Design and synthesis of boronic acid-based sensors for cell surface carbohydrate recognition

CARB 76

Gurpreet Kaur, wang@gsu.edu, Senol Akay, sakay@student.gsu.edu, and Binghe Wang, wang@gsu.edu. Department of Chemistry, Georgia State University, Atlanta, GA 30303
Cell surface carbohydrate signatures quite often are biomarkers for different types of cells and pathological states. Small molecule lectin mimics that can recognize such signature carbohydrates can be used for the development of diagnostics, imaging, and therapeutic agents. Along this line, we are interested in developing fluorescent boronolectins for Lewis X. Based on the reversible and tight complexation between the boronic acid moiety and diols as well as our own discovery of several boronic acid reporters that change fluorescent properties upon sugar binding, we have designed a series of potential Lewis X sensors (fluorescent boronolectins) that rely on a two-point recognition which includes boronic acid-diol and anionic interactions. This presentation will give a detailed description of the computer-aided design of such sensors, their synthesis, and binding evaluation.