Toward an alternative for specific recognition of sulfated sugars. Preparation of highly specific molecular imprinted polymers

Sulfated sugars are a class of complex naturally occurring compounds some of which play central biological roles in mammals. Among them, heparan sulfates are multifunctional cell regulators, whose biological activities are related to their sulfation pattern. Determination of fine structures of these sulfated sugars is a prerequisite for understanding their biological roles. We investigated the applicability of molecular imprinting technology for recognition of the biologically relevant 6-O-sulfate substitution on sugars by using glucose-6-O-sulfate as model. Our results show that molecular imprinted polymers can specifically recognize sulfated sugars by the introduction of primary amines at the polymer side. Imprinted polymers showed excellent selectivity with regard to the sulfate position, the sugar configuration, and the presence of N-acetyl groups. These factors are essential for specific recognition of heparan sulfatesʹ sequences. Molecular imprinting technology promise a significant contribution to the selection of sulfated sugar fragments of biological relevance.