Biomacromolecules, Vol.1, No.1, 68-74, 2000
A facile synthetic approach to L- and P-selectin blockers via copolymerization of vinyl monomers constructing the key carbohydrate modules of sialyl Lewis(x) mimics
A highly practical synthetic approach is described for artificial L-and P-selectin blockers. The synthesis involves radical bi- and terpolymerizations of p-(N-acrylamido)phenyl 3- or/and 6-sulfo-beta -D-galactoside with allyl alpha -L-fucoside in the presence of acrylamide, Each of the two glycosyl monomers constructs a key carbohydrate module responsible for selectins/sulfated sialyl Lewis(X) (sLe(X)) bindings. Whereas an acrylamide copolymer carrying 3-sulfo-galactoside showed no activity for any selectins, the fucosylated terpolymer showed a potent activity to block both of P- and L-selectins/sLe(X) binding at a concentration of a few micrograms per milliliter. The enhanced activity is apparently ascribed to the cooperative binding effects of the fucoside and the 3-sulfo-galactoside residues.