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Bioinspired synthesis and structural elucidation of natural naphthoquinone dimers

Research Project

Project/Area Number 25850083
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Bioorganic chemistry
Research InstitutionKyoto Prefectural University

Principal Investigator

KURAMOCHI Kouji  京都府立大学, 生命環境科学研究科(系), 准教授 (90408708)

Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2014: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2013: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Keywords天然物合成 / 生合成模倣 / 1,4-ナフトキノン / 二量化 / 絶対立体配置 / 全合成 / 天然物 / ナフトキノン
Outline of Final Research Achievements

Juglorubin, which was isolated from Streptomyces sp., is a red ionic dye. It has been proposed that the biosynthetic pathway to juglorubin might include dimerization of juglomycin C and formation of juglocombin A as a key biosynthetic intermediate. The relative configuration of juglorubin has been determined by X-ray crystallography. However, the absolute configuration of this compound as well as juglocombin A still remains unknown. The aims of this research are 1) total synthesis of natural 1,4-naphthoquinone dimers based on the plausible biogenetic pathway, 2) determination of the absolute configuration of these compounds.

Report

(3 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • Research Products

    (15 results)

All 2015 2014 2013 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 2 results) Presentation (11 results) (of which Invited: 1 results) Remarks (1 results)

  • [Journal Article] Synthesis and Structural Characterization of Natural Benzofuranoids2015

    • Author(s)
      Kouji Kuramochi, Kazunori Tsubaki
    • Journal Title

      Journal of Natural Products

      Volume: 78 Issue: 5 Pages: 1056-1066

    • DOI

      10.1021/np5010483

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of enantiomerically pure juglomycin C and NHAB2015

    • Author(s)
      Shogo Kamo, Sayako Maruo, Kouji Kuramochi, Kazunori Tsubaki
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 21 Pages: 3478-3484

    • DOI

      10.1016/j.tet.2015.03.073

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Dimerization Reactions of 2-Bromo-3,5,6-trimethyl-1,4-benzoquinone2013

    • Author(s)
      Shuhei Azuma, Motohiro Ota, Akito Ishida, Katsuhiro Isozaki, Hikaru Takaya, Masaharu Nakamura, Takahiro Sasamori, Norihiro Tokitoh, Kouji Kuramochi, Kazunori Tsubaki
    • Journal Title

      Chemistry Letters

      Volume: 42 Issue: 12 Pages: 1531-1533

    • DOI

      10.1246/cl.130781

    • NAID

      130004867845

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 天然ベンゾフラノイド類の網羅的合成2015

    • Author(s)
      倉持 幸司、椿 一典
    • Organizer
      日本農芸化学会2015年会(岡山)
    • Place of Presentation
      岡山大学
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] Juglorubin 及び関連天然物の合成研究2015

    • Author(s)
      加茂 翔伍、倉持 幸司、椿 一典
    • Organizer
      日本農芸化学会2015年会(岡山)
    • Place of Presentation
      岡山大学
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 1,4-ナフトキノン二量化反応による機能性分子の創成2015

    • Author(s)
      太田 元博、倉持 幸司、椿 一典
    • Organizer
      日本農芸化学会2015年会(岡山)
    • Place of Presentation
      岡山大学
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 1,4-ナフトキノンの二量化反応を用いた Juglorubin 類の合成研究2014

    • Author(s)
      加茂翔伍、倉持幸司、椿一典
    • Organizer
      第64回 日本薬学会近畿支部総会・大会
    • Place of Presentation
      京都薬科大学
    • Year and Date
      2014-10-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] 三環性天然ベンゾフラノイドの網羅的合成2014

    • Author(s)
      倉持幸司、椿一典
    • Organizer
      日本農芸化学会関西支部大会 (関西支部80周年記念大会)
    • Place of Presentation
      奈良先端科学技術大学院大学
    • Year and Date
      2014-09-20
    • Related Report
      2014 Annual Research Report
  • [Presentation] キノン二量化反応による機能性分子の創成2014

    • Author(s)
      太田元博、笹森貴裕、時任宣博、倉持幸司、椿一典
    • Organizer
      日本農芸化学会関西支部大会 (関西支部80周年記念大会)
    • Place of Presentation
      奈良先端科学技術大学院大学
    • Year and Date
      2014-09-20
    • Related Report
      2014 Annual Research Report
  • [Presentation] 1,4-ナフトキノン類の二量化反応を用いた Juglorubin 及び関連天然物の合成研究2014

    • Author(s)
      加茂翔伍、倉持幸司、椿一典
    • Organizer
      第34回 有機合成若手セミナー 明日の有機合成を担う人のために
    • Place of Presentation
      大阪大学
    • Year and Date
      2014-08-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] キノン二量化反応による2H-クロメンの合成とさらなる光二量化反応2014

    • Author(s)
      太田元博、笹森貴裕、水品善之、時任宣博、倉持幸司、椿一典
    • Organizer
      日本農芸化学会 関西支部 第484回講演会
    • Place of Presentation
      京都府立大学
    • Year and Date
      2014-05-24
    • Related Report
      2014 Annual Research Report
  • [Presentation] キノンの二量化を基軸とした有用化合物の合成研究2013

    • Author(s)
      倉持 幸司
    • Organizer
      第 28 回農薬デザイン研究会
    • Place of Presentation
      京都メルパルク
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Biomimetic Synthesis of Zeylanone and Zeylanone Epoxide by Dimerization of 2-Methyl-1,4-naphthoquinone2013

    • Author(s)
      Kouji Kuramochi, Sayako Maruo, Kazuyuki Nishio, Kazunori Tsubaki
    • Organizer
      43rd National Organic Chemistry Symposium
    • Place of Presentation
      University of Washington
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of Zeylanone and Zeylanone Epoxide by Biomimetic Anionic Dimerization of Plumbagin2013

    • Author(s)
      Sayako Maruo, Kazuyuki Nishio, Kouji Kuramochi, Kazunori Tsubaki
    • Organizer
      10th International Symposium on Carbanion Chemistry
    • Place of Presentation
      Doshisha University
    • Related Report
      2013 Research-status Report
  • [Remarks] 機能分子合成化学研究室ホームページ

    • URL

      http://www2.kpu.ac.jp/life_environ/syn_chem_fm/index.htm

    • Related Report
      2014 Annual Research Report

URL: 

Published: 2014-07-25   Modified: 2019-07-29  

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