B. A. Dmitrieve, Y. Knirel, N. K. Kochetkov
Aug 1, 1973
Citations
0
Influential Citations
27
Citations
Journal
Carbohydrate Research
Abstract
Abstract Benzyl 2-acetamido-2-deoxy-3- O -β- D -galactopyranosyl-α- D -glucopyranoside ( 1 ) was chosen as a model bioside to develop a standard procedure for the selective cleavage of glycosidic linkages in polysaccharides containing 2-amino-2-deoxyhexose residues. Treatment of 1 with hydrazine in the presence of hydrazine sulphate resulted in quantitative N -deacetylation with the formation of benzyl 2-amino-2-deoxy-3- O -β- D -galactopyranosyl-α- D -glucopyranoside ( 2 ). The galactosyl glycosidic linkage in 2 could be selectively cleaved by acid hydrolysis. Oxidation of 2 with periodate destroyed the galactose residue. Treatment of 2 with nitrous acid cleaved the 2-amino-2-deoxy- D -glucosyl linkage to give 2,5-anhydro-3- O -β- D -galactopyranosyl- D -mannose ( 3 ) and benzyl alcohol.