Large-scale synthesis of a Lewis B tetrasaccharide derivative, its acrylamide copolymer, and related di- and trisaccharides for use in adhesion inhibition studies with Helicobacter pylori.

The 2-aminoethyl glycoside of O-alpha-L-fucopyranosyl-(1-->2)-O-beta-D-galactopyranosyl-(1-->3)-[O-alpha-L-fucopyranosyl-(1-->4)]-2-acetamido-2-deoxy-beta-D-glucopyranose (Lewis B tetrasaccharide) was synthesized on a large scale and acryloylated with acryloyl chloride. The obtained oligosaccharide 2-acrylamidoethyl glycoside was then copolymerized with acrylamide to form a water-soluble, high molecular weight polymer, suitable for use in adhesion inhibition studies with Helicobacter pylori. Also synthesized were the corresponding derivatives of O-alpha-L-fucopyranosyl-(1-->2)-O-beta-D-galactopyranosyl-(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyranose and O-alpha-L-fucopyranosyl-(1-->2)-beta-D-galactopyranose.