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Immunochemical studies on blood groups. 38. Structures and activities of oligosaccharides produced by alkaline degradation of blood-group Lewis-a substance. Proposed structure of the carbohydrate chains of human blood-group A, B, H, Le-a, and Le-b substances



Immunochemical studies on blood groups. 38. Structures and activities of oligosaccharides produced by alkaline degradation of blood-group Lewis-a substance. Proposed structure of the carbohydrate chains of human blood-group A, B, H, Le-a, and Le-b substances



Biochemistry 7(8): 2976-2990



Treatment of blood-group Lea substance with NaOD-NaBD4 gave reduced oligosaccharides by peeling of the carbohydrate chains from their reducing ends after they had been released from the protein portion by alkaline elimination. Three reduced monosaccharides were identified: 3-hexenetetrol, galactitol, and 2-acetamido-2-deoxy-D-galactitol. Two reduced disac-charides containing D-galactose and either 2-acetamido-2-deoxy-D-glucitol or 2-acetamido-2-deoxy-D-galactitol were partially characterized. One trisaccharide, [beta]-D-Gal(1[forward arrow]4)-[beta]-D-GNAc-(1[forward arrow]6?)-3-hexenetetrol, was isolated from the alkaline degradation of other blood group substances while the other, [beta]-D-Gal-(1[forward arrow]4)-[beta]-D-GNAc-(1[forward arrow]6)-hexane-l,2,4,5,6-pentol, contains a reduced residue not previously identified. Only 2 monofucosyl oligosaccharides were isolated: [beta]-D-Gal-(1[forward arrow]3)-[[alpha]-L-Fuc-(1[forward arrow]4)]-[beta]-D-GNAc-(1[forward arrow]3 or 4)-D-galactitol (I) and [beta]-D-Gal-(1[forward arrow]4)[[alpha]-L-Fuc-(1[forward arrow]3)]-[beta]-D-GNAc-(1[forward arrow]6?)-[beta]-hexenetetrol (II); these 2 oligosaccharides have type 1 and type 2 chains, respectively. Their structures were determined by analysis, methylation, partial acid hydrolysis, and periodate oxidation studies. Oligosaccharide I was highly Lea active in inhibition of hemagglutination and precipitation whereas II had very little inhibitory activity; this difference in the activities of the 2 types of determinants is in contrast to the A and H oligosaccharides previously isolated in which both chains have approximately equal activities. A reduced tetrasaccharide, [beta]-D-Gal-(1[forward arrow]3 or 4)-[beta]-D-GNAc-(1[forward arrow]6)-[beta]-D-Gal-(1[forward arrow]3)]-2-acetamido-2-deoxy-D- galactitol, is thought to be derived from the linkage region. In the original blood-group substance the chains would be linked through the 2-acet-amido-2-deoxy-D-galactose of this structure to serine and threonine in the polypeptide portion. A branched oligosaccharide, [beta]-D-Gal-(1[forward arrow]3)-[beta]-D-GNAc-[beta]-D-Gal-(1[forward arrow]4)-D-GNAc]-D-galactitoi, was isolated; it is of particular significance since it contains both type 1 and type 2 chains linked to the same galactitol residue. The branching in this oligosaccharide was established by demonstrating the tetra-O-methyl-D-galactose was the only galactose methyl ether occurring after methylation and hydrolysis and by showing that both D-galactosyl residues could be removed by [beta]-galactosidase. The structure of this oligosaccharide accounts for many features of the alkaline degradation of blood-group substances. Based on this key structure, the oligosaccharides previously isolated from blood-group substances may be assembled into a megalosaccharide representing the structure of the majority of the carbohydrate chains found in blood-group A, B, H, Lea, and Leb substances.

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Accession: 068620112

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PMID: 5691821

DOI: 10.1021/bi00848a039


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