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Supramolecular Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate with Proteins and Protein-Polymer Hybrids as Chiral Reaction Medias

Research Project

Project/Area Number 24245044
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Polymer/Textile materials
Research InstitutionTohoku University

Principal Investigator

WADA Takehiko  東北大学, 多元物質科学研究所, 教授 (20220957)

Co-Investigator(Kenkyū-buntansha) YASUYUKI Araki  東北大学, 多元物質科学研究所, 准教授 (80361179)
SAKAMOTO Seiji  東北大学, 多元物質科学研究所, 助教 (30335228)
Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥46,020,000 (Direct Cost: ¥35,400,000、Indirect Cost: ¥10,620,000)
Fiscal Year 2014: ¥5,850,000 (Direct Cost: ¥4,500,000、Indirect Cost: ¥1,350,000)
Fiscal Year 2013: ¥20,540,000 (Direct Cost: ¥15,800,000、Indirect Cost: ¥4,740,000)
Fiscal Year 2012: ¥19,630,000 (Direct Cost: ¥15,100,000、Indirect Cost: ¥4,530,000)
Keywords生体高分子 / 血清アルブミン / キラル反応場 / 不斉合成 / 光反応 / 超分子 / 超分子不斉光反応 / PEG / 合成坑体 / 不斉光反応 / 超分子不斉光化学 / 人工坑体 / 2-アントラセンカルボン酸 / ファージディスプレイ法 / キラルソフト界面
Outline of Final Research Achievements

Increasing attention has recently been directed toward the new methodology of asymmetric photochemistry using various supramolecules as chiral reaction medias. In this project, we have discussed about the novel strategy and recent results of supramolecular asymmetric photochirogenesis (SMAP) with tailor-made biopolymers as chiral reaction medias. We have reported the enantiodifferentiating photocyclodimerization of 2-antharcenecarboxylate (AC) mediated by bovine and human serum albumin (BSA & HSA) as a chiral reaction media to give the [4+4]-cyclodimers with high enantioselectivities of up to 90 % ee. In this project, effects of polyethylene glycol (PEG) modification of BSA and HSA upon in the ground state and in the excited state interaction with AC were discussed. Additionally supramolecular photochirogenesis of AC dimerization with PEG modified BSA and HSA as chiral reaction medias were also discussed.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • Research Products

    (34 results)

All 2015 2014 2013 2012

All Journal Article (18 results) (of which Peer Reviewed: 18 results,  Acknowledgement Compliant: 1 results) Presentation (15 results) (of which Invited: 9 results) Book (1 results)

  • [Journal Article] Mammalian serum albumins as a chiral mediator library for bio-supramolecular photochirogenesis: optimizing enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate.2014

    • Author(s)
      Nishijima, M.; Goto, M.; Fujikawa, M.; Yang, C.; Mori, T.; Wada, T.; Inoue, Y.
    • Journal Title

      Chem. Commun.

      Volume: 50 Issue: 91 Pages: 14082-14085

    • DOI

      10.1039/c4cc04818k

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Circular dichroism spectra of uridine derivatives: ChiraSac study2014

    • Author(s)
      5) T. Miyahara, H. Nakatsuji, T. Wada
    • Journal Title

      J. Phys. Chem. A

      Volume: 118 Issue: 16 Pages: 2931-2941

    • DOI

      10.1021/jp501906u

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Systematic control of the excited-state dynamics and carrier-transport properties of functionalized benzo[ghi]perylene and coronene derivatives2014

    • Author(s)
      S. Hirayama, H. Sakai, Y. Araki, M. Tanaka, M. Imakawa, T. Wada, T. Takenobu, T. Hasobe
    • Journal Title

      Chem.- A Eur. J

      Volume: 20 Issue: 29 Pages: 9081-9093

    • DOI

      10.1002/chem.201304679

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formation of One-Dimensional Helical Columns and Excimerlike Excited States by Racemic Quinoxaline-Fused [7] Carbohelicenes in the Crystal,2014

    • Author(s)
      H. Sakai, S. Shinto, Y. Araki, T. Wada, T. Sakanoue, T. Takenobu, T. Hasobe
    • Journal Title

      Chem. - A Eur. J

      Volume: 20 Issue: 32 Pages: 10099-10109

    • DOI

      10.1002/chem.201402426

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Coordination Oligomers and Polymers of an Oxazole-appended Zinc Chlorophyll Derivative2014

