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2013 Fiscal Year Final Research Report

Development of Synthetic Host Molecule Aiming to Artificial Enzymes for Sugar Synthesis

Research Project

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Project/Area Number 23655124
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Functional materials chemistry
Research InstitutionUniversity of Toyama

Principal Investigator

ABE Hajime  富山大学, 大学院医学薬学研究部(薬学), 准教授 (10324055)

Co-Investigator(Renkei-kenkyūsha) INOUYE Masahiko  富山大学, 大学院・医学薬学研究部, 教授 (60211752)
Project Period (FY) 2011 – 2013
Keywordsエチニルピリジン / 大環状化合物 / ピリジン / フェノール / 糖 / ホスト・ゲスト化学 / 薗頭反応
Research Abstract

Pyridine-phenol alternating macrocyclic oligomers, which were designed for strong saccharide recognition ability, have been developed in this research. The qualitative study on 1H NMR and DFT calculation studies suggested that the saccharide recognition ability is much stronger than we expected before the project. However, the self-aggregation of the host was a serious problem for saccharide recognition. So the effect of steric hindrance was examined by introducing tert-butyl and 2,4,6-triisopropylphenyl groups on the host macrocycle. Finally, it was found that the association constant between the host and octyl glucoside achieved up to 900,000 /M.

  • Research Products

    (25 results)

All 2014 2013 2012 2011

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (15 results) (of which Invited: 1 results)

  • [Journal Article] Alternating 2, 6-/3, 5-Substituted Pyridine-Acetylene Macrocycles : π-Stacking Self-Assemblies Enhanced by Intermolecular Dipole-Dipole Interaction2014

    • Author(s)
      Abe, H.; Ohtani, K.; Suzuki, D.; Chida, Y.; Shimada, Y.; Matsumoto, Y.; Inouye, M
    • Journal Title

      Org. Lett

      Volume: 16 Pages: 828-831

    • DOI

      10.1021/ol403579e

    • Peer Reviewed
  • [Journal Article] Preparation and Spectroscopic Study of Alternate meta-Ethynylpyridine Oligomer Involving 2, 4, 6-Trisubstituted and 3, 5-Disubstituted Pyridine Rings2014

    • Author(s)
      Abe, H.; Suzuki, D.; Shimizu, A.; Inouye, M.
    • Journal Title

      Heterocycles

      Volume: 88 Pages: 547-557

    • DOI

      10.3987/COM-13-S(S)78

    • Peer Reviewed
  • [Journal Article] Unexpected chain length dependence on a chiral memory effect of "meta-ethynylpyridine" oligomers2013

    • Author(s)
      Takashima, S.; Abe, H.; Inouye, M
    • Journal Title

      Tetrahedron : Asymmetry

      Volume: 24 Pages: 527-531

    • DOI

      10.1016/j.tetasy.2013.03.019

    • Peer Reviewed
  • [Journal Article] Stabilization of Chiral Helices for Saccharide-Linked Ethynylpyridine Oligomers Possessing a Conformationally Well-Defined Linkage2013

    • Author(s)
      Kayamori, F.; Abe, H.; Inouye, M
    • Journal Title

      Eur. J. Org. Chem

      Pages: 1677-1682

    • DOI

      10.1002/ejoc.201201376

    • Peer Reviewed
  • [Journal Article] Improvement of Helix-Forming Ability of Mannoside-Linked Ethynylpyridine Oligomers Constructed by Convergent Synthesis2012

    • Author(s)
      Abe, H.; Makida, H.; Inouye, M
    • Journal Title

      Heterocycles

      Volume: 86 Pages: 955-963

    • DOI

      10.3987/COM-12-S(N)97

    • Peer Reviewed
  • [Journal Article] Formation of Higher-Order Structures of Chiral Poly(ethynylpyridine)s Depending on Size, Temperature, and Saccharide Recognition2012

    • Author(s)
      Abe, H.; Okada, K.; Makida, H.; Inouye, M
    • Journal Title

      Org. Biomol. Chem

      Volume: 10 Pages: 6930-6936

    • DOI

      10.1039/C2OB25816A

    • Peer Reviewed
  • [Journal Article] Concentration- and Time-Dependent Eccentric Changes in Circular Dichroism of Saccharide-Linked Ethynylpyridine Oligomer with Copper(II) Ions2012

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

      J. Org. Chem

      Volume: 77 Pages: 5209-5214

    • DOI

      10.1021/jo300735j

    • Peer Reviewed
  • [Journal Article] Development of Convergent Synthetic Method for Saccharide-Linked Ethynylpyridine Foldamers by Huisgen Reaction2012

    • Author(s)
      Abe, H.; Makida, H.; Inouye, M
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 4353-4361

    • DOI

      10.1016/j.tet.2012.02.069

    • Peer Reviewed
  • [Journal Article] Copper(II)/phenanthroline-mediated CD-enhancement and Chiral Memory Effect on meta-Ethynylpyridine Oligomer2012

