The Discrimination of Monosaccharides by 4′-Diphenylamino-4-(1,1′-biphenyl) Boronic Acid

A novel boronic acid fluorescence probe,4′-diphenylamino-4-(1,1′-biphenyl) boronic acid(DBBA),was synthesized with diphenylamine and 4,4′-dibromobiphenyl as material.The probe was used to recognize several saccharides(such as fructose,galactose,glucose and mannose,et al.) in 20%(V/V) ethanol aqueous,and the binding constants of DBBA with all the selected saccharides were determined.The results suggested that this novel boronate has substantial selectivity to fructose.The mechanisms of these recognition process were also explored,and the results demonstrated that the recognization of monosaccharides by DBBA was based on the twisted intramolecular electron transfer(TICT),and DBBA binding with various monosaccharides could induce different degree of inhibition to the TICT system.