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2008 Fiscal Year Final Research Report

Studies on Supramolecular Photochirogenesis Mediated by Biopolymers

Research Project

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Project/Area Number 18350064
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Polymer chemistry
Research InstitutionTohoku University (2007-2008)
Osaka University (2006)

Principal Investigator

WADA Takehiko  Tohoku University, 多元物質科学研究所, 教授 (20220957)

Co-Investigator(Kenkyū-buntansha) MORI Tadashi  大阪大学, 大学院・工学研究科, 准教授 (70311769)
Project Period (FY) 2006 – 2008
Keywords生体高分子 / ヒト血清アルブミン / 光反応 / 超分子不斉光化学反応 / 不斉反応場 / 不斉合成
Research Abstract

本研究、自然共生型プロセスである光による不斉合成に、血清アルブミンを不斉反応場として活用する生体系高分子を用いる超分子不斉光反応という新たな方法論を提案し、この方法論の有用性を実証した。本研究で構築した生体高分子を反応場とする基底状態相互作用解析法、そして基底状態ならびに励起状態双方における相互作用制御に基づく高効率超分子不斉光化学反応の実現は、一般性を有し、今後適用反応例の拡大、基質特異性の向上により不斉光化学反応の有効な方法論としての展開が期待される。

  • Research Products

    (51 results)

All 2008 2007 2006

All Journal Article (30 results) (of which Peer Reviewed: 30 results) Presentation (21 results)

  • [Journal Article] Entrainer Effect on Photochirogenesis in Near-and Supercritical Carbon Dioxide : Dramatic Enhancement of Enantioselectivity2008

    • Author(s)
      Nishiyama, Yasuhiro ; Wada, Takehiko ; Asaoka, Sadayuki ; Mori, Tadashi ; McCarty, Taylor A.; Kraut, Nadine D.; Bright, Frank V.; Inoue, Yoshihisa
    • Journal Title

      J.Am.Chem.Soc. 130

      Pages: 7526-7527

    • Peer Reviewed
  • [Journal Article] Enantiodifferentiating Photoisomerization of Cyclooctene Included and Sensitized by Aroyl-□-cyclodextrins : A Critical Enantioselectivity Control by Substituents2008

    • Author(s)
      Lu, Runhua ; Yang, Cheng ; Cao, Yujuan ; Tong, Linhui ; Jiao, Wei ; Wada, Takehiko ; Wang, Zhizhong ; Mori, Tadashi ; Inoue, Yoshihisa
    • Journal Title

      J.Org.Chem. 73

      Pages: 7695-7701

    • Peer Reviewed
  • [Journal Article] Structural and Photophysical Properties of Self-Assembled Porphyrin Nanoassemblies Organized by Ethylene Glycol Derivatives2008

    • Author(s)
      Sandanayaka, Atula S. D.; Araki, Yasuyuki ; Wada, Takehiko ; Hasobe, Taku
    • Journal Title

      J.Phys.Chem.C 112

      Pages: 19209-19216

    • Peer Reviewed
  • [Journal Article] Supramolecular enantiodifferentiating photoisomerization of(Z)-cyclooctene in lyotropic and thermotropic liquid crystals2008

    • Author(s)
      Xiao, Debao ; Wada, Takehiko ; Inoue, Yoshihisa
    • Journal Title

      Chirality 21

      Pages: 110-113

    • Peer Reviewed
  • [Journal Article] Supramolecular complexation and photochirogenesis with inherently chiral molecular clip : enantiodifferentiating photoisomerization of(Z,Z)-1,3-cyclooctadiene and polar photoaddition to 1,1-diphenylpropene2008

    • Author(s)
      Fukuhara, Gaku ; Klaerner, Frank-Gerrit ; Mori, Tadashi ; Wada, Takehiko ; Inoue, Yoshihisa
    • Journal Title

      Photochem. Photobio. Sci. 7

      Pages: 1493-1500

    • Peer Reviewed
  • [Journal Article] Fullerene-encapsulated porphyrin hexagonal nanorods. An anisotropic donor-acceptor composite for efficient photoinduced electron transfer and light energy conversion2008

    • Author(s)
      Hasobe, Taku ; Sandanayaka, Atula S. D.; Wada, Takehiko ; Araki, Yasuyuki
    • Journal Title

      Chem.Comm.

