• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Supramolecular Asymmetric Photochirogenesis with Biopolymers as Chiral Reaction Media

Research Project

Project/Area Number 16H02289
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)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥46,410,000 (Direct Cost: ¥35,700,000、Indirect Cost: ¥10,710,000)
Fiscal Year 2018: ¥7,670,000 (Direct Cost: ¥5,900,000、Indirect Cost: ¥1,770,000)
Fiscal Year 2017: ¥20,930,000 (Direct Cost: ¥16,100,000、Indirect Cost: ¥4,830,000)
Fiscal Year 2016: ¥17,810,000 (Direct Cost: ¥13,700,000、Indirect Cost: ¥4,110,000)
Keywords不斉光反応 / 不斉合成 / 有機光化学 / 超分子化学 / 生体高分子 / タンパク質 / 環境調和型 / 血清アルブミン / 不斉反応 / 高分子修飾 / 超分子 / 環境調和 / 核酸アプタマー / 環境調和型合成 / 有機光反応 / 光不斉反応
Outline of Final Research Achievements

In this study, we tried to construct a supramolecular asymmetric photochirogenesis (SMAP) as a novel asymmetric synthesis utilizing proteins as a chiral reaction media. Asymmetric photoreaction is attracting attention as a new eco-friendly method. The symmetric photodimerization of 2-anthracenecarboxylate (AC) utilizing human serum albumin (HSA) as chiral reaction media was investigated and found to obtain the chiral photodimers with high enantio excesses (ee) up to over 90%. Next, 2,6-anthracene dicarboxylate (AD) was employed as a photo substrate and investigated the SMAP of AD. An unexpected unique photodimer with naphthalene ring, which was never reported in solution synthesis, was obtained with almost 100%ee. Applied this unique reaction for photoreaction of AD with AC, fortunately, the AC-AD heterodimer was obtained with high ee up to 97%. Therefore, in this study, we have successfully demonstrated the SMAP as a powerful "environmentally friendly asymmetric synthesis method."

Academic Significance and Societal Importance of the Research Achievements

新しい超分子光不斉反応(SMAP)系構築に向け、2,6-アントラセンジカルボン酸(AD)のHSA中でのSMAPを検討し、溶液系では得られないナフタレン環を有する特異的な構造の二量体を98%以上の光学収率で得られることを見出した。さらにタンパク質の利点を生かした夾雑系超分子不斉光反応の構築にも取組んだ。その結果、意外にもAC-ADヘテロ二量体が主生成物として97%を超える高いエナンチオ過剰率で得られた。これは、AC-AD間の光反応が動的に起きていると同時に、HSAからの極めて効率よいキラル情報伝搬が達成されていることを示す結果で、従来とは全く異なる超分子不斉光反応系概念の提案に成功した。

Report

(4 results)
  • 2019 Final Research Report ( PDF )
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • Research Products

    (34 results)

All 2020 2019 2018 2017 2016 Other

All Int'l Joint Research (4 results) Journal Article (15 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 15 results,  Open Access: 6 results,  Acknowledgement Compliant: 5 results) Presentation (14 results) (of which Int'l Joint Research: 7 results,  Invited: 11 results) Patent(Industrial Property Rights) (1 results)

  • [Int'l Joint Research] University of Bordeaux(フランス)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] Case Western Reserve University(米国)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] Bordeaux University(France)

    • Related Report
      2017 Annual Research Report
  • [Int'l Joint Research] CaseWesternReserveUniversity(米国)

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Efficient Light‐Harvesting Antennae Resulting from the Dense Organization of Dyes into DNA Junctions though d ‐Threoninol2020

    • Author(s)
      Kashida Hiromu、Azuma Hidenori、Maruyama Ryoko、Araki Yasuyuki、Wada Takehiko、Asanuma Hiroyuki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: - Issue: 28 Pages: 11360-11363

    • DOI

      10.1002/anie.202004221

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Underwater Bubble and Oil Repellency of Biomimetic Pincushion and Plastron-Like Honeycomb Films2020

    • Author(s)
      Chen Bihai、Wada Takehiko、Yabu Hiroshi
    • Journal Title

      Langmuir

      Volume: 36 Issue: 23 Pages: 6365-6369

    • DOI

      10.1021/acs.langmuir.0c00427

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Reversible Changes in the Orientation of Gold Nanorod Arrays on Polymer Brushes2020

