"Click-fluors": Triazole-linked saccharide sensors

Wenlei Zhai, Brette M. Chapin, Akina Yoshizawa, Hui Chen Wang, Stephen A. Hodge, Tony D. James, Eric V. Anslyn, John S. Fossey

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A series of boronic acid-containing saccharide receptors was synthesised via copper catalysed azide-alkyne cycloaddition (CuAAC) reactions. Their saccharide binding capacity was studied by 1H and 11B NMR spectroscopy titrations and isothermal titration calorimetry (ITC) techniques. Fluorescent sensors were generated by linking a phenylboronic acid (PBA) receptor with fluorophores via a triazole-linker. Fluorescence titrations with fructose revealed that the substitution pattern about the PBA influences the fluorescence response to saccharides. Titrations studied by 1H NMR spectroscopy suggested that fructose binding is enhanced when the aromatic ring bearing the boronic acid has the triazole-containing substituent at the ortho position. No evidence of either a dative N-B bond or solvent insertion (between B and N) was observed by 11B NMR spectroscopy. These results demonstrate that synthetic accessible triazole receptors may allow rapid sensor synthesis, screening and discovery.

Original languageEnglish
Pages (from-to)918-928
Number of pages11
JournalOrganic Chemistry Frontiers
Volume3
Issue number8
Early online date14 Jun 2016
DOIs
Publication statusPublished - 1 Aug 2016

ASJC Scopus subject areas

  • Organic Chemistry

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