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2014 Fiscal Year Annual Research Report

光合成系をモデルとした光応答超分子ナノデバイスの構築

Research Project

Project/Area Number 22245030
Research InstitutionRitsumeikan University

Principal Investigator

民秋 均  立命館大学, 薬学部, 教授 (00192641)

Project Period (FY) 2010-04-01 – 2015-03-31
Keywords超分子化学 / 光物性 / マイクロ・ナノデバイス / 生体分子 / 光合成
Outline of Annual Research Achievements

1. 会合性ポルフィリン類の合成:緑色光合成細菌の主たる光合成アンテナであるクロロゾームにおけるクロロフィル分子をモデルとして、アキシャル配位子を取りやすいクロロフィル誘導体の亜鉛錯体を新たに合成した。3位上の置換基として従来の酸素官能基以外に窒素や硫黄官能基の導入や、13位のケトカルボニル基の(ジ)シアノエチレン基への改変に成功した。またクロスカップリング法を利用して20位に様々な炭化水素基を導入することにも成功した。さらに、緑色光合成細菌のクロロフィル合成酵素の一つである8-ビニル還元酵素を欠損させた変異株を利用して、8位にビニル基有するクロロゾーム型クロロフィルを新たに調製した。
2. J会合体の構築:上述の半合成あるいは生合成ポルフィリン分子を、ヘキサンのような疎水性有機溶媒中や中性界面活性剤であるTriton X-100水溶液中に分散させて、クロロゾーム型J会合体を形成させることに成功した。31位の水酸基以外に、一級アミノ基でもがあってもJ会合体を形成しうるが、チオール基では二量体のような小さい会合体しか形成しなかった。また、13位への電子吸引基の導入と、20位への立体的に比較的込み合っていない置換基の導入が、J会合体形成にとって有用であることも判明した。
3. 超分子系の機能解明:バクテリオクロロフィルeを構成分子とする緑色硫黄細菌のクロロゾームにおける光収穫・励起エネルギー移動を、低温・高速2次元電子相関分光法を用いて検討し、その自己会合体内で超高速・高効率での励起子移動を確認した。
4. 光応答超分子ナノデバイスの創製:2で示したJ会合体をガラス基板上で調製することに成功し、さらにその上に光励起エネルギー受容体となる新たな分子を修飾することにも成功した。このような2成分系では、励起一重項エネルギー移動が可能であり、人工光合成アンテナとして機能した。

Research Progress Status

26年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

26年度が最終年度であるため、記入しない。

  • Research Products

    (40 results)

All 2015 2014 Other

All Journal Article (23 results) (of which Peer Reviewed: 23 results,  Acknowledgement Compliant: 20 results) Presentation (14 results) (of which Invited: 13 results) Book (2 results) Remarks (1 results)

  • [Journal Article] Synthesis of methyl C132-alkylated pheophorbides a/a' and their stereochemical characterization2015

    • Author(s)
      S. Ogasawara, H. Tamiaki
    • Journal Title

      Tetrahedron: Asymmetry

      Volume: 26 Pages: 46-52

    • DOI

      10.1016/j.tetasy.2014.11.017

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] The 17-propionate esterifying variants of bacteriochlorophyll-a and bacteriopheophytin-a in purple photosynthetic bacteria2015

    • Author(s)
      T. Mizoguchi, M. Isaji, J. Harada, Y. Tsukatani, H. Tamiaki
    • Journal Title

      J. Photochem. Photobiol. B: Biol.

      Volume: 142 Pages: 244-249

    • DOI

      10.1016/j.jphotobiol.2014.12.013

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and physical properties of carbonylated chlorophyll derivatives2015

    • Author(s)
      H. Tamiaki, T. Tanaka
    • Journal Title

      Tetrahedron

      Volume: 71 Pages: 1915-1923

    • DOI

      10.1016/j.tet.2015.02.026

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of carboxylated chlorophylls and their application as functional materials2015

    • Author(s)
      S. Sasaki, X.-F. Wang, T. Ikeuchi, H. Tamiaki
    • Journal Title

      J. Porphyrins Phthalocyanines,

      Volume: 19 Pages: 517-526

    • DOI

      10.1142/S1088424615500418

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis, optical properties and protonation of chlorophyll derivatives appending a pyridyl group in the C3-substituent2015

    • Author(s)
      Y. Yamamoto, H. Tamiaki
    • Journal Title

      Dyes Pigments

      Volume: 118 Pages: 159-165

    • DOI

      10.1016/j.dyepig.2015.03.006

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rhodobacter sphaeroides mutants overexpressing chlorophyllide a oxidoreductase of Blastochloris viridis elucidate functions of enzymes in late bacteriochlorophyll biosynthetic pathways2015

    • Author(s)
      Y. Tsukatani, J. Harada, J. Nomata, H. Yamamoto, Y. Fujita, T. Mizoguchi, H. Tamiaki
    • Journal Title

      Sci. Rep.

