Abstract
When the Salmonella trisaccharide epitope, methyl 3-O-(3,6-dideoxy-alpha-D-xylo-hexopyranosyl)-2-O-(alpha-D-galactopyra nos yl)- alpha-D-mannopyranoside 12 is bound by a monoclonal antibody Se155.4, the 3,6-dideoxy-alpha-D-hexose is completely buried, while the galactopyranosyl mannopyranosyl units lay across the protein surface. Crystallography of an antibody complexed with 12 also shows that the galactose residue is the most exposed saccharide. A simplified strategy to synthesize 12 and analogues modified at the galactose residue is described. Monosaccharide building blocks containing benzyl ether and ester protecting groups were used for efficient assembly of trisaccharides that can be deprotected by a single hydrogenolysis step, or occasionally preceded by a transesterification stage. Glycosylation of methyl 2-O-benzoyl-4,6-di-O-benzyl-alpha-D- mannopyranoside 4 by 2,4-di-O-benzyl-3,6-dideoxy-D-xylo-hexopyranosyl chloride 8 affords after transesterification the disaccharide acceptor 10. This disaccharide serves as a universal acceptor for glycosylation by glycosyl donors that lead, following facile deprotection, to the alpha- and beta-D-galacto, alpha- and beta-D-gluco, and 2-amino-2-deoxy-alpha-D-galacto trisaccharides 12,...Continue Reading
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