A new colorimetric boronic acid receptor for carboxy and phospho sugars

ORGN 209

Tianzhi Zhang, ztz@mail.utexas.edu and Eric V. Anslyn, anslyn@ccwf.cc.utexas.edu. Department of Chemistry and Biochemistry, University of Texas at Austin, 1 Longhorn Way, A5300, The University of Texas, Austin, TX 78712
A rigid cadmium centered tris-boronic acid receptor was synthesized, and its binding properties to various carboxy and phospho sugars were tested. This preorganized and functionalized receptor shows high affinity to different anionic sugars in aqueous solution at biological pH; especially gluconic acid, which has an association constants of ~1.0E7/M. Using an indicator displacement assay, the color change of pyrocatechol violet (PV) was observed from dark red to bright yellowish green upon addition of the guests. Taking the advantage of high gluconic acid affinity, we have applied this receptor to test the glucose level in human serum in vitro. Glucose oxidase and catalase are applied to oxidize the glucose to gluconic acid and quench the H2O2 product respectively. The generated gluconic acid is successfully detected by UV-Vis spectroscopy, from which the gluconic acid concentration is determined. Hence, the glucose level in the serum is obtained from a colorimetric determination.

 

Molecular Recognition and Self-Assembly
8:00 AM-12:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- C302, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006