Dynamic Combinatorial Carbohydrate Libraries: Probing the Binding Site of the Concanavalin A Lectin

✍ Scribed by Olof Ramström; Sophie Lohmann; Taridaporn Bunyapaiboonsri; Jean-Marie Lehn

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 123 KB
• Volume: 10
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200305551

✦ Synopsis

Abstract

Dynamic combinatorial chemistry (DCC) has emerged as an efficient approach to receptor/ligand identification based on the generation of combinatorial libraries by reversible interconversion of the library constituents. In this study, the implementation of such libraries on carbohydrate–lectin interactions was examined with the plant lectin Concanavalin A as a target species. Dynamic carbohydrate libraries were generated from a pool of carbohydrate aldehydes and hydrazide linker/scaffold components through reversible acylhydrazone exchange, resulting in libraries containing up to 474 constituents. Dynamic deconvolution allowed the efficient identification of the structural features required for binding to Concanavalin A and the selection of a strong binder, a tritopic mannoside, showing an IC~50~‐value of 22 μM.