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.
Tweeddale
H J
HJ
School of Chemistry, Macquarie University, North Ryde, NSW, Australia.
Batley
M
M
Redmond
J W
JW
D001665:Binding Sites; D050260:Carbohydrate Metabolism; D002241:Carbohydrates / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry*; D006868:Hydrolysis; D017879:Isothiocyanates / Q000737:chemistry*; D007700:Kinetics; D010084:Oxidation-Reduction; D011137:Polystyrenes / Q000737:chemistry*; D013882:Thiosemicarbazones / Q000737:chemistry
D002241:Carbohydrates; D006835:Hydrazones; D017879:Isothiocyanates; D011137:Polystyrenes; D013882:Thiosemicarbazones