      Volume: 5 Pages: 9741-1-8

    • DOI

      10.1038/srep09741

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Photophysical properties of synthetic monomer, dimer, trimer, and tetramer of chlorophyll derivatives and their application to organic solar cells2015

    • Author(s)
      H. Tamiaki, T. Tanaka, X.-F. Wang
    • Journal Title

      J. Photochem. Photobiol. A: Chem.

      Volume: 未定 Pages: 印刷中

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Isolation and characterization of a new bacteriochlorophyll-c bearing a neopentyl substituent at the C8-position from the bciD-deletion mutant of the brown-colored green sulfur bacterium Chlorobaculum limnaeum2014

    • Author(s)
      T. Mizoguchi, J. Harada, Y. Tsukatani, H. Tamiaki
    • Journal Title

      Photosynth. Res.

      Volume: 121 Pages: 3-12

    • DOI

      10.1007/s11120-014-9977-8

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of amino-analogs of bacteriochlorophyll-d and their self-aggregation in an aqueous micelle solution2014

    • Author(s)
      H. Tamiaki, T. Nagai, K. Mizutani, S. Machida
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 24 Pages: 1668-1671

    • DOI

      10.1016/j.bmcl.2014.02.062

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Self-aggregation of a synthetic zinc chlorophyll derivative possessing a 131-dicyanomethylene group as a light-harvesting antenna model2014

    • Author(s)
      H. Tamiaki, M. Kuno, M. Kunieda
    • Journal Title

      Tetrahedron Lett.

      Volume: 55 Pages: 2825-2828

    • DOI

      10.1016/j.tetlet.2014.03.071

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Chlorophyllide a oxidoreductase works as one of divinyl reductase specifically in bacteriochlorophyll a biosynthesis2014

    • Author(s)
      J. Harada, T. Mizoguchi, Y. Tsukatani, M. Yokono, A. Tanaka, H. Tamiaki
    • Journal Title

      J. Biol. Chem.

      Volume: 289 Pages: 12716-12726

    • DOI

      10.1074/jbc.M113.546739

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Isolation and structural determination of C8-vinyl-bacteriochlorophyll d from the bciA and bchU double mutant of the green sulfur bacterium Chlorobaculum tepidum2014

    • Author(s)
      J. Harada, T. Mizoguchi, K. Nomura, H. Tamiaki
    • Journal Title

      Photosynth. Res.

      Volume: 121 Pages: 13-23

    • DOI

      10.1007/s11120-014-0007-7

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Coherent oscillations in chlorosome elucidated by two-dimensional electronic spectroscopy2014

    • Author(s)
      S. Jun, C. Yang, M. Isaji, H. Tamiaki, J. Kim, H. Ihee
    • Journal Title

      J. Phys. Chem. Lett.

      Volume: 5 Pages: 1386-1392

    • DOI

      10.1021/jz500328w

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Regioselective addition of amines to the trifluoromethyl-b-diketonate moiety of a chlorophyll derivative2014

    • Author(s)
      Y. Kinoshita, H. Tamiaki
    • Journal Title

      J. Porphyrins Phthalocyanines

      Volume: 18 Pages: 471-474

    • DOI

      10.1142/S1088424614500217

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of zinc 20-substituted bacteriochlorophyll-d analogs and their self-aggregation2014

    • Author(s)
      H. Tamiaki, S. Matsunaga, Y. Taira, A. Wada, Y. Kinoshita, M. Kunieda
    • Journal Title

      Tetrahedron Lett.

      Volume: 55 Pages: 3351-3354

    • DOI

      10.1016/j.tetlet.2014.04.057

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] C132-Methylation of methyl pheophorbide a and stereoselective preparation of methyl (132R)-methylpyropheophorbide a2014

    • Author(s)
      S. Ogasawara, H. Tamiaki
    • Journal Title

      Tetrahedron Lett.