    • Author(s)
      Sekizawa Yu、Mitomo Hideyuki、Nihei Mizuki、Nakamura Satoshi、Yonamine Yusuke、Kuzuya Akinori、Wada Takehiko、Ijiro Kuniharu
    • Journal Title

      Nanoscale Advances

      Volume: 2 Issue: 9 Pages: 3798-3803

    • DOI

      10.1039/d0na00315h

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Solvent Effects and Aggregation Phenomena Studied by Vibrational Optical Activity and Molecular Dynamics: The Case of Pantolactone2020

    • Author(s)
      Ghidinelli Simone、Abbate Sergio、Koshoubu Jun、Araki Yasuyuki、Wada Takehiko、Longhi Giovanna
    • Journal Title

      The Journal of Physical Chemistry B

      Volume: 124 Issue: 22 Pages: 4512-4526

    • DOI

      10.1021/acs.jpcb.0c01483

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] 1.Development of an Engineered Photoactive Yellow Protein as a Cross-Linking Junction for Construction of Photoresponsive Protein-Polymer Conjugates2019

    • Author(s)
      Ui, Mihoko; Miyauchi, Yusuke; Inoue, Masataka; Murakami, Makoto; Araki, Yasuyuki; Wada, Takehiko; Kinbara, Kazushi
    • Journal Title

      ChemPhotoChem

      Volume: 3 Issue: 6 Pages: 356-360

    • DOI

      10.1002/cptc.201900024

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Peptide Ribonucleic Acid (PRNA)-Arginine Hybrids. Effects of Arginine Residues Alternatingly Introduced to PRNA Backbone on Aggregation, Cellular Uptake, and Cytotoxicity2018

    • Author(s)
      Sugai, Hiroka; Nakase, Ikuhiko; Sakamoto, Seiji; Nishio, Akihito; Nishijima, Masaki; Yamayoshi, Asako; Araki, Yasuyuki; Ishibashi, Satoru; Yokota, Inoue, Yoshihisa; Wada, Takehiko,*
    • Journal Title

      Chemistry Letters

      Volume: 47 Issue: 3 Pages: 381-384

    • DOI

      10.1246/cl.171186

    • NAID

      130006434142

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Control of the electrochemical and photophysical properties of N-substituted benzo[ghi]perylene derivatives2017

    • Author(s)
      Tokuo Kokichi、Sakai Hayato、Sakanoue Tomo、Takenobu Taishi、Araki Yasuyuki、Wada Takehiko、Hasobe Taku
    • Journal Title

      Materials Chemistry Frontiers

      Volume: 1 Issue: 11 Pages: 2299-2308

    • DOI

      10.1039/c7qm00301c

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Recent Topics of Bioimagings2017

    • Author(s)
      Hirano, Takashi; Wada, Takehiko
    • Journal Title

      Journal of Photochemistry and Photobiology, C: Photochemistry Reviews

      Volume: 30 Pages: 1-2

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Regioselective Molecularly Imprinted Reaction Field for [4 + 4] Photocyclodimerization of 2-Anthracenecarboxylic Acid2017

    • Author(s)
      Nakai Satoshi; Sunayama Hirobumi; Kitayama Yukiya; Takeuchi Toshifumi; Nishijima Masaki; Inoue Yoshihisa; Wada Takehiko
    • Journal Title

      Langmuir

      Volume: 33 Issue: 9 Pages: 2103-2108

    • DOI

      10.1021/acs.langmuir.6b04104

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective and robust stabilization of triplex DNA structures using cationic comb-type copolymer2017

    • Author(s)
      A. Yamayoshi, D. Miyoshi, Y. Zouzumi, Y. Matsuyama, J. Ariyoshi, N. Shimada, A. Murakami, T. Wada, A. Maruyama
    • Journal Title

      J. Phys. Chem., B

      Volume: 1221 Issue: 16 Pages: 4015-4022

    • DOI

      10.1021/acs.jpcb.7b01926

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthetic Control of Photophysical Process and Circularly Polarized Luminescence of [5]Carbohelicene Derivatives Substituted by Maleimide Units2016

