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Creation of light-harvesting carotenoids toward elucidation of the mechanism of the initial process of marine photosynthesis

Research Project

Project/Area Number 17K05935
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Bio-related chemistry
Research InstitutionOsaka City University

Principal Investigator

Sakaguchi Kazuhiko  大阪市立大学, 大学院理学研究科, 准教授 (80264795)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsフコキサンチン / パラセントロン / アレン / カロテノイド / 光合成 / エネルギー伝達 / クロスカップリング / C5ジエン / 19-ヘキサノイルオキシパラセントロン / 両官能性ジエン / 光合成初期過程 / 超効率的エネルギー伝達 / ICT準位 / 多官能性カロテノイド / ペリジニン / 海洋光合成初期過程 / 超分子複合体 / デオキシペリジニン / 海洋光合成
Outline of Final Research Achievements

In order to elucidate the super-efficient energy transfer mechanism in the initial process of marine photosynthesis, we worked on the creation of fucoxanthin analogs. Fucoxanthin is structurally characterized by having a polyene skeleton in which a carbonyl group and an allene are conjugated. As a result, we achieved the following 1-3. 1) Development of conjugated polyene formation method using cross-coupling of bifunctional C5 diene building blocks, 2) Total synthesis of paracentrone with conjugated polyene skeleton similar to fucoxanthin and its improved synthesis, 3) Synthesis of 19-hexanoyloxyparacentrone. We also demonstrated that the Hiyama coupling reaction could be introduced into the newly developed conjugated polyene formation method.

Academic Significance and Societal Importance of the Research Achievements

未だ明らかとなっていない「新奇な励起エネルギー準位(ICT準位)と超効率的な光合成エネルギー伝達の関係」を新規物質の創製により実験的に解明する点に本研究の学術的意義がある。また、社会的意義として、本研究は、次世代エネルギー開発のための基礎研究と位置づけられ、その成果は、未だ実現されていない人工光合成システムの鍵となる光捕集アンテナ系の構築に貢献する。

Report

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

    (15 results)

All 2020 2019 2018 2017

All Journal Article (5 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 5 results,  Acknowledgement Compliant: 3 results) Presentation (10 results) (of which Int'l Joint Research: 4 results)

  • [Journal Article] Acid-catalyzed chirality-transferring intramolecular Friedel–Crafts cyclization of α-hydroxy-α-alkenylsilanes2019

    • Author(s)
      K. Sakaguchi, S. Kubota, W. Akagi, N. Ikeda, M. Higashino, S. Ariyoshi, T. Shinada, Y. Ohfune, T. Nishimura
    • Journal Title

      Chem. Commun.

      Volume: 55 Issue: 59 Pages: 8635-8638

    • DOI

      10.1039/c9cc03509e

    • NAID

      120006879256

    • URL

      https://ocu-omu.repo.nii.ac.jp/records/2019717

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled Synthesis of 19’-Deoxyperidinin2018

    • Author(s)
      N. Kinashi, S. Katsumura, T. Shinada, K. Sakaguchi
    • Journal Title

      Org. Lett.

      Volume: 20 Issue: 3 Pages: 582-585

    • DOI

      10.1021/acs.orglett.7b03695

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled Synthesis of Paracentrone2017

    • Author(s)
      Y. Nishioka, Y. Yano, N. Kinashi, N. Oku, Y. Toriyama, S. Katsumura, T. Shinada, K. Sakaguchi
    • Journal Title

      Synlett

      Volume: 28 Issue: 03 Pages: 327-332

    • DOI

      10.1055/s-0036-1588906

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Strategies to enhance the excitation energy-transfer efficiency in the light-harvesting system using the intra-molecular charge transfer character of carotenoids2017

    • Author(s)
      N. Yukihira, Y. Sugai, M. Fujiwara, D. Kosumi, M. Iha, K. Sakaguchi, S. Katsumura, A.T. Gardiner, R.J. Cogdell, H. Hashimoto
    • Journal Title

      Faraday Discuss.

      Volume: 未確定 Pages: 59-71

    • DOI

      10.1039/c6fd00211k

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Excited state properties of beta-carotene analogs incorporating a lactone ring2017

    • Author(s)
      D. Kosumi, T. Kajikawa, K. Sakaguchi, S. Katsumura, H. Hashimoto
    • Journal Title

      Phys. Chem. Chem. Phys.

      Volume: 19 Issue: 4 Pages: 3000-3009

    • DOI

      10.1039/c6cp06828f

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] β-シリル-γ-アルキリデン-γ-ブチロラクトンとアルデヒドおよびケトンとの立体選択的環化反応2020

    • Author(s)
      有吉 将馬・坂口 和彦・西村 貴洋
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] β-シリル-γ-エチリデン-γ-ブチロラクトンを用いた四置換テトラヒドロピラノンの立体選択的合成2019

    • Author(s)
      有吉将馬、坂口和彦、西村貴洋
    • Organizer
      第39回有機合成若手セミナー
    • Related Report
      2019 Annual Research Report
  • [Presentation] Synthesis of Polyfunctional Carotenoid by Cross-Coupling Strategy2019

    • Author(s)
      K. Sakaguchi, Y. Nishioka, N. Kinashi, T. Shinada, T. Nishimura, H. Hashimoto, S. Katsumura
    • Organizer
      20th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 20)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Acid-Catalyzed Chirality-Transferring Intramolecular Friedel-Crafts Reaction of α-Hydroxy-α-alkenylsilanes2019

    • Author(s)
      S. Kubota, W. Akagi, N. Ikeda, M. Higashino, T. Shinada, Y. Ohfune, T. Nishimura, K. Sakaguchi
    • Organizer
      The 10th OCARINA International Symposium
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] β-シリル-γ-エチリデン-γ-ブチロラクトンを用いた四置換テトラヒドロピラノンの合成2019

    • Author(s)
      有吉将馬、坂口和彦、西村貴洋
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 酸触媒によるα-ヒドロキシ-α-アルケニルシランの分子内Friedel-Crafts反応における不斉転写2018

    • Author(s)
      久保田駿一、赤木航、池田直子、東野勝人、品田哲郎、大船泰史、西村貴洋、坂口和彦
    • Organizer
      第38回有機合成若手セミナー
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis of Polyfunctional Carotenoids via Cross-Coupling Strategy2018

    • Author(s)
      K. Sakaguchi, Y. Nishioka, N. Kinashi, T. Shinada, T. Nishimura, H. Hashimoto, S. Katsumura
    • Organizer
      The 22th International Conference on Organic Synthesis (22-ICOS)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Polyfunctional Carotenoid Synthesis via Cross-Coupling Strategy2018

    • Author(s)
      K. Sakaguchi, Y. Nishioka, N. Kinashi, T. Shinada, T. Nishimura, H. Hashimoto, S. Katsumura
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] 海洋光合成エネルギー伝達機構の解明に向けたアポカロテノイドの全合成2017

    • Author(s)
      西岡勇人、矢野陽、勝村成雄、品田哲郎、橋本秀樹、坂口和彦
    • Organizer
      第37回有機合成若手セミナー
    • Related Report
      2017 Research-status Report
  • [Presentation] 海洋光合成エネルギー伝達機構の解明に向けた多官能性アポカロテノイド、パラセントロンの全合成2017

    • Author(s)
      西岡勇人、矢野陽、勝村成雄、品田哲郎、西村貴洋、橋本秀樹、坂口和彦
    • Organizer
      第31回カロテノイド研究談話会
    • Related Report
      2017 Research-status Report

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

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