      Volume: 55 Pages: 3618-3621

    • DOI

      10.1016/j.tetlet.2014.04.123

    • Peer Reviewed
  • [Journal Article] Synthesis and photophysical properties of phenyl-sulfanylated chlorophyll derivatives2014

    • Author(s)
      N. Takei, M. Morioka, M. Yoshizato, T. Tanaka, S. Sasaki, S. Itoh, H. Tamiaki, T. Oba
    • Journal Title

      Tetrahedron

      Volume: 70 Pages: 5109-5113

    • DOI

      10.1016/j.tet.2014.05.115

    • Peer Reviewed
  • [Journal Article] Synthesis of chlorophyll-f analogs possessing the 2-formyl group by modifying chlorophyll-a2014

    • Author(s)
      M. Xu, Y. Kinoshita, H. Tamiaki
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 24 Pages: 3997-4000

    • DOI

      10.1016/j.bmcl.2014.06.022

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Dark-operative protochlorophyllide oxidoreductase generates substrate radicals by an iron-sulphur enzyme in bacteriochlorophyll biosynthesis2014

    • Author(s)
      J. Nomata, T. Kondo, T. Mizoguchi, H. Tamiaki, S. Itoh, Y. Fujita
    • Journal Title

      Sci. Rep.

      Volume: 4 Pages: 5455-1-7

    • DOI

      10.1038/srep05455

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Self-aggregation of synthetic zinc chlorophyll derivatives possessing 31-hydroxy or methoxy group and 131-mono- or dicyanomethylene moiety in non-polar organic solvents as models of chlorosomal bacteriochlorophyll-d aggregate2014

    • Author(s)
      H. Tamiaki, M. Kuno, M. Ohata
    • Journal Title

      Photochem. Photobiol.

      Volume: 90 Pages: 1277-1286

    • DOI

      10.1111/php.12327

    • Peer Reviewed
  • [Journal Article] Asymmetry of chlorophylls in photosynthetic proteins: from the viewpoint of coordination chemistry2014

    • Author(s)
      T. Oba, H. Tamiaki
    • Journal Title

      J. Porphyrins Phthalocyanines

      Volume: 18 Pages: 919-932

    • DOI

      10.1142/S1088424614500710

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Transformation of natural chlorophyll-a into chlorophyll-c analogs possessing the 17-acrylate residu2014

    • Author(s)
      M. Xu, H. Tamiaki
    • Journal Title

      Chem. Lett.

      Volume: 43 Pages: 1864-1866

    • DOI

      10.1246/cl.140798

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 20-iodochlorophyll derivatives and their properties including reactivity, electronic absorption, and self-aggregation2014

    • Author(s)
      H. Tamiaki, N. Ariki, T. Yasuda, T. Miyatake, T. Oba
    • Journal Title

      Tetrahedron

      Volume: 70 Pages: 9768-9775

    • DOI

      10.1016/j.tet.2014.11.032

    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Artificial photosynthetic antennas using synthetic chlorophylls2015

    • Author(s)
      H. Tamiaki
    • Organizer
      NUS-Rits Bilateral Symposium on Functional p-Conjugated Molecules
    • Place of Presentation
      シンガポール(シンガポール)
    • Year and Date
      2015-01-26
    • Invited
  • [Presentation] Artificial light-harvesting antenna systems using semi-synthetic chlorophyll derivative2014

    • Author(s)
      H. Tamiaki
    • Organizer
      1回人工光合成国際会議(ICARP2014)
    • Place of Presentation
      明石夢舞台国際会議場(兵庫県)
    • Year and Date
      2014-11-26
    • Invited
  • [Presentation] クロロフィルの分子構造と光機能2014

    • Author(s)
      民秋 均
    • Organizer
      第26回配位化合物の光化学討論会
    • Place of Presentation
      首都大学東京(東京都)
    • Year and Date
      2014-08-07
    • Invited
  • [Presentation] クロロフィルfのモデル合成とその光物性2014

    • Author(s)
      民秋 均、徐 美芸、木下雄介
    • Organizer
      第22回光合成セミナ-
    • Place of Presentation
      名古屋工業大学(愛知県)
    • Year and Date
      2014-07-13
  • [Presentation] Self-aggregation of semi-synthetic chlorophyll derivatives and their supramolecular structures2014

