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Dependence of Concanavalin A Binding on Anomeric Configuration, Linkage Type, and Ligand Multiplicity for Thiourea‐Bridged Mannopyranosyl–β‐Cyclodextrin Conjugates
Author(s) -
Baussanne Isabelle,
Benito Juan Manuel,
Ortiz Mellet Carmen,
García Fernández José Manuel,
Defaye Jacques
Publication year - 2001
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/1439-7633(20011001)2:10<777::aid-cbic777>3.0.co;2-c
Subject(s) - thiourea , chemistry , conjugate , stereochemistry , anomer , cyclodextrin , concanavalin a , ligand (biochemistry) , combinatorial chemistry , biochemistry , organic chemistry , receptor , in vitro , mathematical analysis , mathematics
No anomer discrimination: Concanavalin A (Con A) binds branched 6 I ‐( α ‐ and 6 I ‐( β ‐ D ‐mannopyranosylthioureido)cyclomaltoheptaoses with the same efficiency (see picture), in contrast with the known lectin specificity for the α anomer in the O ‐mannopyranosyl series. In addition, the presence of the cyclodextrin core slightly improves the binding efficiency. Unexpectedly, the heptakis(6‐mannopyranosylthioureido)‐β‐cyclodextrins are not recognized. Reverse (6 I →6)‐linked thioureidomannosyl ligands are only weakly bound. These results underline the influence of the spatial organization of saccharide epitopes on the functional affinity of glycoclusters.