Conformational selection of non-hydrolyzable glycomimetics: the conformation of N,N′-diacetylthiochitobiose bound to wheat germ agglutinin

Abstract

The conformational behaviour of N,N′-diacetyl-4-thiochitobiose (1) has been studied using a combination of NMR spectroscopy (NOE data) and molecular mechanics calculations. Analogies and differences with the natural compound N,N′-diacetylchitobiose (2) have been found. Moreover, the study of its bound conformation to the lectin wheat germ agglutinin has also been studied using TR-NOE experiments. A process of conformational selection is observed and only one of the conformers present in aqueous solution for the free state is bound by the lectin.