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Redefinition of fluorescence-detected circular dichroism for a practical stereo-structure analysis

Research Project

Project/Area Number 16K05696
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionHiroshima University

Principal Investigator

Nehira Tatsuo  広島大学, 総合科学研究科, 准教授 (60321692)

Research Collaborator Ishida Atsuhiko  
Watanabe Masayuki  
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2018: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2016: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Keywords円二色性 / 蛍光 / 絶対配置 / タンパク質 / 立体構造
Outline of Final Research Achievements

Aiming at a practical stereo-structure analysis with fluorescence-detected circular dichroism (FDCD) using our original artifact-free device, revision of FDCD theory and observation mechanism was pursued. It was experimentally found that the FDCD spectra of some organic small molecules were altered from the traditional CD spectra. Supposing that this alternation may be caused from multiple fluorescence paths, theoretical calculations were attempted. For protein FDCD, supposing that an achiral acceptor can report the chirality from donors through fluorescence resonance energy transfer, a naphthalene-based chiral donor and an anthracene-based achiral acceptor were synthesized. Although the absorption and emission properties were good enough, the yield of synthesis was not good. A new model design is required. Through the research, the absolute configurations of some natural organic compounds were determined as collaboration with other research groups.

Academic Significance and Societal Importance of the Research Achievements

分子の立体構造の決定は一般に高コストかつ長時間を要する場合もある。本研究は、分子の立体構造決定の迅速かつ高感度な新しい選択肢を提供しようとするものである。独自開発した装置を手に、研究開始時の目標は測定理論の再構築であったが、研究期間内には実験と理論計算による理論の再構築には至らず、観測メカニズムの解明を狙ったモデル合成は低収率のため再検討を余儀なくされた。なお、研究の過程で培った手技と経験を応用して、他の研究グループとの共同研究としていくつかの新規天然有機化合物の構造決定に貢献した。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (21 results)

All 2018 2017 2016 Other

All Int'l Joint Research (2 results) Journal Article (12 results) (of which Int'l Joint Research: 5 results,  Peer Reviewed: 12 results,  Open Access: 3 results,  Acknowledgement Compliant: 2 results) Presentation (7 results)

  • [Int'l Joint Research] Michigan State University(米国)

    • Related Report
      2017 Research-status Report
  • [Int'l Joint Research] Caraga State University/Mindanao State University(フィリピン)

    • Related Report
      2017 Research-status Report
  • [Journal Article] Sulfated Purine Alkaloid Glycosides from the Pupal Case Built by the Bruchid Beetle Bruchidius dorsalis Inside the Seed of Gleditsia japonica2018

    • Author(s)
      Harauchi Yui、Muranaka Kyo、Ohta Emi、Kawachi Hiroyuki、Imamura-Jinda Aya、Nehira Tatsuo、Omura Hisashi、Ohta Shinji
    • Journal Title

      Chemistry & Biodiversity

      Volume: 15 Issue: 8

    • DOI

      10.1002/cbdv.201800154

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] HPLC profiles and spectroscopic data of cassane-type furanoditerpenoids2018

    • Author(s)
      Akihara Yui、Kamikawa Sayuri、Harauchi Yui、Ohta Emi、Nehira Tatsuo、Omura Hisashi、Ohta Shinji
    • Journal Title

      Data in Brief

      Volume: 21 Pages: 1076-1088

    • DOI

      10.1016/j.dib.2018.10.068

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Two new secondary metabolites from a fungus of the genus Robillarda2018

    • Author(s)
      Shimoyama Takeo、Miyoshi Mizuki、Nehira Tatsuo、Motojima Atsuko、Oikawa Tsutomu、Laurence Olivier、Igarashi Yasuhiro
    • Journal Title

      The Journal of Antibiotics

      Volume: 71 Issue: 4 Pages: 432-437

    • DOI

      10.1038/s41429-017-0015-x

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Computationally Aided Absolute Stereochemical Determination of Enantioenriched Amines2017

    • Author(s)
      Zhang Jun、Gholami Hadi、Ding Xinliang、Chun Minji、Vasileiou Chrysoula、Nehira Tatsuo、Borhan Babak
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 6 Pages: 1362-1365

    • DOI

      10.1021/acs.orglett.7b00246

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Cyclohelminthol X, a Hexa-Substituted Spirocyclopropane from Helminthosporium velutinum yone96: Structural Elucidation, Electronic Circular Dichroism Analysis, and Biological Properties2017

    • Author(s)
      Tanaka Shizuya、Honmura Yuna、Uesugi Shota、Fukushi Eri、Tanaka Kazuaki、Maeda Hayato、Kimura Ken-ichi、Nehira Tatsuo、Hashimoto Masaru
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 11 Pages: 5574-5582

    • DOI

      10.1021/acs.joc.7b00393

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Ficusnotins A-F: Rare diarylbutanoids from the leaves of Ficus nota2017

    • Author(s)
      Latayada Felmer S.、Uy Mylene M.、Akihara Yui、Ohta Emi、Nehira Tatsuo、Omura Hisashi、Ohta Shinji
    • Journal Title

      Phytochemistry

      Volume: 141 Pages: 98-104

    • DOI

      10.1016/j.phytochem.2017.05.016

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] New Prenylated ortho-Dihydroxycoumarins from the Fruits of Ficus nipponica2017

