Hj. Tweeddale et Jw. Redmond, NMR-STUDIES OF SACCHARIDE HYDRAZONES, THIOSEMICARBAZONES AND AZINES -MODEL COMPOUNDS FOR IMMOBILIZATION STUDIES, Journal of carbohydrate chemistry, 17(1), 1998, pp. 27-38
To evaluate possible chemical strategies for the solid-phase immobiliz
ation 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. Hydra
zone formation was observed to occur under milder conditions than prev
iously reported, thereby minimising the accompanying N-deacetylation w
hich occurs with N-acetamido sugars. The cyclic beta-pyranosyl structu
res of the saccharide hydrazones, thiosemicarbazones and azines were t
he preferred isomers in aqueous solution.