    • Author(s)
      Yoshinao Shinozaki, Isao Yoshikawa, Koji Araki, Kazuaki Ohara, Kentaro Yamaguchi, Shin-ichiro Kawano, Kentaro Tanaka, Yasuyuki Araki, Takehiko Wada, Joe Otsuki
    • Journal Title

      Chemistry Letters

      Volume: 43 Issue: 6 Pages: 862-864

    • DOI

      10.1246/cl.140135

    • NAID

      130004868194

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Electron-Transfer Reduction Properties and Excited-State Dynamics of Benzo[ghi]peryleneimide and Coroneneimide Derivatives2014

    • Author(s)
      T. Hasobe et al
    • Journal Title

      J. Phys. Chem. C

      Volume: 118 Issue: 14 Pages: 7710-7720

    • DOI

      10.1021/jp500761f

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Supramolecular Photocyclodimerization of 2-Hydroxyanthracene with Chiral Hydrogen-Bonding Template, Cyclodextrin and Serum Albumin2014

    • Author(s)
      G. Fukuhara, H. Umehara, S. Higashino, M. Nishijima, C. Yang, T. Mori, T. Wada, Y. Inoue
    • Journal Title

      Photochemical & Photobiological Sciences

      Volume: 13 Issue: 2 Pages: 162-171

    • DOI

      10.1039/c3pp50127b

    • Related Report
      2014 Annual Research Report 2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Double Helices of a Pyridine-Appended Zinc Chlorophyll Derivative2013

    • Author(s)
      Y. Shinozaki, G. Richards, K. Ogawa, A. Yamano, K. Ohara, K. Yamaguchi, S. Kawano, K. Tanaka, Y. Araki, T. Wada, and J. Otsuki
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 135 Issue: 14 Pages: 5262-5265

    • DOI

      10.1021/ja400493e

    • Related Report
      2013 Annual Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Creation of a caspase-3 sensing system using a combination of split-GFP and split-intein2013

    • Author(s)
      Sakamoto, Seiji; Terauchi, Mika; Hugo, Anna; Kim, Tanner; Araki, Yasuyuki; Wada, Takehiko
    • Journal Title

      Chem. Comm.

      Volume: 49 Issue: 87 Pages: 10323-10325

    • DOI

      10.1039/c3cc43389g

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] PNA-NLS conjugates as single-molecular activators of target sites in double-stranded DNA for site-selective scission2013

    • Author(s)
      Y. Aiba, Y. Hamano, W. Kameshima, Y. Araki, T. Wada, A. Accetta, S. Sforza, R. Corradini, R. Marchelli, and M. Komiyama
    • Journal Title

      Org. Biomol. Chem.

      Volume: 11 Issue: 32 Pages: 5233-5238

    • DOI

      10.1039/c3ob40947c

    • NAID

      120007130454

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Bio-Supramolecular Photochirogenesis: Batch-Operated Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate with Human Serum Albumin2013

    • Author(s)
      M. Nishijima, H. Kato, C. Yang, G. Fukuhara, T. Mori, Y. Araki, T. Wada, Y. Inoue
    • Journal Title

      ChemCatChem

      Volume: 5 Issue: 11 Pages: 3237-3240

    • DOI

      10.1002/cctc.201300160

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design and semi-synthesis of photoactivable split-GFP by incorporation of a photocleavable functionality2013

    • Author(s)
      Sakamoto Seiji; Terauchi Mika; Araki Yasuyuki; Wada, Takehiko
    • Journal Title

      Biopolym.

      Volume: 100 Pages: 773-779

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Remarkable Enhancement of Sensitivity with the Second Generation of Elliptically Polarization-detected Circular Dichroism Spectroscopy2013

    • Author(s)
      Murakami, M.; Araki, Y.; Sakamoto, S.; Hamada, Y.; Wada, T.
    • Journal Title

      Chem. Lett

      Volume: 42 Issue: 3 Pages: 261-262

    • DOI

      10.1246/cl.2013.261

    • NAID

      10031155773

    • Related Report
      2013 Annual Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Entrainer Effects on Enantiodifferentiating Photocyclization of 5-Hydroxy-1,1-diphenylpentene in Near- and Supercritical Carbon Dioxide2012

    • Author(s)
      Y. Nishiyama, T. Wada, K. Kakiuchi, Y. Inoue
    • Journal Title

      Journal of Organic Chemistry

      Volume: 77 Issue: 13 Pages: 5681-5686

    • DOI

      10.1021/jo300816w

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design of a dual-color detection system for caspase activities using a combination of split-fluorescent proteins and split-intein2012

    • Author(s)
      Sakamoto, Seiji; Terauchi, Mika; Taki, Shusaku; Kim, Tanner Ian; Araki, Yasuyuki; *Wada, Takehiko
    • Journal Title

      Peptide Sci.

