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Selective cleavage of glycosidic linkages: studies with the model compound benzyl 2-acetamido-2-deoxy-6-O-α-D-mannopyranosyl-α-D-glucopyranoside Full article

Journal Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215
Output data Year: 1973, Volume: 30, Number: 1, Pages: 45-50 Pages count : 6 DOI: 10.1016/s0008-6215(00)82171-0
Authors Dmitrieve 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.

Abstract: N-Deacetylation of benzyl 2-acetamido-2-deoxy-6-O-α-D-mannopyranosyl-α-D-glucopyranoside (3) by alkaline hydrolysis, or hydrazinolysis in the presence of hydrazine sulphate, proceeds quantitatively to yield the amine 4. The mannosyl glycosidic linkage in 4 can be selectively hydrolysed by acid, whereas the 2-amino-2-deoxyhexosyl glycosidic linkage is selectively cleaved upon treatment with sodium nitrite in dilute acetic acid. Aspects of the selective cleavage of hexosaminoglycans are discussed.
Cite: Dmitrieve B.A. , Knirel Y.A. , Kochetkov N.K.
Selective cleavage of glycosidic linkages: studies with the model compound benzyl 2-acetamido-2-deoxy-6-O-α-D-mannopyranosyl-α-D-glucopyranoside
Carbohydrate Research. 1973. V.30. N1. P.45-50. DOI: 10.1016/s0008-6215(00)82171-0 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:A1973R381600005
Scopus: 2-s2.0-49549167921
OpenAlex: W2096199945
Citing:
DB Citing
OpenAlex 24
Web of science 21
Scopus 17
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