      Pages: 3372-3374

    • Peer Reviewed
  • [Journal Article] Fluorescence resonance energy transfer between cationic porphyrins accelerated with DNA as a template2008

    • Author(s)
      D'Souza, Francis ; Rogers, Lisa M.; Islam, D.-M. Shafiqul; Araki, Yasuyuki ; Ito, Osamu ; Wada, Takehiko
    • Journal Title

      Chem. Lett. 37

      Pages: 460-461

    • Peer Reviewed
  • [Journal Article] Ethylene receptor antagonists : strained alkenes are necessary but not sufficient2008

    • Author(s)
      Pirrung, Michael C.; Bleecker, Anthony B.; Inoue, Yoshihisa ; Rodriguez, Fernando I.; Sugawara, Norimitsu ; Wada, Takehiko ; Zou, Yunfan ; Binder, Brad M
    • Journal Title

      Chem. Biology 15

      Pages: 313-321

    • Peer Reviewed
  • [Journal Article] Chiroptical properties and racemization behavior of highly distorted donor-acceptor tetracyanoanthraquinodimethane with interconvertible planar chirality2008

    • Author(s)
      Saito, Hideaki ; Mori, Tadashi ; Origane Yumi ; Wada Takehiko ; Inoue, Yoshihisa
    • Journal Title

      Chirality 20

      Pages: 278-281

    • Peer Reviewed
  • [Journal Article] Supramolecular enantiodifferentiating photoisomerization of cyclooctene with modified β-cyclodextrins : critical control by a host structure2008

    • Author(s)
      Lu, Runhua ; Yang, Cheng ; Cao, Yujuan ; Wang, Zhizhong ; Wada, Takehiko ; Jiao, Wei ; Mori, Tadashi ; Inoue, Yoshihisa
    • Journal Title

      Chem. Comm.

      Pages: 374-376

    • Peer Reviewed
  • [Journal Article] Highly Enantiomeric Supramolecular[4+4]Photocyclodimerization of 2-Anthracenecarboxylate Mediated by Human Serum Albumin2007

    • Author(s)
      Nishijima, Masaki ; Wada, Takehiko ; Mori, Tadashi ; Pace, Tamara C. S.; Bohne, Cornelia ; Inoue, Yoshihisa
    • Journal Title

      J Am. Chem. Soc. 129

      Pages: 3478-3479

    • Peer Reviewed
  • [Journal Article] Supramolecular Photochirogenesis with Biomolecules. Mechanistic Studies on the Enantiodifferentiation for the Photocyclodimerization of 2-Anthracenecarboxylate Mediated by Bovine Serum Albumin2007

    • Author(s)
      Nishijima, Masaki ; Pace, Tamara C. S.; Nakamura, Asao ; Mori, Tadashi ; Wada, Takehiko ; Bohne, Cornelia ; Inoue, Yoshihisa
    • Journal Title

      J. Org. Chem,(Cover picture, The April Calendar of JOC in 2008) 72

      Pages: 2707-2715

    • Peer Reviewed
  • [Journal Article] Mechanistic Study on the Enantiodifferentiating Anti-Markovnikov Photoaddition of Alcohols to 1,1-Diphenyl-1-alkenes in Near-Critical and Supercritical Carbon Dioxide2007

    • Author(s)
      Nishiyama, Yasuhiro ; Kaneda, Masayuki ; Asaoka, Sadayuki ; Saito, Ryota ; Mori, Tadashi ; Wada, Takehiko ; Inoue, Yoshihisa
    • Journal Title

      J.Phys.Chem.A 111

      Pages: 13432-13440

    • Peer Reviewed
  • [Journal Article] Dynamic Switching between Single-and Double-Axial Rotaxanes Manipulated by Charge and Bulkiness of Axle Termini2007

    • Author(s)
      Yang, Cheng ; Ko, Young Ho ; Selvapalam, Narayanan ; Origane, Yumi ; Mori, Tadashi ; Wada, Takehiko ; Kim, Kimoon ; Inoue, Yoshihisa
    • Journal Title

      Org.Lett. 9

      Pages: 4789-4792

    • Peer Reviewed
  • [Journal Article] Inherently chiral molecular clips : synthesis, chiroptical properties, and application to chiral discrimination2007

    • Author(s)
      Fukuhara, Gaku ; Madenci, Suereyya ; Polkowska, Jolanta ; Bastkowski, Frank ; Klaerner, Frank-Gerrit ; Origane, Yumi ; Kaneda, Masayuki ; Mori, Tadashi ; Wada, Takehiko ; Inoue, Yoshihisa
    • Journal Title

      Chem.-A Eur. J,(Cover picture) 13

      Pages: 2473-2479

    • Peer Reviewed
  • [Journal Article] Supramolecular enantiodifferentiating photoisomerization of(Z,Z)-1,3-cyclooctadiene included and sensitized by naphthalene-modified cyclodextrins2007