      Volume: 48 Pages: 325-326

    • NAID

      10030204493

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Microenvironmental Control of Enantiodifferentiating Photocyclization of 5-Hydroxy-1,1-diphenylpentene through Selective Solvation2012

    • Author(s)
      Y. Nishiyama, T. Wada, K. Kakiuchi, Y. Inoue
    • Journal Title

      Chirality

      Volume: 24 Issue: 5 Pages: 400-405

    • DOI

      10.1002/chir.22004

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Application of Photoactive Yellow Protein as a Photoresponsive Module for Controlling Hemolytic Activity of Staphylococcal α-Hemolysin2012

    • Author(s)
      M. Ui, et al.
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 39 Pages: 4737-4739

    • DOI

      10.1039/c2cc18118e

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] New paradigm of biomolecular soft-interfaces as chiral reaction fields for supramolecular asymmetric photochirogenesis2012

    • Author(s)
      Wada, Takehiko
    • Journal Title

      Hyomen Kagaku

      Volume: 33 Pages: 27-33

    • NAID

      10030442978

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Presentation] Saturation Transfer Difference(STD)法を用いた血清アルブミ ンと2-アントラセンカルボン酸間相互作用の解析2015

    • Author(s)
      荒木保幸, 西嶋政樹, YOSPANYA Wijak, 奥木暢, 井上佳久, 和田健彦
    • Organizer
      日本化学会 第94春季年会
    • Place of Presentation
      日本大学理工学部
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 生体高分子足場として活用した新規超分子不斉光反応系の構 築-5 ‐ PEG修飾による新規キラル反応場構築2015

    • Author(s)
      奥木暢, 西嶋政樹, 湊 咲絵, 荒木保幸, 坂本清志, 池田豊, 長崎幸夫, 井上佳久, 和田健彦
    • Organizer
      本化学会 第94春季年会
    • Place of Presentation
      日本大学理工学部
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 生体高分子足場として活用した新規超分子不斉光反応系の構築 - 7 - PE G 修飾による超分子不斉光反応への影響 -2014

    • Author(s)
      奥木 暢, 西嶋 政樹, 佐々木 晴彦 , 荒木 保幸, 坂本 清志, 池田 豊, 長崎 幸夫, 井 上 佳久, 和田 健彦
    • Organizer
      2014年光化学討論会
    • Place of Presentation
      北海道大学
    • Year and Date
      2014-10-11 – 2014-10-13
    • Related Report
      2014 Annual Research Report
  • [Presentation] タンパク質を足場とした高分子複合体を活用した超分子不斉光反応系の創成2014

    • Author(s)
      和田 健彦, 奥木 暢, 佐々木 晴彦, 西嶋 政樹, 松田 庸平, 池田 豊, 坂本 清志, 井上 佳久, 荒木 保幸
    • Organizer
      第63回高分子討論会
    • Place of Presentation
      長崎大学
    • Year and Date
      2014-09-24 – 2014-09-26
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 生体高分子足場として活用した 新規超分子不斉反応系の構築2014

    • Author(s)
      奥木暢,西嶋政樹,湊咲絵,荒木保幸,坂本清志,池 田豊,長崎幸夫,井上佳久,和田健彦
    • Organizer
      平成26年度化学系学協会東北大会
    • Place of Presentation
      山形大学
    • Year and Date
      2014-09-20 – 2014-09-21
    • Related Report
      2014 Annual Research Report
  • [Presentation] 生体高分子足場として活用した新規超分子不斉光反応系の構築-6 -PEG修飾HSAを不斉反応場とする超分子不斉光二量化反応-2014

