Binding of carbohydrates to solid supports, Part 2: Reaction of sugar hydrazones with isothiocyanate-substituted polystyrene.

The binding of sugars to a polymer support as thiosemicarbazones has been investigated as a means of immobilizing glycans. Hydrazones of glucose and N-acetylglucosamine were prepared by reaction with hydrazine hydrate, and successfully reacted with isothiocyanate-substituted polystyrene by incubation at room temperature and neutral pH. The binding was efficient and stable in aqueous buffers over a range of pH conditions. The bound sugars were recovered in moderate yield by treatment of the beads with hydrazine hydrate, benzaldehyde or acetone. Direct binding of reducing sugars to thiosemicarbazide-substituted polystyrene was not successful because of the unfavourable thermodynamics.