Synthesis of Artificial Glycoconjugate Polymers Starting from Enzymatically Synthesized Oligosaccharides and Their Interactions with Lectins.

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Styrene derivatives substituted with N-linked β-anomeric oligosaccharides were synthesized via a simple two-step procedure starting from three enzymatically prepared oligosaccharides: N-acetyllactosamine (Galβ1-4GlcNAc), N-acetylisolactosamine (Galβ1-6GlcNAc), and 4'-galactosyllactose (Galβ1-4Galβ1-4Glc). Their homo- and copolymerization with acrylamide using 2, 2'-azobisisobutyronitrile as an initiator in dimethyl sulfoxide at 60°C gave the corresponding glycopolymers. Binding between glycopolymers and lectins was investigated by means of hemagglutination inhibition experiments. The inhibition of RCA120 lectin-induced hemagglutination by N-acetyllactosamine-carrying homopolymer was about 103 times stronger than that of the oligosaccharide itself. The enhanced binding capacity with lectins can be explained in terms of a multivalent or cluster effect along the polymeric chain. In some combinations between lectins and polymers, the copolymers inhibited hemagglutination more strongly than the homopolymers did. N-Acetyllactosamine-carrying glycopolymer showed about 3×103 times weaker inhibition of DSA lectin-induced hemagglutination than the different type of N-acetyllactosamine-carrying glycopolymer which has an O-linked β-anomeric phenyl aglycon of each repeating unit along a polyacrylamide backbone.
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