    • Author(s)
      Hayato Sakai, Takako Kubota, Junpei Yuasa, Yasuyuki Araki, Tomo Sakanoue, Taishi Takenobu, Takehiko Wada, Tsuyoshi Kawai, and Taku Hasobe
    • Journal Title

      Journal of Phyisical Chemistry C

      Volume: 120 Issue: 14 Pages: 7860-7869

    • DOI

      10.1021/acs.jpcc.6b01344

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Protonation-Induced Red-Coloured Circularly Polarized Luminescence of [5]Carbohelicene Fused by Benzimidazole2016

    • Author(s)
      H. Sakai, T. Kubota, J. Yuasa, Y. Araki, T. Sakanoue, T. Takenobu, T. Wada, T. Kawai, T. Hasobe
    • Journal Title

      Org. Biomol. Chem.

      Volume: 14 Issue: 28 Pages: 6738-6743

    • DOI

      10.1039/c6ob00937a

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Activation of p53 facilitates the target search in DNA by enhancing the target recognition probability2016

    • Author(s)
      Itoh Y., Murata A., Sakamoto S., Nanatani K., Wada T., Takahashi S., Kamagata K.
    • Journal Title

      J. Mol. Biol.

      Volume: 428 Issue: 14 Pages: 2916-2930

    • DOI

      10.1016/j.jmb.2016.06.001

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Controllable Electronic Structures and Photoinduced Processes of Bay-Linked Perylenediimide Dimers and Ferrocene-Linked Triad2016

    • Author(s)
      H. Horinouchi, H. Sakai, Y. Araki, T. Sakanoue, T. Takenobu, T. Wada, N. V. Tkachenko, T. Hasobe
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Issue: 28 Pages: 9631-9641

    • DOI

      10.1002/chem.201601058

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Highly Enantiodifferentiating Site of Human Serum Albumin for Mediating Photocyclodimerization of 2-Anthracenecarboxylate Elucidated by Site-Specific Inhibition/Quenching with Xenon2016

    • Author(s)
      Nishijima, M.; Pace, T. C. S.; Bohne, C.; Mori, T.; Inoue, Y.; Wada, T.
    • Journal Title

      J. Photochem. Photobiol. A

      Volume: 331 Pages: 89-94

    • DOI

      10.1016/j.jphotochem.2015.12.019

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] 細胞内環境応答型人工核酸システムの開発 ‐ヌクレアーゼ活性制御機能を有する癌細胞選択的核酸医薬創製を目指して‐2020

    • Author(s)
      和田健彦
    • Organizer
      長崎大学大学院医歯薬学総合研究科 第3回機能性分子化学フォーラム
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Development of high sensitive and high time-resolve circular dichroism (CD) measurement system2019

    • Author(s)
      Takehiko WADA
    • Organizer
      Advances in Noncanonical Nucleic Acids 2019 (ANNA2019)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of Intracellular Condition Responsive Artificial Nucleic Acids for the Catalytic Oligonucleotide Therapeutics2019

    • Author(s)
      Takehiko WADA
    • Organizer
      6th Annual Joint Data Science in Life Science and Engineering Symposium
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 弱い相互作用を協働的に活用した不斉光反応制御 ‐生体高分子をキラル反応場として活用した超分子不斉光反応系を中心として‐2019

    • Author(s)
      和田健彦
    • Organizer
      第40回光化学若手の会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 天然ヌクレアーゼ活性超越に資するDNA-人工核酸キメラ分子構造設計と機能評価2019

    • Author(s)
      和田健彦
    • Organizer
      第68回高分子討論会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] CREATION OF CANCER CELL SPECIFIC OLIGONUCLEOTIDE THERAPEUTICS SYSTEM WITH INTRACELLULAR CONDITION RESPONSIVE FUNCTIONAL POYMERS: ARTIFICIAL NUCLEIC ACIDS NAMED PEPTIDE RIBONUCLEIC ACIDS (PRNA)2017

    • Author(s)
      Takehiko WADA
    • Organizer
      East Asian Symposium on Polymers for Advanced Technologies 2017 (EASPAT-2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Creation of Hypoxia/Ischemia (Cancer) Cell Specific Oligonucleotide Therapeutics System with Intracellular Environmental Condition Responsive Peptide Ribonucleic Acids (PRNAs)2017

