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Polyfunctional carotenoid synthesis toward elucidation of highly efficient energy transfer by marine photosynthetic organisms

Research Project

Project/Area Number 26410183
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)

Co-Investigator(Kenkyū-buntansha) 勝村 成雄  大阪市立大学, 大学院理学研究科, 客員教授 (70047364)
Co-Investigator(Renkei-kenkyūsha) HASHIMOTO HIDEKI  大阪市立大学, 複合先端研究機構, 教授 (50222211)
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsフコキサンチン / 海洋光合成初期過程 / 超分子複合体 / ICT準位 / 超効率的エネルギー伝達 / パラセントロン / 光合成初期過程 / 両官能性C5ジエン / クロスカップリング / スフェロイデノン / 両官能性C5ジエンユニット / クロスカップリング反応 / 両官能性ジエン / カロテノイド / エネルギー伝達
Outline of Final Research Achievements

The highly oxidized marine carotenoid fucoxanthin is a representative light-harvesting pigment for photosynthesis in the sea. This carotenoid exhibits exceptionally high-energy transfer efficiency (>85%) in the fucoxanthin -chlorophyll a-protein (FCP) complex. In this project, we succeeded in the synthesis of natural apocarotenoid paracentrone, which was a one cyclohexane-moiety free analogue of fucoxanthin, and its derivatives by the sequential cross coupling reactions of novel bifunctional C5 diene units as key building brocks. The ultrafast time resolved spectra measurement of paracentrone revealed that this carotenoid possessed the intramolecular charge transfer (ICT) state, which contributed to the remarkably high light-harvesting efficiency in marine photosynthesis. Toward elucidation of the mechanism of this super function by marine photosynthetic organisms, reconstitution of the corresponding super complex containing paracentrone is in progress.

Report

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

    (39 results)

All 2017 2016 2015 2014

All Journal Article (10 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 9 results,  Acknowledgement Compliant: 3 results,  Open Access: 2 results) Presentation (29 results) (of which Int'l Joint Research: 8 results)

  • [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
      2016 Annual Research 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
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [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
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Spectroscopic investigation of the carotenoid deoxyperidinin: direct observation of the forbidden S0 → S1 transition2016

    • Author(s)
      Greco, J. A., LaFountain, A. M., Kinashi, N., Shinada, T., Sakaguchi, K., Katsumura, S., S., Magdaong, S., Niedzwiedzki, D.M.R., Birge, R.H., Frank, A.
    • Journal Title

      The Journal of Physiological Chemistry B

      Volume: 120 Issue: 10 Pages: 2731-2734

    • DOI

      10.1021/acs.jpcb.6b00439

    • Related Report
      2016 Annual Research Report 2015 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Preparation of E-α-stannyl-β-trimethylsilylethynylacrylate, building block for polyconjugated ylidenebutenolide and its derivatives, by novel E-selective ethynylstannylation of propiolate2016

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

      Tetrahedron Letters

      Volume: 57 Issue: 1 Pages: 129-132

    • DOI

      10.1016/j.tetlet.2015.11.079

    • Related Report
      2016 Annual Research Report 2015 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Straightforward synthesis of fucoxanthin short-chain derivatives via modified-Julia olefination2014

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

      Tetrahedron Lett.

      Volume: 55 Pages: 407-410

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Excited state properties of a short π-electron conjugated peridinin analogue2014

    • Author(s)
      Magdaong, N. M.; Niedzwiedzki, D. M.; Greco, J. A.; Liu, H.; Yano, K.; Kajikawa, T.; Sakaguchi, K.; Katsumura, S.; Birge, R. R.; Frank, H. A.
    • Journal Title

      Chem. Phys. Lett.

      Volume: 593 Pages: 132-139

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Elucidation and Control of an Intramolecular Charge Transfer Property of Fucoxanthin by a Modification of Its Polyene Chain Length2014

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

      J. Phys. Chem. Lett.

      Volume: 5 Pages: 792-797

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Roles of allene-group in an intramolecular charge transfer character of a short fucoxanthin homologue as revealed by femtosecond pump-probe spectroscopy2014

    • Author(s)
      Kosumi, D.; Kajikawa, T.; Yano, K.; Okumura, S.; Sugisaki, M.; Sakaguchi, K.; Katsumura, S.; Hashimoto, H.
    • Journal Title

      Chem. Phys. Lett.