    • Author(s)
      Takashima, S.; Abe, H.; Inouye, M
    • Journal Title

      Chem. Commun

      Volume: 48 Pages: 3330-3332

    • DOI

      10.1039/C2CC00063F

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Selective and Sequential Functionalization of 2, 4, 6-Trihalopyridine Rings : Synthesis of Ethynylpyridine Polymers Directly Joined with aza-Crown Ethers2012

    • Author(s)
      Takashima, S.; Yamamoto, T.; Abe, H.; Inouye, M
    • Journal Title

      Heterocycles

      Volume: 84 Pages: 355-360

    • DOI

      10.3987/COM-11-S(P)62

    • Peer Reviewed
  • [Presentation] 多点水素結合能を有するピリジン-フェノール交互型コオリゴマーの開発と自己会合評価2014

    • Author(s)
      大石雄基・阿部肇・井上将彦
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Year and Date
      20140327-30
  • [Presentation] 最強のグルコース受容体を目指して"de novo"設計されたピリジン-フェノール交互マクロサイクルの開発2013

    • Author(s)
      河濟悠生・阿部肇・井上将彦
    • Organizer
      平成25年度有機合成化学北陸セミナー
    • Place of Presentation
      金沢
    • Year and Date
      20131004-05
  • [Presentation] 自己相補的水素結合能を有するピリジン-フェノール交互型オリゴマーの二重らせん形成2013

    • Author(s)
      大石雄基・阿部肇・井上将彦
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      東京
    • Year and Date
      20130905-07
  • [Presentation] 多点水素結合能を有するピリジン-フェノール交互型オリゴマーの合成と性質2013

    • Author(s)
      大石雄基・河濟悠生・阿部肇・井上将彦
    • Organizer
      第10回ホスト・ゲスト化学シンポジウム
    • Place of Presentation
      和歌山
    • Year and Date
      20130525-26
  • [Presentation] アセチレン連結ピリジン-フェノール交互型オリゴマーの自己相補的水素結合能の評価2013

    • Author(s)
      大石雄基・河濟悠生・阿部肇・井上将彦
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀・草津
    • Year and Date
      20130322-25
  • [Presentation] Development of Alternating Cooligomers of Pyridine and Phenol Rings Linked with Acetylene Bonds2012

    • Author(s)
      Ohishi, Y.; Kawasumi, H.; Abe, H.; Inouye, M
    • Organizer
      The Twelfth International Kyoto Conference on New Aspect of Organic Chemistry (IKCOC-12)
    • Place of Presentation
      Kyoto
    • Year and Date
      20121112-16
  • [Presentation] 自己相補的水素結合能を有するピリジン-フェノール交互型オリゴマーの合成と物性2012

    • Author(s)
      大石雄基・河濟悠生・阿部肇・井上将彦
    • Organizer
      平成24年度有機合成化学北陸セミナー
    • Place of Presentation
      富山
    • Year and Date
      20121005-06
  • [Presentation] アセチレンを介してピリジンとフェノールが連結した交互オリゴマーの開発2012

    • Author(s)
      大石雄基・河濟悠生・阿部肇・井上将彦
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都
    • Year and Date
      20120919-21
  • [Presentation] 水素結合性エチニルピリジン分子とその糖認識作用2012

    • Author(s)
      阿部肇
    • Organizer
      第44回構造有機化学若手の会 夏の学校
    • Place of Presentation
      札幌
    • Year and Date
      20120802-04
    • Invited
  • [Presentation] 水素結合性大環状エチニルピリジンオリゴマーによる糖認識2012

    • Author(s)
      阿部肇・河濟悠生・大谷航平・井上将彦
    • Organizer
      第9回ホスト・ゲスト化学シンポジウム
    • Place of Presentation
      札幌
    • Year and Date
      20120526-27
  • [Presentation] D3h対称性エチニルピリジンオリゴマーの合成と物性2012

    • Author(s)
      大谷航平・阿部肇・井上将彦
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Year and Date
      20120325-28
  • [Presentation] 芳香族-アセチレン骨格を連ねた水素結合性大環状ホスト分子の合成と糖認識能2012

    • Author(s)
      阿部肇・河濟悠生・井上将彦
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学矢上キャンパス 横浜市
    • Year and Date
      20120325-28
  • [Presentation] ピリジン-フェノール交互型オリゴマーの合成と自己相補的水素結合能の評価2012

    • Author(s)
      大石雄基・河濟悠生・阿部肇・井上将彦
    • Organizer
      日本薬学会北陸支部第124回例会
    • Place of Presentation
      富山
    • Year and Date
      2012-11-18
  • [Presentation] 剛直かつ対称なエチニルピリジン大環状分子の合成と糖認識機能2011

    • Author(s)
      阿部肇・大谷航平・河濟悠生・千田祐資・井上将彦
    • Organizer
      第22回基礎有機化学討論会
    • Place of Presentation
      つくば
    • Year and Date
      20110921-23
  • [Presentation] 大環状エチニルピリジン分子による二糖の選択的分子認識2011

    • Author(s)
      阿部肇・千田祐資・井上将彦
    • Organizer
      モレキュラー・キラリティー2011
    • Place of Presentation
      東京
    • Year and Date
      20110520-21

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Published: 2015-06-25  

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