    • Author(s)
      H. Tamiaki, T. Miyanaga, S. Shoji
    • Organizer
      ICPP-8
    • Place of Presentation
      イスタンブール(トルコ)
    • Year and Date
      2014-06-26
    • Invited
  • [Presentation] Chlorophyllide a oxidoreductase catalyzes the formation of an ethylidene group of bacteriochlorophyll b2014

    • Author(s)
      Y. Tsukatani, H. Yamamoto, J. Harada, J. Nomata, T. Mizoguchi, Y. Fujita, H. Tamiaki
    • Organizer
      ICPP-8
    • Place of Presentation
      イスタンブール(トルコ)
    • Year and Date
      2014-06-23
    • Invited
  • [Presentation] 132,173-Cyclopheophorbide enols as detoxified catabolites of chlorophylls - a widely distributed metabolism among phototrophic/heterotrophic protists2014

    • Author(s)
      Y. Kashiyama, A. Yokoyama, H. Tamiaki
    • Organizer
      ICPP-8
    • Place of Presentation
      イスタンブール(トルコ)
    • Year and Date
      2014-06-23
    • Invited
  • [Presentation] クロロフィルの構造と機能に関する研究2014

    • Author(s)
      民秋 均
    • Organizer
      大阪大学基礎工学部講演会
    • Place of Presentation
      大阪大学(大阪府)
    • Year and Date
      2014-06-13
    • Invited
  • [Presentation] クロロフィルを制したものが光環境を征した―プロティストと二次植物の進化2014

    • Author(s)
      柏山祐一郎、民秋 均
    • Organizer
      第5回光合成学会年会
    • Place of Presentation
      近畿大学(奈良県)
    • Year and Date
      2014-05-31
    • Invited
  • [Presentation] Photochemical Reduction of CO2 with Long-Wavelength Light by Covalently Linked Chlorophyll-Rhenium Bipyridine Complexes2014

    • Author(s)
      Y. Kitagawa, H. Tamiaki
    • Organizer
      SNCPP14
    • Place of Presentation
      立命館大学(滋賀県)
    • Year and Date
      2014-05-31
    • Invited
  • [Presentation] Excitation Energy Transfer and Coherent Oscillations in Chlorosome Elucidated by Two-Dimensional Electronic Spectroscopy2014

    • Author(s)
      S. Jun, C. Yang, M. Isaji, H. Tamiaki, H. Ihee, J. Kim
    • Organizer
      SNCPP14
    • Place of Presentation
      立命館大学(滋賀県)
    • Year and Date
      2014-05-31
    • Invited
  • [Presentation] Application of Photosynthetic Pigments in Organic Photovoltaic Cells2014

    • Author(s)
      X.-F. Wang, S. Sasaki, H. Tamiaki
    • Organizer
      SNCPP14
    • Place of Presentation
      立命館大学(滋賀県)
    • Year and Date
      2014-05-31
    • Invited
  • [Presentation] クロロフィルの構造と機能に関する研究2014

    • Author(s)
      民秋 均
    • Organizer
      JSTさきがけ「光エネルギーと物質変換」研究領域第9回領域会議
    • Place of Presentation
      八ヶ岳ロイヤルホテル(山梨県)
    • Year and Date
      2014-05-24
    • Invited
  • [Presentation] クロロフィルを利用した光エネルギー変換系の創製2014

    • Author(s)
      民秋 均
    • Organizer
      2014年度第1回太陽光発電によるエネルギー創成・利用研究拠点・研究会
    • Place of Presentation
      立命館大学(滋賀県)
    • Year and Date
      2014-04-14
    • Invited
  • [Book] 光化学の事典2014

    • Author(s)
      民秋 均
    • Total Pages
      2
    • Publisher
      朝倉書店
  • [Book] 光合成研究と産業応用最前線2014

    • Author(s)
      溝口 正、民秋 均
    • Total Pages
      10
    • Publisher
      エヌ・ティー・エス
  • [Remarks] 立命館大学大学院生命科学研究科(薬学部薬学科) 生物有機化学研究室

    • URL

      http://www.ritsumei.ac.jp/se/rc/staff/tamiaki/lab.html

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Published: 2016-06-01  

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