      Volume: 602 Pages: 75-79

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Ultrafast excited state dynamics of marine carotenoid fucoxanthin and its homologues2014

    • Author(s)
      H. Hashimoto, D. Kosumi, R. Fujii, M. Sugisaki, M. Iha, K. Sakaguchi, and S. Katsumura
    • Journal Title

      Carotenoid Science

      Volume: 118 Pages: 4-4

    • Related Report
      2014 Research-status Report
  • [Presentation] Total Synthesis of Paracentrone Using Bifunctional C5 Diene Units2017

    • Author(s)
      Y. Nishioka, Y. Yano, N. Kinashi, N. Oku, Y. Toriyama, S. Katsumura, T. Shinada, K. Sakaguchi
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス(神奈川、横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Investigation of the fucoxanthin reconstituted light-harvesting 1 complex from a purple photosynthetic bacterium rubrum G9+2017

    • Author(s)
      N. Yukihira, Y. Sugai, M. Fujiwara, D. Kosumi, M. Iha, K. Sakaguchi, S. Katsumura, A. T. Gardiner, R. J. Cogdell and H. Hashimoto
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス(神奈川、横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Reconstitution of the Light-harvesting 1 Complex from a Purple Photosynthetic Bacterium Rhodospirillum rubrum G9+ with Fucoxanthin2017

    • Author(s)
      N. Yukihira, Y. Sugai, M. Fujiwara, D. Kosumi, M. Iha, K. Sakaguchi, S. Katsumura, A. T. Gardiner, R. J. Cogdell and H. Hashimoto
    • Organizer
      2017 International Conference on Artificial Photosynthesis (ICARP 2017)
    • Place of Presentation
      Ritsumeikann University (Kyoto, Kyoto City)
    • Year and Date
      2017-03-02
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Energy-transfer efficiency of fucoxanthin reconstituted into the light-harvesting 1 complex from a purple photosynthetic bacterium Rhodospirillum rubrum G9+2016

    • Author(s)
      N. Yukihira, Y. Sugai, M. Fujiwara, C. Uragami, D. Kosumi, K. Sakaguchi, S. Katsumura, A. T. Gardiner, R. J. Cogdell, and H. Hashimoto
    • Organizer
      The 23rd International SPACC (The Society of Pure and Applied Coordination Chemistry) Symposium; Functional complexes and their new applications
    • Place of Presentation
      Okayama University of Science (Okayama, Okayama City)
    • Year and Date
      2016-11-21
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Total Synthesis of Paracentrone2016

    • Author(s)
      Y. Nishioka, Y. Yano, N. Kinashi, N. Oku, Y. Toriyama, S. Katsumura, T. Shinada, K. Sakaguchi
    • Organizer
      The 10th International Symposium on Integrated Synthesis (ISONIS-10)
    • Place of Presentation
      Awaji Yumebutai International Conference Center (Hyogo, Awaji City)
    • Year and Date
      2016-11-18
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Total Synthesis of Paracentrone2016

    • Author(s)
      Y. Nishioka, Y. Yano, N. Kinashi, N. Oku, Y. Toriyama, S. Katsumura, T. Shinada, K. Sakaguchi
    • Organizer
      International Symposium on Natural Products for the Future 2016 Tokushima
    • Place of Presentation
      Tokushima Bunri University (Tokushima, Tokushima City)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] モデルカロテノイドにおける分子内電荷移動状態の解明2016

    • Author(s)
      小澄大輔、梶川敬之、坂口和彦、勝村成雄、橋本秀樹
    • Organizer
      光合成セミナー2016:反応中心と色素系の多様性
    • Place of Presentation
      龍谷大学深草キャンパス(京都、京都市)
    • Year and Date
      2016-07-09
    • Related Report
      2016 Annual Research Report
  • [Presentation] カルボニル基を導入したβ-carotene類縁体の光学応答2016

    • Author(s)
      小澄大輔、梶川敬之、坂口和彦、勝村成雄、橋本秀樹
    • Organizer
      第30回カロテノイド研究談話会
    • Place of Presentation
      ホテルムーンビーチ(沖縄、恩納村)
    • Year and Date
      2016-06-25
    • Related Report
      2016 Annual Research Report
  • [Presentation] 紅色光合成細菌 Rs. rubrum G9+ のLH1 サブユニット型複合体とフコキサンチンを用いた LH1 複合体の再構成2016

