Selective cleavage of glycosidic linkages: studies with the O-specific polysaccharide from Shigella dysenteriae type 3

Carbohydr Res. 1975 Apr;40(02):365-72. doi: 10.1016/s0008-6215(00)82617-8.

Abstract

Treatment of the O-specific polysaccharide from Shigella dysenteriae Type 3 with hydrazine in the presence of hydrazine sulphate resulted in quantitative N-deacetylation with the formation of a modified polysaccharide containing free amino groups. Oxidation of the modified polysaccharide with periodate did not destroy the 2-amino-2-deoxygalactose residues, thus indicating that they were substituted at position 3. Acid hydrolysis of the modified polysaccharide afforded 3-O-(2-amino-2-deoxy-beta-D-galactopyranosyl)-D-galactose, which was identified as the N-acetyl derivative. Deamination of the modified polysaccharide with nitrous acid cleaved the 2-amino-2-deoxy-D-galactopyranosyl linkages to give a pentasaccharide as the major product, which appeared to be the modified chemical repeating unit of the O-specific polysaccharide.

MeSH terms

  • Acetylation
  • Antigens, Bacterial / analysis*
  • Deamination
  • Hydrolysis
  • Methylation
  • Molecular Conformation
  • Oxidation-Reduction
  • Polysaccharides, Bacterial / analysis
  • Shigella dysenteriae / analysis*

Substances

  • Antigens, Bacterial
  • Polysaccharides, Bacterial