Preferential Binding to a Mannoside of a Pyridine–Acetylene–Phenol Macrocycle with a Fluorine Substituent in the Cavity

Yuki Ohishi*, Junya Chiba, Masahiko Inouye

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

We developed a pyridine–acetylene–phenol macrocycle in which a fluorine atom was introduced in place of a hydroxy group, as a host for the selective binding to epimers of glucose. The fluorine atom was expected to work as a negatively charged infill repelling oxygen atoms of saccharides and prevent the efficient formation of a hydrogen-bond network with a glucoside, whose cross-section size is larger than those of the corresponding epimers, especially of a mannoside. UV–Vis and fluorescence titration experiments revealed that this host showed a higher affinity for a mannoside than a glucoside. 1H NMR and molecular modeling suggested that the fluorine atom acts as a moderate infill weakening the binding to a glucoside. This result indicates that selectivity for guest molecules can be modified by replacing a hydroxy group and a hydrogen atom in host molecules with a fluorine atom.

Original languageEnglish
Article numbere202400758
JournalEuropean Journal of Organic Chemistry
Volume27
Issue number45
DOIs
StatePublished - 2024/12/02

Keywords

  • Fluorine
  • Hydrogen bonds
  • Macrocycles
  • Molecular recognition
  • Saccharides

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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