Synthesis of a new polymer containing a blood-group antigenic oligosaccharide chain

Abstract

A new polymerizable monomer having a nonreducing-terminal trisaccharide of an H type antigenic oligosaccharide was synthesized chemically, that is, 5- [[ [2-(acryloyloxy)ethyl]amino]carbonyl]-pentyl2-(acetoamido)-4,6-0-benzylidene-2-deoxy-3-0-[3,4,6-tri-0-benzyl-2-0-(2,3,4-tri-0-benzyl-a-L-fucopyranosyl)-/3-D-galactopyranosyl]-0-D-glucopyranoside (3), and was copolymerized with acrylamide or methyl acrylate. Copolymerization of 3 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 *H NMR spectroscopy was controlled by the monomer ratio in the feed. 3 was introduced into the copolymer in a content of 0.005-0.54. The number-average molecular weight of the copolymer was in the range of (1.8-8.4) x 104. Benzyl and benzylidene groups, which were the protective groups of the copolymers, were completely removed by catalytic hydrogenation over palladium-carbon in the mixed solvent.

Glycosyl Transfer Reaction to the Oligosaccharide Chain on the Synthetic Polymer

“…-/J-o-glucopyranoside and acrylamide was carried out in DMF with AIBN as catalyst at 70°C under high vacuum, and the obtained copolymer was deprotected as described previously. 3 The structure of deprotected copolymer is shown in Figure 1 radioactivity in a liquid scintillation spectrometer.…”

“…2 In the previous work, we synthesized a novel polymeric material having chemically synthesized H type oligosaccharide by copolymerization of oligosaccharide-containing monomer with acrylamide. 3 In this investigation, transfer of N-acetyl-o-galactosamine to the galactose residue of Hl type oligosaccharide on the synthetic copolymer was attempted.…”