    • Author(s)
      行平奈央、須貝祐子、藤原正澄、浦上千藍紗、小澄大輔、伊波匡彦、坂口和彦、勝村成雄、橋本秀樹
    • Organizer
      第30回カロテノイド研究談話会
    • Place of Presentation
      ホテルムーンビーチ(沖縄、恩納村)
    • Year and Date
      2016-06-25
    • Related Report
      2016 Annual Research Report
  • [Presentation] Total Synthesis of Paracentrone2016

    • Author(s)
      西岡勇人、矢野陽、木梨尚人、奥菜津未、鳥山陽平、勝村成雄、品田哲郎、坂口和彦
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府・京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 海洋性カロテノイドであるフコキサンチン類縁体(パラセントロン)のフェムト秒時間分解吸収分光2016

    • Author(s)
      橋本秀樹、行平奈央、藤原正澄、西岡勇人、品田哲郎、坂口和彦、勝村成雄
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府・京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 紅色光合成細菌 Rs. rubrum の LH1 サブユニット型複合体とフコキサンチンを用いた再構成LH1 複合体のフェムト秒時間分解吸収分光2016

    • Author(s)
      橋本秀樹、行平奈央、須貝祐子、藤原正澄、浦上千藍紗、伊波匡彦、坂口和彦、勝村成雄
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府・京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Total Synthesis of Paracentrone2016

    • Author(s)
      Y. Nishioka, Y. Yano, N. Kinashi, N. Oku, Y. Toriyama, S. Katsumura, T. Shinada, K. Sakaguchi
    • Organizer
      The 2016 OCARINA Annual International Meeting
    • Place of Presentation
      Osaka City University, Media Center, Osaka (Osaka city)
    • Year and Date
      2016-03-17
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Paracentroneの全合成2016

    • Author(s)
      西岡勇人、矢野陽、木梨尚人、奥菜津未、鳥山陽平、勝村成雄、品田哲郎、坂口和彦
    • Organizer
      第36回有機合成若手セミナー
    • Place of Presentation
      京都薬科大学(京都、京都市)
    • Related Report
      2016 Annual Research Report
  • [Presentation] Polyfunctional carotenoid synthesis via one-pot strategy: Toward elucidation of highly efficient energy transfer by marine photosynthetic organisms2015

    • Author(s)
      K. Sakaguchi, T. Kajikawa, S. Hananoki, N. Kinashi, D. Kosumi, H. Hashimoto, H. A. Frank, T. Shinada, S. Katsumura
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015)
    • Place of Presentation
      Hawaii Convention Center, Honolulu, Hawaii, USA
    • Year and Date
      2015-12-12
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Total Synthesis of Paracentrone2015

    • Author(s)
      N. Oku, Y. Nishioka, Y. Yano, N. Kinashi, S. Katsumura, T. Shinada, and K. Sakaguchi
    • Organizer
      The 19th Osaka City University International Workshop on Advanced Molecular Materials Science
    • Place of Presentation
      Osaka City University, Media Center, Osaka (Osaka city)
    • Year and Date
      2015-11-12
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Development of E-β-Ethynyl-α-stannylacrylate Toward Efficient Synthesis of Polyfunctional Carotenoids2015

    • Author(s)
      K. Sakaguchi, N. Kinashi, H. A. Frank, S. Katsumura, T. Shinada
    • Organizer
      the Twelfth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)
    • Place of Presentation
      Rihga Royal Hotel Kyoto, Kyoto (Kyoto city)
    • Year and Date
      2015-11-09
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 共役ケトンを有するアポカロテノイドの全合成研究2015

    • Author(s)
      西岡勇人、矢野陽、木梨尚人、奥菜津未、鳥山陽平、勝村成雄、品田哲郎、坂口和彦
    • Organizer
      第59回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      近畿大学(大阪府・東大阪市)
    • Year and Date
      2015-09-05
    • Related Report
      2015 Research-status Report
  • [Presentation] デオキシペリジニンの合成研究2015

    • Author(s)
      坂口和彦、木梨尚人、西岡勇人、奥菜津未、鳥山陽平、H. A. Frank、勝村成雄、品田哲郎
    • Organizer
      第59回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      近畿大学(大阪府・東大阪市)
    • Year and Date
      2015-09-05
    • Related Report
      2015 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新規多官能性カロテノイドの設計と合成2015

    • Author(s)
      坂口和彦、木梨尚人、西岡勇人、奥菜津未、鳥山陽平、H. A. Frank、勝村成雄、品田哲郎
    • Organizer
      第29回カロテノイド研究談話会
    • Place of Presentation
      首都大学東京(東京都。八王子市)
    • Year and Date
      2015-09-04
    • Related Report
      2015 Research-status Report
  • [Presentation] Development of Novel E-β-Ethynylvinylstannane for Cross Coupling Reaction and Efficient Synthesis of Peridinin Derivatives2015

