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A glucose-selective fluorescence sensor based on boronic acid-diol recognition
Vishnu Vardhan Karnati1, Xingming Gao, Shouhai Gao
1Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.
Bioorganic & Medicinal Chemistry Letters
|November 7, 2002
Abstract:
A glucose selective diphenylboronic acid fluorescent sensor (10a) with a K(a) of 1472M(-1) has been synthesized and evaluated. This sensor shows a 43- and 49-fold selectivity for glucose over fructose and galactose, respectively. The binding affinity improvement is about 300-fold and the selectivity improvement for glucose over fructose is about 1400-fold compared with the monoboronic acid compound, phenylboronic acid. 1H NMR studies indicate that sensor 10a binds with alpha-D-glucofuranose in a bidentate manner (1:1 ratio).