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Functional Ability Elucidation of Auxiliary Light Harvesting Carotenoids Acting in Marine Photosynthesis based on Organic Synthesis

Research Project

Project/Area Number 25410183
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

Katsumura Shigeo  大阪市立大学, 大学院理学研究科, 客員教授 (70047364)

Co-Investigator(Kenkyū-buntansha) SAKAGUCHI KAZUHIKO  大阪市立大学, 大学院理学研究科, 准教授 (80264795)
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) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords海洋光合成初期過程 / カルボニルカロテノイド / ペリジニン / フコキサンチン / デオキシペリジニン類縁体合成 / 構造的特徴と機能の関係 / 超効率的エネルギー伝達機構解明 / 海洋光合成 / ICT (分子内電荷移動) 準位 / デオキシペリジニン / Pd触媒による3種のカップリング / 立体化学を制御した合成 / 超分子 (PCP) 複合体再構成の試み / 光合成初期過程 / イリデンブテノリド / ICT準位 / 超分子複合体再構成 / 超効率的エネルギー伝達機構 / カロテノイド・ペリジニン / カロテノイド・フコキサンチン / アレン結合 / 3成分連結ワンポットカップリング / アルキニルビニルスズエステル
Outline of Final Research Achievements

Peridinin and fucoxanthin are auxiliary light harvesting pigments in the sea. In the super complexes constructed with these carotenoids, chlorophyll and apoprotain, high (>85%) energy transfer efficiencies from them to chlorophyll were reported. Previously, we substantiated the existence of intramolecular charge transfer state (ICT) by ultrafast time resolved spectra measurements (UTRSM) of the synthesized π-conjugation modified analogues. In this project, we have elucidated that ylidenbutenolide of peridinin is essential for ICT generation and allene of fucoxanthin contributes ICT stabilization, by UTRSM of β-caroten ylidenbutenolide derivatives and also C32 fucoxanthin olefin-derivatives. Intending to reconstitute the corresponding super complex, we have synthesized peridinin decarbonyl analogue by the sequential sp and sp2 couplings from E-β-ethynyl-α-stannyl acrylate, obtained by novel anti-selective ethynylstannylation of propiolate. Reconstitution has not been successful yet.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (41 results)

All 2016 2015 2014 2013 Other

All Journal Article (13 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 12 results,  Open Access: 2 results,  Acknowledgement Compliant: 1 results) Presentation (28 results) (of which Int'l Joint Research: 4 results,  Invited: 5 results)

  • [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
      2015 Annual Research Report
    • Peer Reviewed / Open Access
  • [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
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [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 / Acknowledgement Compliant
  • [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
  • [Journal Article] Total Syntheses of Zwitterionic Indole Alkaloids, Flavocarpine and Dihydrovincarpine, by Extended Method for Substituted Pyridine Synthesis through Azaelectrocyclization.2014

    • Author(s)
      Hirose, K; Kobayashi, T.; Tsuchikawa, H.; Katsumura, S.
    • Journal Title

      Heterocycles

      Volume: 90 Pages: 150-156

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Straightforward synthesis of fucoxanthin short-chain derivatives via modified-Julia olefination.2014

    • 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
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Excited state properties of a short π-electron conjugated peridinin analogue.2014

    • 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
      2013 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 Length.2014

    • 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
      2013 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 spectroscopy.2014

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

      Chem. Phys. Lett.

      Volume: 594

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Excited States Energies and Dynamics of Peridinin Analogues and the Nature of the Intramolecular Charge Transfer (ICT) State in Carbonyl-Containing Carotenoids.2013

    • Author(s)
      Dariusz, N.; Kajikawa, T.; Aoki, K.; Katsumura, S.; Frank, H.
    • Journal Title

      J. Phys. Chem. B

      Volume: 117 Pages: 6874-6887

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [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 Annual Research 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 Annual Research 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 Annual Research 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
    • Year and Date
      2016-03-17
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [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
      2015-12-15
    • Related Report
      2015 Annual Research 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
    • Year and Date
      2015-11-12
    • Related Report
      2015 Annual Research 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
    • Year and Date
      2015-11-09
    • Related Report
      2015 Annual Research 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 Annual Research 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 Annual Research 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 Annual Research 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(千葉県船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • 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(大阪府大阪市)
    • 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 18th Osaka City University International Conference
    • Place of Presentation
      Osaka City University, Media Center(大阪府大阪市)
    • 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(大阪府大阪市)
    • 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(和歌山県和歌山市)
    • 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(石川県金沢市)
    • 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(大阪府豊中市)
    • 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(沖縄県那覇市)
    • 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(Utah, USA)
    • Year and Date
      2014-06-29 – 2014-07-04
    • Related Report
      2014 Research-status Report
  • [Presentation] ペリジニン、フコキサンチン類縁体合成と光合成を担うエネルギー準位の性質2014

    • Author(s)
      梶川敬之・矢野恒記・小澄大輔・橋本秀樹・H. A. Frank・坂口和彦・木梨尚人・品田哲郎・勝村成雄
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学・東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] ペリジニンおよびフコキサンチン類縁体の合成と光合成を担うエネルギー準位の性質2013

    • Author(s)
      矢野恒記・梶川敬之・奥村聡・小澄大輔・橋本秀樹・H. A. Frank・坂口和彦・品田哲郎・勝村成雄
    • Organizer
      第57回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      埼玉大学
    • Related Report
      2013 Research-status Report
  • [Presentation] One-pot Asymmetric Azaelectrocyclization as Strategy for Alkaloid Synthesis: Total synthesis of Protoemetine2013

    • Author(s)
      Okuno, Y.; Takeuchi, Y.; Kobayashi, S.; Sakaguchi, T.; Tsuchikawa, H.; Katsumura, S.
    • Organizer
      The Eighth International Symposium on Integrated Synthesis (ISIS-8)
    • Place of Presentation
      Todaiji Temple Cultural Center, Nara, Japan
    • Related Report
      2013 Research-status Report
  • [Presentation] Polyfunctional Carotenoid Synthesis via One-pot Strategy: Toward Elucidation of Energy Transfer Process in Marine Photosynthesis2013

    • Author(s)
      Kajikawa, T.; Yano, K.; Hananoki, S.; Hasegawa, S.; Sakaguchi, K.; Shinada, T.; Katsumura, S.
    • Organizer
      The Eighth International Symposium on Integrated Synthesis (ISIS-8)
    • Place of Presentation
      Todaiji Temple Cultural Center, Nara, Japan
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of Sphingolipid Derivatives as Effective Tool Molecules

    • Author(s)
      勝村成雄
    • Organizer
      タンパク質情報交換会
    • Place of Presentation
      大阪大学理学部
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 天然物合成の魔力に40年

    • Author(s)
      勝村成雄
    • Organizer
      理研シンポジウム
    • Place of Presentation
      大阪大学会館講堂
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 機能性天然物合成とカップリング反応

    • Author(s)
      勝村成雄
    • Organizer
      近畿化学協会有機金属部会 平成25年度第2回例会
    • Place of Presentation
      早稲田大学西早稲田キャンパス
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 天然物合成の魔力に40年

    • Author(s)
      勝村成雄
    • Organizer
      関西創農薬研究会
    • Place of Presentation
      住友化学宝塚 健康・農薬研究所
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 天然物合成の魔力に40年:機能解明に向けた有機合成からのアプローチ

    • Author(s)
      勝村成雄
    • Organizer
      平成25年度 徳島文理大学薬学部学術講演会
    • Place of Presentation
      徳島文理大学
    • Related Report
      2013 Research-status Report
    • Invited

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

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