Selective cleavage of glycosidic linkages

Selective cleavage of glycosidic linkages Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 1973, Volume: 29, Number: 2, Pages: 451-457 Pages count : 7 DOI: 10.1016/s0008-6215(00)83031-1

Authors

Dmitriev B.A. ¹ , Knirel Yu.A. ¹ , Kochetkov N.K. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of U.S.S.R. Moscow U.S.S.R.

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.

Dmitriev B.A. , Knirel Y.A. , Kochetkov N.K.
Selective cleavage of glycosidic linkages
Carbohydrate Research. 1973. V.29. N2. P.451-457. DOI: 10.1016/s0008-6215(00)83031-1 WOS Scopus OpenAlex

Web of science:	WOS:A1973R222300018
Scopus:	2-s2.0-15644366032
OpenAlex:	W4247585738

DB	Citing
OpenAlex	56
Web of science	55
Scopus	54