    • Author(s)
      Takehiko WADA
    • Organizer
      Special Lecture of Institute of Biological Chemistry, Academia Sinica, Taipei, Taiwan
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Creation of Cancer Cell Specific Oligonucleotide Therapeutics System with Intracellular Environmental Condition Responsive Peptide Ribonucleic Acids (PRNAs)2017

    • Author(s)
      Takehiko WADA
    • Organizer
      International Conference on Advanced Polymer Science and Technology (2017ICAPST, National Chung Hsing Univ (NCHU), Taichung, Taiwan
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Supramolecular asymmetric photochirogenesis mediated by synthetic antibody: asymmetric photocyclodimerization of 2-anthracenecarboxylate mediated by synthetic scFv antibody2017

    • Author(s)
      Wijak Yospanya, Seiji Sakamoto, Yasuyuki Araki, Masaki Nishijima, Yoshihisa Inoue, Takehiko Wada
    • Organizer
      28th International Conference on Photochemistry (ICP 2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] MMP応答型 PEG 複合化ペプチドを用いたがん選択的細胞内送達システムの開発と細胞機能制御への応用2017

    • Author(s)
      和田健彦
    • Organizer
      第66回高分子討論会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] タンパク質を不斉反応場とする2-アントラセンカルボン酸な らびに2,6-アントラセンジカルボン酸の超分子不斉光反応の検討2016

    • Author(s)
      豊岡 壮太, 西嶋 政樹, 坂本 清志 , 荒木 保幸, 井上 佳久, 和田 健彦
    • Organizer
      第65回高分子討論会
    • Place of Presentation
      神奈川大学(神奈川県横浜市)
    • Year and Date
      2016-09-14
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 血清アルブミンを不斉反応場とする 2-アントラセンカルボン酸ならびに 2,6-アント ラセンジカルボン酸の超分子不斉光反応の検討2016

    • Author(s)
      豊岡 壮太, 西嶋 政樹, 荒木 保幸, 坂本 清志, 井上 佳久,和田 健彦
    • Organizer
      2016年光化学討論会
    • Place of Presentation
      東京大学駒場キャンパス(東京都目黒区)
    • Year and Date
      2016-09-06
    • Related Report
      2016 Annual Research Report
  • [Presentation] Supramolecular asymmetric photochirogenesis mediated by synthe tic antibody: The effect of the temperature, pH and ionic strength upon [4+4] enantiodiffer entiating photodimerization of 2-anthracenecarboxylate media ted by synthetic scFv antibody2016

    • Author(s)
      W .Yospanya, S. Sakamoto, Y. Araki, M. Nishijima, Y. Inoue, T. Wada
    • Organizer
      2016年光化学討論会
    • Place of Presentation
      東京大学駒場キャンパス(東京都目黒区)
    • Year and Date
      2016-09-06
    • Related Report
      2016 Annual Research Report
  • [Presentation] SUPRAMOLECULAR ASYMMETRIC PHOTOCHIROHGEBESIS (SMAP) OF 2-ANTHRACENECARBOXYLATE (AC) WITH PROTEINS AND PROTEIN-POLYMER HYBRIDS AS CHIRAL REACTION MEDIAS – PEGYLATION OF HAS/BSA AND SMAP OF AC MEDIATED BY PEG-HAS/BSA2016

    • Author(s)
      Mitsuru Okugi, Haruhiko Sasaki, Souta Toyooka, Nishijima Masaki, Yasuyuki Araki, Seiji Sakamoto, Yoshihisa Inoue, Takehiko Wada
    • Organizer
      The 26th IUPAC Symposium on Photochemistry
    • Place of Presentation
      Osaka City Central Public Hall (Kita-ku, Osaka)
    • Year and Date
      2016-04-06
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Patent(Industrial Property Rights)] ・ キメラ分子、医薬組成物、標的核酸の切断方法、及び標的核酸切断用又は診断用キット2019

    • Inventor(s)
      和田健彦
    • Industrial Property Rights Holder
      和田健彦
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Related Report
      2018 Annual Research Report

URL: 

Published: 2016-04-21   Modified: 2022-10-07  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi