Aspinall GO, Gammon DW, Sood RK, Chatterjee D, Rivoire B, Brennan PJ Structures of the glycopeptidolipid antigens of serovars 25 and 26 of the Mycobacterium avium serocomplex, synthesis of allyl glycosides of the outer disaccharide units and serology of the derived neoglycoproteins Carbohydrate Research237 (1992)
57-77
The structure was elucidated in this paper Publication DOI:10.1016/S0008-6215(92)84233-I Journal NLM ID:0043535 Publisher: Elsevier Institutions: Department of Chemistry, York University, North York, Toronto, Ontario M3J 1P3, Canada
The pentasaccharide hapten released from the glycopeptidolipid (GPL) antigen of M. auium serovar26 has been characterized as O-(2,4-di-O-methyl-α-l-fucopyranosyl)-(1 → 4)-O-β-d-gluco-pyranosyluronic acid-(1 → 4)-O-(2-O-methyl-α-l-fucopyranosyl)-(1 → 3)-α-l-rhamnopyranosyl-(1 #x02192; 2)-6-deoxy-l-talose. The allyl glycosides of the outer glycosyl and glycobiosyl units of this hapten have been synthesized, the latter by a route involving oxidation of the corresponding d-glucopyranose derivative. Conjugation of allyl glycosides to protein by ozonolysis and reductive coupling afforded neoantigens (neo 26−1 and 26−2), both of which interacted with antibodies to M. avium serovar 26. The terminal sugar residue of the pentasaccharide hapten of the serovar 25 GPL had been shown to have the galacto configuration on the basis of 1H-13C NMR correlation spectroscopy, but absolute configurational assignment for the sugar awaited the synthesis, as for neo 26, of two glycobiosyl NGPs bearing the terminal sugar in the d and l enantiomeric forms, respectively. Only the glycobiosyl NGP bearing the terminal sugar as the d-enantiomer interacted with antibodies to M. avium serovar 25, thus providing evidence for the absolute configuration of the sugar, and showing that the complete oligosaccharide hapten has the structure, O-(4-acetamido-4,6-dideoxy-2-O-methyl-α-d-galactopyranosyl)-(1 → 4)-O-β-d-glucopyranosyluronic acid-(1 → 4)-O-(2-O-methyl-α-l-fucopyranosyl)-(1 → 3)-O-α-l-rhamnopyranosyl-(1 → 2)-6-deoxy-l-talose.
Found 
report error