    • Author(s)
      木梨尚人・坂口和彦・品田哲郎・勝村成雄
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学・船橋キャンパス(千葉)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Direct Preparation of E-beta-Ethynyl-alpha-stannylacrylate as Effective Building Block for Peridinin Synthesis by Novel E-Selective Ethynylstannylation of Propiolate2015

    • Author(s)
      N. Kinashi, K. Sakaguchi, T. Shinada and S. Katsumura
    • Organizer
      The 18th Osaka City University International Conference
    • Place of Presentation
      Osaka City University, Media Center(大阪)
    • Year and Date
      2015-03-09
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthetic Study of Paracentrone using Cross Coupling Method2015

    • Author(s)
      Y. Nishioka, N. Kinashi, K. Sakaguchi, T. Shinada and S. Katsumura
    • Organizer
      The 18th Osaka City University International Conference
    • Place of Presentation
      Osaka City University, Media Center(大阪)
    • Year and Date
      2015-03-09
    • Related Report
      2014 Research-status Report
  • [Presentation] Direct Preparation of E-beta-Ethynyl-alpha-stannylacrylate as Effective Building Block for Peridinin Synthesis by Novel E-Selective Ethynylstannylation of Propiolate2015

    • Author(s)
      N. Kinashi, K. Sakaguchi, T. Shinada and S. Katsumura
    • Organizer
      The 2014 OCARINA Annual International Meeting
    • Place of Presentation
      Osaka City University, Media Center(大阪)
    • Year and Date
      2015-03-04 – 2015-03-05
    • Related Report
      2014 Research-status Report
  • [Presentation] クロスカップリングに有用な新規アルキニルスズの開発とペリジニン類の効率的合成研究2014

    • Author(s)
      木梨尚人・坂口和彦・小澄大輔・橋本秀樹・品田哲郎・勝村成雄
    • Organizer
      第58回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      和歌山大学(和歌山)
    • Year and Date
      2014-09-20 – 2014-09-22
    • Related Report
      2014 Research-status Report
  • [Presentation] イリデンブテノリドを骨格に含むカロテノイド類の合成と励起エネルギー準位特性2014

    • Author(s)
      坂口和彦・梶川敬之・矢野恒記・長谷川愼二・花ノ木祥平・小澄大輔・橋本秀樹・H. A. Frank・木梨尚人・品田哲郎・勝村成雄
    • Organizer
      第28回カロテノイド研究談話会
    • Place of Presentation
      石川県文教会館(石川)
    • Year and Date
      2014-09-04 – 2014-09-05
    • Related Report
      2014 Research-status Report
  • [Presentation] 新規アンチ挿入型エチニルスタニル化反応の開発とペリジニン骨格ワンポット合成への展開2014

    • Author(s)
      木梨尚人・坂口和彦・品田哲郎・勝村成雄
    • Organizer
      第34回有機合成若手セミナー
    • Place of Presentation
      大阪大学豊中キャンパス(大阪)
    • Year and Date
      2014-08-05
    • Related Report
      2014 Research-status Report
  • [Presentation] Elucidation and Control of Ultrafast Intramolecular Charge Transfer Dynamics of Marine Photosynthetic Pigments2014

    • Author(s)
      D. Kosumi, T. Kajikawa, K. Yano, S. Okumura, M. Sugisaki, K. Sakaguchi, S. Katsumura, H. Hashimoto
    • Organizer
      19th International Conference on Ultrafast Phenomena
    • Place of Presentation
      Okinawa Convention Center, Naha(沖縄)
    • Year and Date
      2014-07-07 – 2014-07-11
    • Related Report
      2014 Research-status Report
  • [Presentation] Ultrafast excited state dynamics of marine carotenoid fucoxanthin and its homologues2014

    • Author(s)
      Hideki Hashimoto, Daisuke Kosumi, Ritsuko Fujii, Mitsuru Sugisaki, Masahiko Iha, Kazuhiko Sakaguchi, and Shigeo Katsumura
    • Organizer
      17th International Symposium on Carotenoids
    • Place of Presentation
      Park City, Utah(USA)
    • Year and Date
      2014-06-29 – 2014-07-04
    • Related Report
      2014 Research-status Report

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

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