D3h-Symmetrical Shape-Persistent Macrocycles Consisting of Pyridine–Acetylene–Phenol Conjugates as an Efficient Host Architecture for Saccharide Recognition

Hajime Abe*, Tetsuhiro Yoneda, Yuki Ohishi, Masahiko Inouye

*この論文の責任著者

研究成果: ジャーナルへの寄稿学術論文査読

22 被引用数 (Scopus)

抄録

Hexagonal shape-persistent macrocycles (SPMs) consisting of three pyridine and three phenol rings linked with acetylene bonds were developed as a preorganized host for saccharide recognition by push–pull-type hydrogen bonding. Three tert-butyl or 2,4,6-triisopropylphenyl substituents were introduced on the host to suppress self-aggregation by steric hindrance. In spite of the simple architecture, association constants Kaof the host with alkyl glycoside guests reached the order of 106m−1on the basis of UV/Vis titration experiments. This glycoside recognition was much stronger than that in the cases of acyclic equivalent hosts because of the entropic advantage brought by preorganization of the hydrogen-bonding sites. Solid–liquid extraction and liquid–liquid transport through a liquid membrane were demonstrated by using native saccharides, and much preference to mannose was observed.

本文言語英語
ページ(範囲)18944-18952
ページ数9
ジャーナルChemistry - A European Journal
22
52
DOI
出版ステータス出版済み - 2016/12/23

ASJC Scopus 主題領域

  • 触媒
  • 有機化学

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