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Total synthesis of natural products with potent cytotoxicity and unique structures directed toward their chemical biologicl studies.

Research Project

Project/Area Number 26292056
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Bioorganic chemistry
Research InstitutionTohoku University

Principal Investigator

Kuwahara Shigefumi  東北大学, (連合)農学研究科(研究院), 教授 (30170145)

Co-Investigator(Kenkyū-buntansha) 清田 洋正  岡山大学, その他の研究科, 教授 (30234397)
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥16,510,000 (Direct Cost: ¥12,700,000、Indirect Cost: ¥3,810,000)
Fiscal Year 2016: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2015: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2014: ¥6,890,000 (Direct Cost: ¥5,300,000、Indirect Cost: ¥1,590,000)
Keywordsamphidinolide / nigricanoside / total synthesis / oxylipin / cytotoxic / 生体分子 / 生理活性 / 有機化学 / 癌 / 細胞毒性 / オキシリピン / マクロライド
Outline of Final Research Achievements

Total synthetic studies on two potent cytotoxicns, amphidinolide N and nigricanoside A) were conducted with the intention of promoting their chemical biological studies. The synthesis of the C17-C29 fragment of the former natural product was accomplished by developing an efficient one-pot THF ring-forming processs. The southeastern segment of the latter was also prepared by exploiting the Evans asymmetric alkylation as a key step. The total synthesis of two natural oxylipins, the structures of which are similar to the oxylipin units incorporated in nigricanoside A, were also achieved and provided some important information useful for the total synthesis of nigricanoside A.

Report

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

    (6 results)

All 2017 2016 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Acknowledgement Compliant: 2 results) Presentation (3 results) Remarks (1 results)

  • [Journal Article] Synthesis of the (9R,13R)-isomer of LDS1, a flower-inducing oxylipin isolated from Lemna paucicostata2016

    • Author(s)
      Yuki Takayasu, Yusuke Ogura, Ryo Towada, Shigefumi Kuwahara,
    • Journal Title

      Bioscience, Biotechnology, and Biochemistry

      Volume: 80 Issue: 8 Pages: 1459-1463

    • DOI

      10.1080/09168451.2016.1166935

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Stereoselective syntehsis of the C17-C29 fragment of amphidinolide N2016

    • Author(s)
      Yuki Fujishima, Yusuke Ogura, Ryo Towada, Masaru Enomoto, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron Letters

      Volume: 57 Issue: 47 Pages: 5240-5242

    • DOI

      10.1016/j.tetlet.2016.10.038

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Sacrolide A の全合成2017

    • Author(s)
      毛利朋世,十和田諒,小倉由資,桑原重文
    • Organizer
      日本農芸化学会2017年度大会
    • Place of Presentation
      京都女子大学(京都府京都市東山区)
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] Amphidinolide NのC17-C29フラグメントの合成研究2016

    • Author(s)
      藤島悠記,福山圭,小倉由資,桑原重文
    • Organizer
      日本農芸化学会2016年度大会
    • Place of Presentation
      札幌コンベンションセンター(北海道札幌市)
    • Year and Date
      2016-03-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] 細胞毒性および抗菌,抗真菌活性を有するSacrolide Aの全合成研究2016

    • Author(s)
      毛利朋世,十和田諒,桑原重文
    • Organizer
      日本農芸化学会東北支部第151回大会
    • Place of Presentation
      山形大学農学部(山形県鶴岡市)
    • Related Report
      2016 Annual Research Report
  • [Remarks] 生物有機化学分野ホームページ

    • URL

      http://www.agri.tohoku.ac.jp/yuuki/abc/Top.html

    • Related Report
      2014 Annual Research Report

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

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