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Development and applications of biomimetic peptide synthesis

Research Project

Project/Area Number 18K14396
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 38040:Bioorganic chemistry-related
Research InstitutionKyoto University

Principal Investigator

Kuranaga Takefumi  京都大学, 薬学研究科, 助教 (70625201)

Project Period (FY) 2018-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsペプチド / 生合成 / 有機合成 / 全合成 / 天然物化学
Outline of Final Research Achievements

In this project, the development of a new methodology for the biomimetic peptide synthesis and its applications to the biosynthetic studies on the structurally unique peptidic natural products were achieved. The new methodology has been efficiently utilized in the biosynthetic studies on the peptidic natural products, namely, cyclic peptides surugamides A-E, a linear peptide surugamide F, and a hybrid peptide-polyketide natural product kasumigamide.
In addition to this, the complete structural determination of the new peptiditic natural products,thioamycolamides A-E, were also accomplished by the chemical syntheses program in this project.

Academic Significance and Societal Importance of the Research Achievements

本研究は学術界・産業界いずれでも当然のように文字通り「不自然」な向きにペプチド鎖が伸長されている現在の化学合成を一新しうる重大な意義を持つ研究である。また現代における未知の生合成酵素メカニズム解明は、遺伝子操作や配列相同性検索などから芋づる式に未知の天然物の発見を導く。そのため本研究は化学合成を足がかりとした生合成メカニズム解明研究から、新規有用生物活性化合物(新規創薬リード)探索研究としての展開・社会への貢献が期待される研究でもある。

Report

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

    (15 results)

All 2023 2020 2019 2018

All Journal Article (8 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 8 results,  Open Access: 1 results) Presentation (5 results) (of which Int'l Joint Research: 1 results,  Invited: 3 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Thioamycolamides A-E, Sulfur-Containing Cycliclipopeptides Produced by the Rare Actinomycete Amycolatopsis sp.2020

    • Author(s)
      Chengqian Pan, Takefumi Kuranaga, Chao Liu, Shan Lu, Naoya Shinzato, Hideaki Kakeya
    • Journal Title

      Org. Lett.

      Volume: 22 Issue: 8 Pages: 3014-3017

    • DOI

      10.1021/acs.orglett.0c00776

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A New Cyclase Family Catalyzing Head-to-Tail Macrolactamization of Non-ribosomal Peptides2019

    • Author(s)
      Matsuda Kenichi、Kuranaga Takefumi、Wakimoto Toshiyuki
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 77 Issue: 11 Pages: 1106-1115

    • DOI

      10.5059/yukigoseikyokaishi.77.1106

    • NAID

      130007742538

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2019-11-01
    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The Revised Structure of the Cyclic Octapeptide Surugamide A2019

    • Author(s)
      Matsuda Kenichi、Kuranaga Takefumi、Sano Ayae、Ninomiya Akihiro、Takada Kentaro、Wakimoto Toshiyuki
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 67 Issue: 5 Pages: 476-480

    • DOI

      10.1248/cpb.c19-00002

    • NAID

      130007641158

    • ISSN
      0009-2363, 1347-5223
    • Year and Date
      2019-05-01
    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] ペニシリン結合タンパク質によるペプチド環化2019

    • Author(s)
      松田 研一、倉永 健史、脇本 敏幸
    • Journal Title

      Farumashia

      Volume: 55 Issue: 7 Pages: 650-654

    • DOI

      10.14894/faruawpsj.55.7_650

    • NAID

      130007671605

    • ISSN
      0014-8601, 2189-7026
    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Scrobiculosides A and B from the deep-sea sponge Pachastrella scrobiculosa2019

    • Author(s)
      Jomori Takahiro、Ise Yuji、Kohtsuka Hisanori、Matsuda Kenichi、Kuranaga Takefumi、Wakimoto Toshiyuki
    • Journal Title

      Journal of Natural Medicine

      Volume: 73 Issue: 4 Pages: 1058-1061

    • DOI

      10.1007/s11418-019-01315-6

    • NAID

      40021995195

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Introduction of D-Amino Acids in Minimalistic Peptide Substrates by an S-Adenosyl-L-Methionine Radical Epimerase2019

    • Author(s)
      Anna L. Vagstad, Takefumi Kuranaga, Salome Puentener, Vijay Pattabiraman, Jeffrey W. Bode, Joern Piel
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 58 Issue: 8 Pages: 2246-2250

    • DOI

      10.1002/anie.201809508

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] SurE is a trans-acting thioesterase cyclizing two distinct non-ribosomal peptides2019

    • Author(s)
      Matsuda, K., Kobayashi, M., Kuranaga, T., Takagda, K., Ikeda, H., Matsunaga, S., Wakimoto, T.,
    • Journal Title

      Org. Biomol. Chem.

      Volume: 17 Issue: 5 Pages: 1058-1061

    • DOI

      10.1039/c8ob02867b

    • Related Report
      2019 Annual Research Report 2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Total Synthesis of the Nonribosomal Peptide Surugamide?B and Identification of a New Offloading Cyclase Family2018

    • Author(s)
      Kuranaga Takefumi、Matsuda Kenichi、Sano Ayae、Kobayashi Masakazu、Ninomiya Akihiro、Takada Kentaro、Matsunaga Shigeki、Wakimoto Toshiyuki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 57 Issue: 30 Pages: 9447-9451

    • DOI

      10.1002/anie.201805541

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] 実用的inverseペプチド合成法の開発2020

    • Author(s)
      森本涼太, 倉永健史, 脇本敏幸, 掛谷秀昭
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Chemical Synthesis and Biosynthesis of Peptidic Natural Products2020

    • Author(s)
      Takefumi Kuranaga
    • Organizer
      日本化学会第100春季年会「若い世代の特別講演」
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] 田地川千里1, 松田研一2, 倉永健史3,脇本敏幸22019

    • Author(s)
      スルガミド環化酵素SurEによる環状カスミガミドの合成
    • Organizer
      第8回食品薬学シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] ものとり指向型化学合成2019

    • Author(s)
      倉永健史
    • Organizer
      第54回天然物化学談話会(受賞講演)
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Chemical Synthesis and Biosynthesis of Scarce Natural Products2018

    • Author(s)
      Takefumi Kuranaga
    • Organizer
      International Congress on Pure & Applied Chemistry Langkawi (ICPAC Langkawi)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Patent(Industrial Property Rights)] 新規フルオロジニトロフェニル化合物及びその用途2023

    • Inventor(s)
      掛谷秀昭, 倉永健史, 小川はるか
    • Industrial Property Rights Holder
      国立大学法人京都大学
    • Industrial Property Rights Type
      特許
    • Acquisition Date
      2023
    • Related Report
      Products Report
  • [Patent(Industrial Property Rights)] 新規フルオロジニトロフェニル化合物及びその用途2019

    • Inventor(s)
      掛谷秀昭, 倉永健史, 小川はるか
    • Industrial Property Rights Holder
      国立大学法人京都大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2019-081766
    • Filing Date
      2019
    • Related Report
      Products Report

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Published: 2018-04-23   Modified: 2025-03-27  

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