    • Author(s)
      Yang, Cheng ; Mori, Tadashi ; Wada, Takehiko ; Inoue, Yoshihisa
    • Journal Title

      New J.Chem. 31

      Pages: 697-702

    • Peer Reviewed
  • [Journal Article] Regioselective[2+2]-photocycloaddition reactions of chiral tetronates-influence of temperature, pressure, and reaction medium2007

    • Author(s)
      Fleck, Martin ; Yang, Cheng ; Wada, Takehiko ; Inoue, Yoshihisa ; Bach, Thorsten
    • Journal Title

      Chem.Comm.

      Pages: 822-824

    • Peer Reviewed
  • [Journal Article] A remarkable stereoselectivity switching upon solid-state versus solution-phase enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by native and 3,6-anhydro-g-cyclodextrins2007

    • Author(s)
      Yang, Cheng ; Nishijima, Masaki ; Nakamura, Asao ; Mori, Tadashi ; Wada, Takehiko ; Inoue, Yoshihisa
    • Journal Title

      Tetrahedron Lett. 48

      Pages: 4357-4360

    • Peer Reviewed
  • [Journal Article] Enhanced ternary 1:2 host-guest complexation of amino-g-cyclodextrins with 2-anthracenecarboxylic acid2007

    • Author(s)
      Yang, Cheng ; Fukuhara, Gaku ; Nakamura, Asao ; Origane, Yumi ; Mori, Tadashi ; Wada, Takehiko ; Inoue, Yoshihisa
    • Journal Title

      J. Incl. Phenom. Macrocycl. Chem. 57

      Pages: 433-437

    • Peer Reviewed
  • [Journal Article] Critical control by temperature and pressure of enantiodifferentiating anti-markovnikov photoaddition of methanol to diphenylpropene in near critical and supercritical carbon dioxide2007

    • Author(s)
      Nishiyama, Yasuhiro, Wada, Takehiko, Mori, Tadashi, Inoue, Yoshihisa
    • Journal Title

      Chem.Lett. 36

      Pages: 1488-1489

    • Peer Reviewed
  • [Journal Article] Asymmetric photosensitized addition of methanol to(R)-(+)-(Z)-limonene in a microreactor2007

    • Author(s)
      Matsushita, Yoshihisa, Ichimura, Teijiro, Suzuki, Tadashi, Wada, Takehiko, Inoue, Yoshihisa
    • Journal Title

      J.Photochem.Photobio., A : Chem. 192

      Pages: 166-171

    • Peer Reviewed
  • [Journal Article] Entropy-Controlled Supramolecular Photochirogenesis : Enantiodifferentiating Z-E Photoisomerization of Cyclooctene Included and Sensitized by Permethylated 6-O-Modified β-Cyclodextrins2006

    • Author(s)
      G. Fukuhara, T. Mori, T. Wada, and Y. Inoue
    • Journal Title

      J.Org.Chem. 71

      Pages: 8233-8233

    • Peer Reviewed
  • [Journal Article] Enantio-Differentiating Photo-Cyclodimerization of 2-Anthracene-Carboxylic Acid Mediated by γ-Cyclodextrins with a Flexible or Rigid Cap2006

    • Author(s)
      C. Yang, A. Nakamura, T. Wada, and Y. Inoue
    • Journal Title

      Org.Lett. 8

      Pages: 3005-3005

    • Peer Reviewed
  • [Journal Article] Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylic Acid Using a Chiral N-(2-Hydroxymethyl-4-pyrrolidinyl)benzamide Template2006

    • Author(s)
      J. Mizoguchi, Y. Kawanami, T. Wada, K. Kodama, K. Anzai, T. Yanagi, and Y. Inoue
    • Journal Title

      Org.Lett. 8

      Pages: 6051-6051

    • Peer Reviewed
  • [Journal Article] Solvent switching of stereoselectivity in[4+4]photocyclodimerization of 2-anthracenecarboxylic acid2006

    • Author(s)
      J. Mizoguchi, T. Wada, and Y. Inoue
    • Journal Title

      Chem.Lett. 35

      Pages: 738-738

    • Peer Reviewed
  • [Journal Article] The first supramolecular photosensitization of enantiodifferentiating bimolecular reaction: anti-Markovnikov photoaddition of methanol to 1,1-diphenylpropene sensitized by modified β-cyclodextrin2006

    • Author(s)
      G. Fukuhara, T. Mori, T. Wada, and Y. Inoue
    • Journal Title

      Chem. Comm.

