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

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