Synthesis of methyl alpha-glycosides of some higher oligosaccharide fragments of the O-antigen of Vibrio cholerae O1, serotype Inaba and Ogawa.
The title oligosaccharides, the tri- through the hexasaccharide in the Inaba series and the penta- and the hexasaccharide in the Ogawa series, have been synthesized using 1-thioglycosides of precursors to 3-O-benzyl-perosamine (4-amino-4,6-dideoxy-D-mannose) as building blocks and N-iodosuccinimide/silver triflate as a promoter. The azido groups in the assembled oligosaccharides were reduced to amino groups, which were then acylated using 2,4-O-benzylidene-3-deoxy-L-glycero-tetronic acid as the derivatizing reagent. Catalytic hydrogenolysis, simultaneously of the benzyl and benzylidene groups, gave the desired products that were characterized by 1H and 13C NMR spectroscopy.
Zhang
J
J
NIDDK, National Institutes of Health, Bethesda, MD 20892-0815, USA.
Kovác
P
P
D000215:Acylation; D001593:Benzyl Compounds; D001597:Benzylidene Compounds; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D008745:Methylation; D015394:Molecular Structure; D019081:O Antigens / Q000737:chemistry*; D009844:Oligosaccharides / Q000737:chemistry*; D013388:Succinimides; D013438:Sulfhydryl Compounds; D014734:Vibrio cholerae / Q000737:chemistry / Q000276:immunology*
D001593:Benzyl Compounds; D001597:Benzylidene Compounds; D006027:Glycosides; D019081:O Antigens; D009844:Oligosaccharides; D013388:Succinimides; D013438:Sulfhydryl Compounds; C008155:N-iodosuccinimide