A novel type of fluorescent boronic acid that shows large fluorescence intensity changes upon binding with a carbohydrate in aqueous solution at physiological pH

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Abstract

In this paper we report 8-quinolineboronic acid as a novel type of fluorescent probe for carbohydrates. This boronic acid responds to the binding of a carbohydrate with over 40-fold increases in fluorescence intensity and shows optimal fluorescence change at physiological pH in aqueous solution.

8-Quinolineboronic acid was found to exhibit up to about 40-fold increases in fluorescence intensity upon binding with various carbohydrates. It shows optimal fluorescence intensity changes at physiological pH making it a great fluorescent reporter compound for carbohydrate synthesis.

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Acknowledgements

Financial support from the National Institutes of Health (NO1-CO-27184 and CA88343) and the North Carolina Biotechnology Center (2001ARG0016) is gratefully acknowledged. We also thank Professor Jon Lindsey for his help with the quantum yield determination, Dr. Sabapathy Sankar for his help with the 11B NMR experiments, and Dr. Tony Czarnik for helpful discussions.

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