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Hydrazinolysis-N-reacetylation of glycopeptides and glycoproteins. Model studies using 2-acetamido-1-N-(l-aspart-4-oyl)-2-deoxy-β-d-glucopyranosylamine

✍ Scribed by Brad Bendiak; Dale A. Cumming

Publisher
Elsevier Science
Year
1985
Tongue
English
Weight
729 KB
Volume
144
Category
Article
ISSN
0008-6215

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✦ Synopsis

2-Acetamido-1-N-(L-aspart-4-oyl)-2-deoxy-beta-D-glucopyranosyla mine (1) was used as a model glycopeptide to study the hydrazinolysis-N-reacetylation procedure. The major, initial product was the beta-acetohydrazide derivative of 2-acetamido-2-deoxy-D-glucose (2) which gave 2-acetamido-2-deoxy-D-glucose (5) after exposure to acidic conditions. Very mild conditions of hydrolysis of 2 gave a 75-80% overall yield of 5 from 1 after the hydrazinolysis-N-reacetylation procedure. Several other minor compounds were detected which were not converted into 5 upon mild acid hydrolysis, indicating that 20-25% of product cannot be recovered as 5 at the reducing end of oligosaccharides.

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