      Pages: 1712-1712

    • Peer Reviewed
  • [Journal Article] Switching of Product's Chirality in Diastereodifferentiating [2+2] Photocycloaddition of (E)- versus (Z)-Stilbene to Chiral Fumarate upon Direct and Charge-Transfer-Band Excitation2006

    • Author(s)
      H. Saito, T. Mori, T. Wada, and Y. Inoue
    • Journal Title

      Org. Lett. 8

      Pages: 1909-1909

    • Peer Reviewed
  • [Journal Article] Pressure and Temperature-Controlled Enantio-Differentiating [4+4]-Photo-Cyclodimerization of 2-Anthracene-carboxylate Mediated by Secondary Face- and Skeleton-Modified γ-Cyclodextrins2006

    • Author(s)
      C. Yang, A. Nakamura, G. Fukuhara, Y. Origane, T. Mori, T. Wada, and Y. Inoue
    • Journal Title

      J. Org. Chem. 71

      Pages: 3126-3126

    • Peer Reviewed
  • [Journal Article] Absolute configuration determination of donor-acceptor [2.2]paracyclophanes by comparison of theoretical and experimental vibrational circular dichroism spectra2006

    • Author(s)
      T. Furo, T. Mori, Y. Origane, T. Wada, H. Izumi, and Y. Inoue
    • Journal Title

      Chirality 18

      Pages: 205-205

    • Peer Reviewed
  • [Journal Article] New Insights into the Geometry of Resorc[4]arenes: Solvent-Mediated Supramolecular Conformational and Chiroptical Control2006

    • Author(s)
      C. Schiel, G. A. Hembury, V. V. Borovkov, M. Klaes, C. Agena, T. Wada, S. Grimme, Y. Inoue, and J. Mattay
    • Journal Title

      J.Org.Chem. 71

      Pages: 976-976

    • Peer Reviewed
  • [Presentation] 細胞内環境応答型人工核酸の創製-がん細胞特異的遺伝治療薬開発を目指して-2008

    • Author(s)
      和田健彦
    • Organizer
      有機化学コロキウムー有機化学のフロンティアー
    • Place of Presentation
      八戸
    • Year and Date
      2008-10-11
  • [Presentation] 刺激応答性人工核酸の創製-がん細胞特異的遺伝子治療薬開発を目指して-2008

    • Author(s)
      和田健彦
    • Organizer
      第7回化学系薬学若手研究者セミナー
    • Place of Presentation
      仙台
    • Year and Date
      2008-10-04
  • [Presentation] Synthesis of Peptide Ribonucleic Acid (PRNA)-DNA Chimera and Interaction with DNA and RNA2008

    • Author(s)
      Takehiko Wada
    • Organizer
      8^th International Biorelated Polymers Symposium
    • Place of Presentation
      Philadelphia, USA
    • Year and Date
      2008-08-19
  • [Presentation] 外部刺激応答性人工核酸の創製-がん細胞特異的遺伝子治療薬の開発を目指して-2008

    • Author(s)
      和田健彦
    • Organizer
      第20回生体機能関連化学若手の会サマースクール
    • Place of Presentation
      白石
    • Year and Date
      2008-08-07
  • [Presentation] SUPRAMOLECULAR PHOTOCHIROGENESIS WITH BIOPOLYMERS, XXII^<nd> IUPAC SYMPOSIUM ON PHOTOCHEMISTRY2008

    • Author(s)
      Takehiko Wada, and Yoshihisa Inoue
    • Organizer
      Gothenburg
    • Place of Presentation
      Sweden
    • Year and Date
      2008-07-30
  • [Presentation] RNA Recognition and Complexation Behavior Control of α-Peptide Ribonucleic Acids Containing Arginine Residue by External Factors-Toward a Cancer Cell Specific Gene Therapic Compound-2008

    • Author(s)
      Takehiko Wada
    • Organizer
      35^th Controlled Release Society Annual Meeting
    • Place of Presentation
      New York, USA
    • Year and Date
      2008-07-15
  • [Presentation] アルギニン含有α-ペプチドリボ核酸とRNAとの錯体形成挙動に対するセリン導入効果2008

    • Author(s)
      和田健彦
    • Organizer
      第57回高分子年次大会
    • Place of Presentation
      横浜
    • Year and Date
      2008-05-29
  • [Presentation] Supramolecular photochirogenesis with bio-and biorelated molecules2008

