ja073939u_si_001.pdf (144.21 kB)
Boronic Acid Based Peptidic Receptors for Pattern-Based Saccharide Sensing in Neutral Aqueous Media, an Application in Real-Life Samples
journal contributionposted on 2007-11-07, 00:00 authored by Nicola Y. Edwards, Thomas W. Sager, John T. McDevitt, Eric V. Anslyn
The advent of the alternative sweeteners market has signaled a demand for chemosensors which target multiple saccharides and saccharide derivatives, in aqueous media at physiological pH. This demand has largely been unmet as existing molecular receptors for saccharides have generally not shown sufficient degrees of affinity and selectivity in aqueous media. A chemosensor array for saccharides and saccharide derivatives, fully operational in aqueous media at physiological pH, has been developed and is reported herein. Boronic acid based peptidic receptors, derived from a combinatorial library, served as the cross-reactive sensor elements in this array. The binding of saccharides to these receptors was assessed colorimetrically using an indicator uptake protocol in the taste-chip platform. The differential indicator uptake rates of these receptors in the presence of saccharides were exploited in order to identify patterns within the data set using linear discriminant analysis. This chemosensor array is capable of classifying disaccharides and monosaccharides as well as discriminating compounds within each saccharide group. Disaccharides have also been distinguished from closely related reduced-calorie counterparts. This linear discriminant analysis set was then employed as a training set for identifying a specific saccharide in a real-world beverage sample. The methodology developed here augers well for use in other real-world samples involving saccharides as well as for sensing other desired analytes.