Synthesis of blood group oligosaccharides with A, B and H (type 3) specificity
T. V. Zemlyanukhina, N. V. Bovin
M. M. Shemyakin Institute of Bioorganic Chemistry, Academy of Sciences of the USSR, Moscow
Abstract: Chemical synthesis of A, B, and H (type 3) human blood group determinant oli-gosaccharides (as R-glycosides, R=OCH2CH2CH2NHCOCF3) and their polymeric derivatives are reported. 4,6; 4',6'-Di-O-benzylidene derivative of Galβ1→3SGalNAcα1→R was chloroacetylated selectively at 3'-OH, the chloroacetate was α-fucosylated and dechloroacetylated to give protected H (type 3) trisaccharide bearing free 3'-OH. α-Gly-cosylation of the trisaccharide with 2-azido-3,4,6-tri-O-benzyl-β-D-galactopyranosyl chloride and 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl bromide gave rise to protected A and B tetrasaccharides, respectively.
Deprotected R-glycosides were converted to OCH2CH2CH2NH2 derivatives. Their reaction with poly(4-nitrophenylacrylate) affords polyacrylamide-coupled conjugates with A, B, and H (type 3) specificity.
Russian Journal of Bioorganic Chemistry 1990, 16 (8):1096-1104