Synthesis of glycoconjugate polymer carrying globotriaose as artificial multivalent ligand for Shiga toxin-producing Escherichia coli O157:H7

As an artificial ligand, a glycoconjugate, polymer carrying carbohydrate moiety of lactosyl ceramide or globotriaosyl ceramide (Gb(3)) was synthesized. Gb(3) is known as the receptor of Shiga toxin-producing Escherichia coli O157:H7. The preparation of the glycoconjugate, polymer initially involves the construction of the carbohydrate moiety of Gb(3) derivative which has n-pentenyl group as polymerizable group. In addition, the n-pentenyl group of the Gb(3) derivative was modified and different polymerizable groups such as acrylamide group were introduced at omega-position of the aglycon. Radical polymerization of the synthesized glycosyl monomers with or without acrylamide proceeded smoothly in water using ammonium persulfate and N, N, N', N'-tetramethylethylenediamine as usual initiator system and gave water-soluble glycoconjugate polymers having various polymer compositions. These polymers have the potential to neutralize Shiga toxin by reason of cluster effect and multivalency. (C) 2004 Elsevier Ltd. All rights reserved.