A glucose-selective fluorescence sensor based on boronicacid-diol recognition

A glucose selective diphenylboronic acid fluorescent sensor (10a) with a Ka of 1472 M−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 α- -glucofuranose in a bidentate manner (1:1 ratio).