    • Author(s)
      Takehiko Wada and Yoshihisa Inoue
    • Organizer
      Prof. Nicolas J. Turro's 70 Anniversary Symposium
    • Place of Presentation
      New York, USA
    • Year and Date
      2008-05-23
  • [Presentation] 生体高分子をキラル反応場とする超分子不斉光化学2008

    • Author(s)
      和田健彦
    • Organizer
      シンポジウム モレキュラー・キラリティー
    • Place of Presentation
      岡山
    • Year and Date
      2008-05-22
  • [Presentation] International Conference of 43rd Japanese Peptide Symposium2007

    • Author(s)
      Takehiko Wada
    • Organizer
      4th Peptide Engineering Meeting
    • Place of Presentation
      Yokohama, Japan
    • Year and Date
      20070000
  • [Presentation] Supramolecular Asymmetric Photochirogenesis: Enantiodifferentiating Photocyclodimerization of Anthracene Derivatives in the Presence of Bovine and Human Serum Albumins2007

    • Author(s)
      Takehiko Wada, Masaki Nishijima, Tamara C. S. Pace, Tadashi Mori, Cornelia Bohne, Yoshihisa Inoue
    • Organizer
      2007 Korea-Japan Symposium on Frontier Photoscience
    • Place of Presentation
      Gyeongju, Korea
    • Year and Date
      2007-11-25
  • [Presentation] RNA Recognition and Recognition Control of a-Peptide Ribonucleic Acids Containing Arginine Residue by External Factors2007

    • Author(s)
      Takehiko Wada, Akihiro Nishio, Nobuya Sawa, Mayuko Kikkawa, Hirofumi Sato, Shiro Futaki, Yoshihisa Inoue
    • Organizer
      4^th International Peptide Symposium
    • Place of Presentation
      Cairns, Australia
    • Year and Date
      2007-11-22
  • [Presentation] A novel strategy for reversible control of conformation and DNA/RNA recognition of peptide ribonucleic acid (PRNA) by external factors2007

    • Author(s)
      Takehiko Wada
    • Organizer
      2007 the first Japanese-Swiss Symposium on Chemical Biology(JSCB07)
    • Place of Presentation
      EPFL Lausanne, Swiss
    • Year and Date
      2007-06-26
  • [Presentation] 人工核酸を活用した新しい遺伝子治療法提案2007

    • Author(s)
      和田健彦
    • Organizer
      大阪大学大学院薬学研究科特別講演会
    • Place of Presentation
      大阪
    • Year and Date
      2007-06-12
  • [Presentation] 外部刺激応答型人工核酸の創製2007

    • Author(s)
      和田健彦
    • Organizer
      多元研講演会「核酸医薬への応用を目指した人工核酸の新しいサイエンス」
    • Place of Presentation
      仙台
    • Year and Date
      2007-05-18
  • [Presentation] 外部刺激応答性人工核酸の構築2007

    • Author(s)
      和田健彦
    • Organizer
      FIBER Lectures in NANOBIO NOW Series Part 19
    • Place of Presentation
      神戸
    • Year and Date
      2007-04-07
  • [Presentation] Enantiodifferentiating Photoisomerization of Cyclic Olefins Sensitized by Chiral [10]Paracyclophanes2007

    • Author(s)
      Takehiko Wada, Ryo Maeda, Tadashi Mori, Nobuhiro Kanomata, and Yoshihisa Inoue
    • Organizer
      ICORP Symposium 2007
    • Place of Presentation
      Osaka, Japan
    • Year and Date
      2007-01-23
  • [Presentation] 外部刺激応答型人工核酸の創製2007

    • Author(s)
      和田健彦
    • Organizer
      第19回名古屋カンファレンス
    • Place of Presentation
      名古屋
    • Year and Date
      2007-01-18
  • [Presentation] 外部刺激応答型人工核酸の創製2007

    • Author(s)
      和田健彦
    • Organizer
      第18回名古屋カンファレンス招待講演者
    • Place of Presentation
      名古屋大学・野依記念交流会館
    • Year and Date
      2007-01-18
  • [Presentation] 刺激応答型人工核酸の創製2006

    • Author(s)
      和田健彦
    • Organizer
      第52回高分子夏期大学講演者
    • Place of Presentation
      愛媛・ホテル奥道後
    • Year and Date
      2006-07-27
  • [Presentation] International Congress on Nanobiotechnology & Nanomedicine2006

    • Author(s)
      Takehiko Wada
    • Organizer
      NanoBio2006
    • Place of Presentation
      San Francisco, USA
    • Year and Date
      2006-06-20

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Published: 2010-06-10   Modified: 2016-04-21  

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