SUGAR BINDING POLYMERS SHOWING HIGH ANOMERIC AND EPIMERIC DISCRIMINATION OBTAINED BY NONCOVALENT MOLECULAR IMPRINTING

Noncovalent molecular imprinting of sugar compounds in ethylene glycol dimethacrylate-methacrylic acid copolymers yielded materials containi ng highly selective sugar binding sites. Investigation of a range of p olymers demonstrated that the resulting polymer imprints have a high d egree of both anomeric and epimeric selectivity favoring the original print molecule. In HPLC assays, a polymer imprinted using p-nitropheny l-beta-D-galactoside could separate the alpha and beta anomers of the same compound with near baseline resolution. A polymer imprinted using p-nitrophenyl-beta-D-galactoside showed similar results but with the beta anomers retained longer as expected. Anomeric discrimination of c losely related sugars was also possible, with the degree of separation depending on the structural resemblance to the print molecule. Simila rly, a polymer imprinted with p-nitrophenyl-alpha-L-fucoside could sep arate alpha/beta mixtures of p-nitrophenyl-L-fucoside with baseline re solution. Using radioligand displacement assays a polymer imprinted us ing octyl-alpha-D-glucoside was shown to bind methyl-alpha-D-glucoside with a 40-fold higher affinity than that for the beta-anomer. The epi meric selectivity was even more impressive: methyl-alpha-D-mannoside a nd methyl-alpha-D-galactoside had 130- and 240-fold lower affinity, re spectively, than methyl-alpha-D-glucoside. The results are discussed i n relation to possible uses of such polymers in separation and analysi s. (C) 1994 Academic Press, Inc.