Spectroscopic sugar sensing by a stilbene derivative with push (Me2N-)-pull ((HO)2B-)-type substituents

Hideyuki Shinmori, Masayuki Takeuchi, Seiji Shinkai

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Abstract

A stilbene derivative (2) with a push (Me2N-) and a pull ((HO)2B-) substituent at 4,4′-positions was synthesized. 2 aggregated in aqueous solution (water:DMSO = 30:1 v/v) but was dispersed nearly homogeneously in water:DMSO = 1:1 v/v. Spectroscopic studies established that 2 is useful to detect saccharides by both absorption and fluorescence spectroscopic methods. Particularly, in aqueous solution at pH 8.0 a large increase in the fluorescence intensity was observed upon complexation with D-fructose. This is a novel sugar sensing system using boronic acid as an interface.

Original languageEnglish
Pages (from-to)1893-1902
Number of pages10
JournalTetrahedron
Volume51
Issue number7
DOIs
Publication statusPublished - Feb 13 1995

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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