Synthesis of spaced trisaccharides with blood group A and B specificity, their fragments, and structural analogs

Trisaccharides GalNAc alpha 1---3(Fuc alpha 1---2)Gal and Gal alpha 1---3(Fuc alpha 1---2)Gal, which are the determinant fragments of the human blood group specific antigens A and B, respectively, were synthesized as R-glycosides (R = beta-OCH2CH2CH2NHCOCF3). 4,6-BdGal-R was acetylated selectively a...

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Bibliographic Details
Published inBioorganicheskaia khimiia Vol. 18; no. 2; p. 283
Main Authors Korchagina, E Iu, Bovina, N V
Format Journal Article
LanguageRussian
Published Russia (Federation) 01.02.1992
Subjects
ABO Blood-Group System - metabolism
Carbohydrate Sequence
Humans
Molecular Sequence Data
Substrate Specificity
Trisaccharides - chemical synthesis
Trisaccharides - metabolism
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Summary:Trisaccharides GalNAc alpha 1---3(Fuc alpha 1---2)Gal and Gal alpha 1---3(Fuc alpha 1---2)Gal, which are the determinant fragments of the human blood group specific antigens A and B, respectively, were synthesized as R-glycosides (R = beta-OCH2CH2CH2NHCOCF3). 4,6-BdGal-R was acetylated selectively at 3-OH, the 3-O-acetate was alpha-fucosylated and then deacetylated to give a protected H-disaccharide bearing a free 3-OH. The disaccharide was alpha-glycosylated with 2-azido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-galactopyranosyl chloride (GCl) or 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl bromide (GBr) to give protected spacered trisaccharides A and B, respectively. Disaccharides GalNAc alpha 1---3Gal-R and Gal alpha 1---3Gal-R were synthesized in two ways. 1. Hydrogenolysis followed by benzylidenation of Bzl3-2-O-Ac-Gal-R gave 4,6-Bd-2-O-Ac-Gal-R, which was alpha-glycosylated with GCl and GBr. 2. The required disaccharides were isolated from the mixture of di- and trisaccharides which was obtained by selective glycosylation of 4,6-Bd-Gal-R with GCl and GBr. Synthesis of GalNAc alpha 1---3(GalNAc alpha 1---2)Gal and Gal alpha 1---3(Gal alpha 1---2)Gal, non-natural analogues of A and B trisaccharides, is also described. Deprotected R-glycosides were converted to OCH2CH2CH2NH2 (R1) derivatives, N-biotinyl derivatives were synthesized from GalNAc alpha 1---3(Fuc alpha 1---2)Gal-R1 and Gal alpha 1---3(Fuc alpha 1---2)Gal-R1 glycosides. The oligosaccharides, their macromolecular forms, and affinity sorbents obtained from them were used in the epitope specificity studies of the monoclonal antibodies and blood group typing.
ISSN:0132-3423