"click-fluors": Triazole-linked saccharide sensors

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Organic Chemistry Frontiers, ISSN: 2052-4129, Vol: 3, Issue: 8, Page: 918-928

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Wenlei Zhai; Brette M. Chapin; Akina Yoshizawa; Hui Chen Wang; John S. Fossey; Eric V. Anslyn; Stephen A. Hodge; Tony D. James
Royal Society of Chemistry (RSC); The Royal Society of Chemistry
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article description
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 H and B 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 H 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 B NMR spectroscopy. These results demonstrate that synthetic accessible triazole receptors may allow rapid sensor synthesis, screening and discovery.