Synthesis of Biocompatible Materials Having Blood-Group Antigenic 01 igosaccharide Chain

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A new polymerizable monomer having a nonreducing-terminal trisaccharide of an H type antigenic oligosaccharide was synthesized chemically, that is, 5-(2-acryloyloxyethylaminocarbonyl)pentyl 2-acetamido-4,6-0-benzylidene-2-deoxy-3-0-[3,4,6-tri-0-benzyl-2-0-(2,3,4- tri-0-benzyl-alpha-L-fucopyranosyl)-beta-D-galactopyranosyl]-beta-D-glucopyranoside, and was copolymerized with acrylamide or methyl acrylate. Copolymerization of the synthetic sugar monomer with acrylamide was carried out in dimethylformamide with AIBN as initiator, and copolymerization with methyl acrylate was carried out in benzene with the same initiator. The copolymer composition which was calculated by ^1H-NMR spectroscopy was controlled by the monomer ratio in the feed. The monomeric unit having an H type antigenic oligosaccharide was introduced into the copolymer in a content of 0.005 to 0.54. The number average molecular weight of the copolymer was in the range of 1.8 X 10^4 to 8.4 X 10^4. Benzyl and benzylidene groups, which were the protective groups of the copolymers, were removed by catalytic hydrogenation over palladium-carbon in the mixed solvent of DMF-H_2O. Transfer of N-acetyl-D-galactosamine to the galactose residue in the copolymer by using A enzyme (GalNAc transferase) was attempted, showing the transfer of GalNAc residue.