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Dynamic Combinatorial Carbohydrate Libraries: Probing the Binding Site of the Concanavalin A Lectin
Author(s) -
Ramström Olof,
Lohmann Sophie,
Bunyapaiboonsri Taridaporn,
Lehn JeanMarie
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200305551
Subject(s) - concanavalin a , lectin , hydrazide , chemistry , linker , carbohydrate , combinatorial chemistry , biochemistry , computer science , organic chemistry , in vitro , operating system
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 μ M .