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Chirality Fixation and Improbement of Sugar-Recognizing Helical Oligomers

Research Project

Project/Area Number 17K05927
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Bio-related chemistry
Research InstitutionHimeji Dokkyo University (2018-2019)
University of Toyama (2017)

Principal Investigator

Abe Hajime  姫路獨協大学, 薬学部, 教授 (10324055)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsピリジン / フェノール / ジフルオロメチル / アリールアセチレンオリゴマー / 水素結合 / 糖認識 / らせん / 超分子化学 / ホストゲスト化学 / らせん分子 / アルケンメタセシス
Outline of Final Research Achievements

We have worked on development of "pyridine-phenol alternating oligomer" and "difluoromethyl-containing oligomer" at Toyama University (in 2017) and at Himeji Dokkyo University (in 2018-2019). In their molecular design, we aimed to form a chiral helical higher-order structure by molecular recognition, followed by the structure stabilization. In the process of synthesis and evaluating the function, we succeeded to obtain "pyridine-phenol alternating oligomer" with alkenyl side chains, and while making a chiral helix with sugar, the higher-order structure could be stabilized by alkene metathesis. With regard to "difluoromethyl-containing oligomers", we have developed a synthetic procedure for building blocks and achieved the oligomers of a certain length.

Academic Significance and Societal Importance of the Research Achievements

らせん型の構造は、核酸や蛋白質にも見られるなど、機能的な高次構造のひとつである。本研究では、官能基を持つ芳香環をアセチレン結合を介してつないでいったオリゴマーを設計、合成し、官能基による分子認識と、らせん型構造の形成、安定化を狙った。ピリジン環とフェノール環を交互につないだ「ピリジン-フェノール交互型オリゴマー」、官能基としてジフルオロメチル基を持たせた「ジフルオロメチル含有オリゴマー」を設計した。前者のオリゴマーでは、合成法の確立および糖質の添加によるキラルならせん構造の構築、およびその安定化に成功した。後者では、ビルディングブロックの合成法の確立と、一定の鎖長のオリゴマーの合成まで進んだ。

Report

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

    (14 results)

All 2020 2019 2018 2017

All Journal Article (8 results) (of which Peer Reviewed: 8 results,  Open Access: 1 results) Presentation (6 results) (of which Int'l Joint Research: 2 results,  Invited: 2 results)

  • [Journal Article] Preferential Recognition and Extraction to Pentoses over Hexoses by a D6h-Symmetrical Ethynylphenol Macrocycle with Six Inner Phenolic Hydroxy Groups2020

    • Author(s)
      Hayashi, T.; Ohishi, Y.; Abe, H.; Inouye, M.
    • Journal Title

      J. Org. Chem.

      Volume: 85 Issue: 4 Pages: 1927-1934

    • DOI

      10.1021/acs.joc.9b02639

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Aromatic Foldamers Recognizing Saccharides to Form Chiral Helices2019

    • Author(s)
      Abe Hajime
    • Journal Title

      YAKUGAKU ZASSHI

      Volume: 139 Issue: 4 Pages: 591-598

    • DOI

      10.1248/yakushi.18-00179-2

    • NAID

      130007621599

    • ISSN
      0031-6903, 1347-5231
    • Year and Date
      2019-04-01
    • Related Report
      2019 Annual Research Report 2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Solid-Liquid Extraction of Native Saccharides with Chiral BINOL-Based Pyridine-Phenol Type Macrocycles2019

    • Author(s)
      Ohishi, Y.; Murase, M.; Abe, H.; Inouye, M.
    • Journal Title

      Org. Lett.

      Volume: 21 Issue: 16 Pages: 6202-6207

    • DOI

      10.1021/acs.orglett.9b01980

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nonplanar Macrocycle Consisting of Four Pyridine and Phenol Units Connected with Acetylene Bonds Displaying Preferential Binding to Maltoside over Monosaccharides2018

    • Author(s)
      Ohishi Yuki、Yamamoto Naoto、Abe Hajime、Inouye Masahiko
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 83 Issue: 10 Pages: 5766-5770

    • DOI

      10.1021/acs.joc.8b00062

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Metathesis-Based Stapling of a Pyridine-Acetylene-Phenol Oligomer Having Alkenyl Side Chains after Intermolecular Templation by Native Saccharides2018

    • Author(s)
      Abe Hajime、Sato Chihiro、Ohishi Yuki、Inouye Masahiko
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2018 Issue: 24 Pages: 3131-3138

    • DOI

      10.1002/ejoc.201800531

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Hexaphenolic Rigid Cages Prepared by Self-Organization of C3v Tridentates2018

    • Author(s)
      Hajime Abe; Daisuke Hashikawa; Takaya Minami; Kohei Ohtani; Kentaro Masuda; Shinya Matsumoto; Masahiko Inouye
    • Journal Title

      J. Org. Chem.

      Volume: 83 Issue: 6 Pages: 3132-3141

    • DOI

      10.1021/acs.joc.7b03111

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Preparation and Higher-order Structures of 2,6-Pyridylene and 2,6-Pyrazylene Alternating Macrocycle with the Inner Nitrogen Atoms in All the Aromatic Rings2017

    • Author(s)
      Daiki Suzuki; Hajime Abe; Takaya Minami; Shinya Matsumoto; Masahiko Inouye
    • Journal Title

      Chem. Lett.

      Volume: 46 Issue: 12 Pages: 1740-1742

    • DOI

      10.1246/cl.170815

    • NAID

      130006243212

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Saccharide Recognition and Helix Formation in Water with an Amphiphilic Pyridine-Phenol Alternating Oligomer2017

    • Author(s)
      Yuki Ohishi; Hajime Abe; Masahiko Inouye
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2017 Issue: 46 Pages: 6975-6979

    • DOI

      10.1002/ejoc.201701522

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] トリアリールメシチレン型ホスト分子の開発2019

    • Author(s)
      阿部肇・中里 佳澄・藤江 直巳・浅山 範久・坂部 拓哉
    • Organizer
      第17回ホスト・ゲスト・超分子化学シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] BINOL構造を導入したピリジン-アセチレン-フェノール大環状ホスト分子によるエナンチオ選択的な天然糖認識2019

    • Author(s)
      大石 雄基・村瀬 実希乃・阿部 肇・井上 将彦
    • Organizer
      第17回ホスト・ゲスト・超分子化学シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] "meta"-エチニルフェノール大環状ホスト分子の合成とそのサイズ選択的なゲスト認識2019

    • Author(s)
      林 友哉・大石 雄基・阿部 肇・井上 将彦
    • Organizer
      第17回ホスト・ゲスト・超分子化学シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] Arylene Ethynylene Foldamers with Pyridine and/or Phenol Units2019

    • Author(s)
      Hajime Abe
    • Organizer
      Workshop on Aromatic Foldamers
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Tridental Tetraarene Receptor for Hydroxy Guests2018

    • Author(s)
      Hajime Abe
    • Organizer
      The Third International Symposium on Toyama-Asia-Africa Pharmaceutical Network (TAA)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of Pyridine-Acetylene-Phenol Helical Oligomers Cross-Linked by Alkene Metathesis at Side Chains2017

    • Author(s)
      Chihiro Sato, Yuki Ohishi, Hajime Abe, and Masahiko Inouye
    • Organizer
      29th International Symposium on Chirality (Chirality 2017; ISCD-29)
    • Related Report
      2017 Research-status Report

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Published: 2017-04-28   Modified: 2021-02-19  

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