NMR Studies of Saccharide Hydrazones, Thiosemicarbazones and Azines: Model Compounds for Immobilisation Studies

Abstract

Abstract To evaluate possible chemical strategies for the solid-phase immobilization of sugars, studies on the formation and stability of hydrazones, thiosemicarbazones and azines of D-glucose and 2-acetamido-2-deoxy-D-glucose, and the subsequent release of sugars, were carried out. Hydrazone formation was observed to occur under milder conditions than previously reported, thereby minimising the accompanying N-deacetylation which occurs with N-acetamido sugars. The cyclic β-pyranosyl structures of the saccharide hydrazones, thiosemicarbazones and azines were the preferred isomers in aqueous solution.