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Development of Synthetic Oligomers Forming Higher-Order Structures by Self- and Molecular-Recognition Striving for Promotion of Chemical Reactions

Research Project

Project/Area Number 25620129
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Bio-related chemistry
Research InstitutionUniversity of Toyama

Principal Investigator

INOUYE Masahiko  富山大学, 大学院医学薬学研究部(薬学), 教授 (60211752)

Co-Investigator(Kenkyū-buntansha) ABE Hajime  富山大学, 大学院医学薬学研究部(薬学), 准教授 (10324055)
Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsピリジン / フェノール / らせん構造 / 水素結合 / 自己会合 / 糖認識 / 人工オリゴマー
Outline of Final Research Achievements

We have developed "pyridine/phenol oligomer"s consisted of pyridine and phenol units linked at their 2,6-positions with acetylene bonds. The pyridine/phenol alternating 12- and 6-meric oligomers were prepared by Sonogashira reactions and their self-association and saccharide recognition were investigated.
In CDCl3, concentration dependence on 1H NMR spectra revealed that those oligomers show self-association of moderate strength. The Kdim were 350 and 34 M-1 for the 12- and 6-mer, respectively. The 12-mer exhibited much strong saccharide recognition ability. When octyl beta-D-glucopyranoside was added to a DCE solution of the 12-mer, a strong negative CD band was induced, and the Ka was 2.4 x 10^7 M-1. While, the shorter substrate 6-mer showed weaker saccaride recognition, showing a CD band of opposite sign.
These association are based on multipoint hydrogen bonding in a push-pull fashion, which was supported by the X-ray structure of a model compound binding with methanol.

Report

(3 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • Research Products

    (10 results)

All 2015 2014 2013 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 1 results) Presentation (6 results) Remarks (1 results)

  • [Journal Article] A New Class of Structually Simple and Highly Emissive Fluorophores with a Pyridine-Acetylene-Phenol Conjugate2015

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

      Heterocycles

      Volume: 90 Issue: 1 Pages: 515-528

    • DOI

      10.3987/com-14-s(k)51

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Unexpected Chain Length dependence 〓a Chiral rnemory effect of "meta-ethynylpyridine" oligomers2013

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

      Tetrahedron Asymmetry

      Volume: (submitted) Issue: 9-10 Pages: 527-531

    • DOI

      10.1016/j.tetasy.2013.03.019

    • Related Report
      2013 Research-status Report
    • 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

      Volume: 2013 Issue: 9 Pages: 1677-1682

    • DOI

      10.1002/ejoc.201201376

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 水素結合アクセプター性のピリジンとドナー性のフェノールを交互に有すアセチレン連結オリゴマーの糖認識2014

    • Author(s)
      大石雄基・阿部肇・井上将彦
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      宮城県仙台市
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] Development of Hydrogen-Bonding Pyridine-Phenol or -Benzyl Alcohol Alternating Oligomers Linked with Acetylene bonds2014

    • Author(s)
      Yuki Ohishi, Ryuta Yumoto, Hajime Abe, Masahiko Inouye
    • Organizer
      the 9th International Symposium on Macrocyclic and Supramolecular Chemistry
    • Place of Presentation
      Shanghai, China
    • Year and Date
      2014-06-07 – 2014-06-14
    • Related Report
      2014 Annual Research Report
  • [Presentation] 水素結合アクセプターとドナーを交互に持つアセチレン連結オリゴマーの自己会合と糖認識2014

    • Author(s)
      大石雄基・湯元隆太・阿部肇・井上将彦
    • Organizer
      第12回ホスト・ゲスト化学シンポジウム
    • Place of Presentation
      東京都大田区
    • Year and Date
      2014-05-31 – 2014-06-01
    • Related Report
      2014 Annual Research Report
  • [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開発と自己会合評価2014

    • Author(s)
      大石雄基・阿部肇・井上将彦
    • Organizer
      第94日本化学会春季年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
  • [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
    • Related Report
      2013 Research-status Report
  • [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・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
    • Related Report
      2013 Research-status Report
  • [Remarks] 薬化学研究室HP

    • URL

      http://www.pha.u-toyama.ac.jp/yakka/index-j.html

    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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