    • Author(s)
      奥木 暢, 西嶋 政樹, 湊 咲絵, 荒木 保幸, 坂本 清志, 池田 豊, 長崎 幸夫, 井上 佳久, 和田 健彦
    • Organizer
      第24回バイオ・高分子シンポジウム
    • Place of Presentation
      東京工業大学
    • Year and Date
      2014-07-24 – 2014-07-25
    • Related Report
      2014 Annual Research Report
  • [Presentation] DEVELOPMENT OF HIGH SENSITIVE AND HIGH TIME-RESOLVED CIRCULAR DICHROISM DETECTION METHOD ? TOWARD THE ANALYSES OF SUPRAMOLECULAR CHIRALITY AND DYNAMICS2014

    • Author(s)
      Takehiko Wada, Makoto Murakami, Yutaka Sano, Yasuyuki Araki, Makoto Kuronuma, Tadashi Mori, Tomoo Miyahara, Katsuji Hasegawa, Hiroshi Nakatsuji, Yoshihisa Inoue
    • Organizer
      XXV IUPAC Symposium on Photochemistry
    • Place of Presentation
      Bordeaux, France
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 生体高分子の機能材料への展開と動的機能制御 ‐がん細胞特異的核酸医薬創製を目指して2013

    • Author(s)
      和田健彦
    • Organizer
      高分子学会中国四国支部-2013年高分子講演会-
    • Place of Presentation
      鳥取大学
    • Year and Date
      2013-12-20
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Development of High Sensitive and Time-resolved Circular Dichroism Detection System –Toward the Analyses of Supramolecular Dynamics –2013

    • Author(s)
      T. WADA
    • Organizer
      2013 Korean-Japan Bilateral Symposium on Frontier Photoscience (2013KJFP)
    • Place of Presentation
      Seoul, Korea
    • Year and Date
      2013-11-25 – 2013-11-28
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 生体高分子の機能材料への展開と動的機能制御2013

    • Author(s)
      和田健彦
    • Organizer
      第61回高分子討論会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2013-09-20
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Development of High Sensitive and Time-resolved Circular Dichroism Detection System –Toward the Analyses of Supramolecular Dynamics –2013

    • Author(s)
      T. Wada
    • Organizer
      Symmetry Festival‐Chirality Section
    • Place of Presentation
      Delft, Netherlands
    • Year and Date
      2013-08-02 – 2013-08-04
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Remarkable Enhancements of Cellular Membrane Uptake Ability and RNase H Activities of Arg Introduced Peptide Ribonucleic Acids (PRNA) and PRNA-DNA Chimera for Cancer Cell Specific Oligonucleotide Therapeutics2013

    • Author(s)
      T. WADA, R. UEMATSU, T. MIZUTANI, J. ARIYOSHI, Y. ARAKI, S. SAKAMOTO, A. YAMAYOSHI, S. Futaki, A. MURAKAMI, Y. INOUE
    • Organizer
      40th Annual Meeting & Exposition of the Controlled Release Society
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2013-07-21 – 2013-07-24
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Novel Strategy of Supramolecular Asymmetric Photochirogenesis with Tailor-made Biopolymers as Chiral Reaction Media2012

    • Author(s)
      Takehiko WADA
    • Organizer
      IUPAC Photochemistry,
    • Place of Presentation
      Coimbra, Portugal
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] 生体高分子の機能材料への展開と動的機能制御2012

    • Author(s)
      和田健彦
    • Organizer
      第61回高分子討論会
    • Place of Presentation
      名古屋, 日本
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] New strategy of supramolecular asymmetric photochirogenesis with biomolecular soft-interfaces as chiral reaction medias2012

    • Author(s)
      Takehiko Wada, Sakie Minato, Yui Sugawara, Masaki Nishijima, Mihoko Ui, Kazushi Kinbara, Kohei Tsumoto, Yasuyuki Araki, Seiji Sakamoto, and Yoshihisa Inoue
    • Organizer
      International Association of Colloid and Interface Scientists2012 (IACIS2012) Conference
    • Place of Presentation
      Sendai, JAPAN
    • Related Report
      2012 Annual Research Report
  • [Book] 光化学の事典、第2章 光化学の基礎Ⅰ ―物理化学― 2.3節 励起状態の環境効果と反応(4) 「光化学における圧力効果」2014

    • Author(s)
      和田健彦
    • Total Pages
      436
    • Publisher
      朝倉書房
    • Related Report
      2014 Annual Research Report

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Published: 2013-05-15   Modified: 2019-07-29  

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