    • Author(s)
      Akihara Yui、Ohta Emi、Nehira Tatsuo、Omura Hisashi、Ohta Shinji
    • Journal Title

      Chemistry & Biodiversity

      Volume: 14 Issue: 9

    • DOI

      10.1002/cbdv.201700196

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Spontaneous emulsification and self-propulsion of oil droplets induced by the synthesis of amino acid-based surfactants2017

    • Author(s)
      Nagasaka Yuriko、Tanaka Shinpei、Nehira Tatsuo、Amimoto Tomoko
    • Journal Title

      Soft Matter

      Volume: 13 Issue: 37 Pages: 6450-6457

    • DOI

      10.1039/c7sm01117b

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] xidative Desulfurization of Electron-Donating 5,5,7,7-Tetraaryl-5,7-dihydrodibenzo[c,e]thiepins and the Related Heterocycles: Generation of Dicationic Dyes upon Two-Electron Oxidation2017

    • Author(s)
      T. Suzuki, T. Kuroda, H. Tamaoki, S. Higasa, T. Nehira, R. Katoono, Y. Ishigaki, K. Fujiwara, T. Fukushima, H. Yamada
    • Journal Title

      Heterocycles

      Volume: 95(2), Issue: 2 Pages: 816-829

    • DOI

      10.3987/com-16-s(s)50

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Crataegusins A and B, new flavanocoumarins from the dried fruits of Crataegus pinnatifida var. major (Rosacea)2016

    • Author(s)
      Kohei Kazuma, Yuka Isobe, Haruka Asahina, Tatsuo Nehira, Motoyoshi Satake, Katsuhiro Konno
    • Journal Title

      Natural Product Communications

      Volume: 11 Pages: 965-969

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Petroquinones: Trimeric and dimeric xestoquinone derivatives isolated from the marine sponge Petrosia alfiani2016

    • Author(s)
      N. Tanokashira, S. Kukita, H. Kato, T. Nehira, E. D. Angkouw, R. E. P. Mangindaan, N. J. de Voogd, S. Tsukamoto
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 35 Pages: 5530-5540

    • DOI

      10.1016/j.tet.2016.07.045

    • NAID

      120006897989

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Nabscessins A and B, new aminocyclitol derivatives from Nocardia abscessus IFM 10029T2016

    • Author(s)
      Shoko Hara, Naoki Ishikawa, Yasumasa Hara, Tatsuo Nehira, Kanae Sakai, Tohru Gonoi, Masami Ishibashi
    • Journal Title

      Journal of Natural Products

      Volume: 80 Issue: 2 Pages: 565-568

    • DOI

      10.1021/acs.jnatprod.6b00935

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Cyclohelmintol XおよびYの構造2018

    • Author(s)
      田中静也,本村優奈,前多隼人,田中和明,木村賢一,上杉祥太,福士江里,根平達夫,橋本勝
    • Organizer
      第60回天然有機化合物討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] ジャケツイバラ種子内に寄生するザウテルマメゾウムシの代謝成分2018

    • Author(s)
      秋原由依,紙川小百合,原内優衣,太田恵美,根平達夫,大村尚,太田伸二
    • Organizer
      第60回天然有機化合物討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 海洋由来新規天然物Dolapyrrolidoneの絶対配置の決定2018

    • Author(s)
      村上綾菜,林純一,井川和宣,堤美葵,友岡克彦,永井宏史,根平達夫
    • Organizer
      日本化学会中国四国支部2018年支部大会(愛媛大会)
    • Related Report
      2018 Annual Research Report
  • [Presentation] マメゾウムシ蛹室由来の新規化学成分の構造と生理活性2017

    • Author(s)
      原内優衣,村中恭,紙川小百合,太田恵美,根平達夫,大村尚,太田伸二
    • Organizer
      第59回天然有機化合物討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] ザウテルマメゾウムシ蛹室由来のフラノジテルペノイド類2016

    • Author(s)
      紙川小百合,太田恵美,根平達夫,大村尚,太田伸二
    • Organizer
      TEAC2016
    • Place of Presentation
      東京
    • Year and Date
      2016-10-29
    • Related Report
      2016 Research-status Report
  • [Presentation] 蛍光検出円二色性(FDCD)を利用した迅速かつ簡便なタンパク質高次構造解析の試み2016

    • Author(s)
      伊藤弘音,根平達夫,石原郁,益田恵子,浮穴和義,松尾光一,泉俊輔,山﨑岳,石田敦彦
    • Organizer
      日本生化学会大会
    • Place of Presentation
      仙台
    • Year and Date
      2016-09-25
    • Related Report
      2016 Research-status Report
  • [Presentation] 蛍光検出円二色性(FDCD)分光法によるタンパク質立体構造解析の試み2016

    • Author(s)
      根平達夫,伊藤弘音,石原郁,益田恵子,浮穴和義,松尾光一,泉俊輔,山﨑岳,石田敦彦
    • Organizer
      第11回化学生態学研究会
    • Place of Presentation
      函館
    • Year and Date
      2016-07-01
    • Related Report
      2016 Research-status Report

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Published: 2016-04-21   Modified: 2022-02-22  

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