Structural Studies of the Vibrio Cholerae O-antigen

The dominant part of the O-antigen of Vibrio cholerae is a homopolysaccharide composed of (1 leads to 2)-linked 4-amino-4,6-dideoxy-alpha-D-mannopyranosyl (perosaminyl) residues, in amino groups of which are acylated by 3-deoxy-L-glycero-tetronic acid. Most of the amino sugar is decomposed during acid hydrolysis. Treatment of the polymer with anhydrous hydrogen fluoride, which cleaves the glycosidic linkages but does not cause N-deacylation, followed by acid hydrolysis under mild conditions, produced the monomer in good yield. Treatment of the N-deacylated polysaccharide with nitrous acid caused deamination with concomitant rearrangements, typical of 4-amino-4-deoxyhexopyranosyl residues in which the amino group occupies an equatorial position.