of 2-trifluoromethyl-substituted five membered N-heterocyclic compounds via decarboxylative [3+2] cycloaddition2020

    • Author(s)
      Qian Liu, Kengo Akagawa, Kazuaki Kudo
    • Organizer
      日本化学会 第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] N末端グアニジル化ペプチド触媒を用いた不斉マイケル付加反応2020

    • Author(s)
      溜渕堅也, 赤川賢吾, 工藤一秋
    • Organizer
      日本化学会 第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 生合成機構を模倣したポリケチドの固相合成法の開発2019

    • Author(s)
      竹内優太、赤川賢吾、工藤一秋
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] フルオロマロン酸ユニットを用いた含フッ素ポリケチドの繰り返し合成2019

    • Author(s)
      頼近光昭、赤川賢吾、工藤一秋
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Facile blue-color labelling of biomolecules under mild conditions using guaiazulene-derived alcohol2019

    • Author(s)
      Yu Jin, Kengo Akagawa, Kazuaki Kudo
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 生合成機構を模倣したポリケチドの固相合成法の開発2018

    • Author(s)
      竹内優太、赤川賢吾、工藤一秋
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 固相担持ペプチド触媒を用いた面不斉[n]パラシクロファンの速度論的光学分割2018

    • Author(s)
      樋口淳一、赤川賢吾、工藤一秋
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] Development of Tandem Enantioselective Intramolecular Rauhut Currier Reaction and Aldol Condensation Promoted by Peptide Catalyst2018

    • Author(s)
      YINGQI Tian, Zhaonan Du, Kengo Akagawa, Kazuaki Kudo
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Book] Peptide Applications in Biomedicine, Biotechnology and Bioengineering, chapter 192017

    • Author(s)
      Edited by Sotirios Koutsopoulos
    • Total Pages
      52
    • Publisher
      Woodhead Publishing
    • ISBN
      9780081007365
    • Related Report
      2017 Research-status Report

URL: 

Published: 2017-04-28   Modified: 2021-02-19  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi