Molecular Design of Glycopolymers Having Biological Recongnition Function via Glycosidation

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The hemagglutinin glycoprotein (HA) of the influenza virus membrane is responsible for binding the cell surface receptors during infection, ant sialyllactose is known to bind to the influenza HA.We synthesized sialyllactose-carrying glycopolymers via a convenient procedure using a mixture of alpha(2-3) and alpha(2-6)-linked isomeric sialyllactose (the molar ratio, 6.5 : 1) isolated from bovine milk. The interaction of sialyllactose-carrying glycopolymers with virus was investigated by means of inhibition of hemagglutination. These glycoconjugate polymers inhibited hemagglutinating activity of virus more strongly than the corresponding sugar itself. The inhibition with sialyllactose-carrying homopolymer was about 1*10^3 times that with silalyllactose.A convenient one-step synthetic method is proposed to prepare stirene derivatives substituted with sialomono- and sialodisaccharides. N-Acetylneuraminic acid (Neu5Ac) and sialodisaccharide (Neu5Acalpha2-8Neu5Ac) were treated with p-vinylbenzylamine in the presence of amidation reagents and the resulting stirene derivatives were homo- and copolymerized with acrylamide in the presence of redox initiator. The polymers interacted with WGA lecting more strongly than the corresponding monomer. Mol fraction of sugars in polymer had influence on the recognition of WGA lectin. THe strongest binding was observed for the copolymer bearing sialomonosaccharide (mol fraction of sugar in copolymer : 0.32). The copolymer bearing sialomonosaccharide (mol fraction of sugar in copolymer : 0.13) showed hemagglutinating activity at 0.02mM concentration..