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-α-L-fucopyranosyl-(1→2)-O-β-D-galactopyranosyl-(1→3)-[O-α-L-fucopyranosyl-(1→4)]-2-acetamido-2-deoxy-β-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-α-L-fucopyranosyl-(1→2)-O-β-D-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranose and O-β-L-fucopyranosyl-(1→2)-β-D-galactopyranose. Present adress: Astra Production Chemicals, S-151 85 Sodertalje, Sweden. Present adress: Pharmacia Biotech AB, Bjorkgatan 30, S-751 82, Uppsala, Sweden.