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N-Glycosyl phosphonamidates: potential transition-state analogue inhibitors of glycopeptidases

TitleN-Glycosyl phosphonamidates: potential transition-state analogue inhibitors of glycopeptidases
Publication TypeJournal Article
Year of Publication1998
AuthorsFerro, V, Weiler, L, Withers, SG, Ziltener, H
JournalCANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
Volume76
Pagination313-318
Date PublishedMAR
ISSN0008-4042
Abstract

The synthesis of N-glycosyl phosphonamidates has been accomplished via the coupling of peracetylated glycosylamines with an appropriate phosphonochloridate in the presence of pyridine. The resulting glycosyl phosphonamidate esters are dealkylated with bromotrimethylsilane and then deacetylated to give the target compounds, which are potential transition-state analogue inhibitors of glycopeptidases and may prove useful as haptens for generating catalytic antibodies with glycopeptidase activity.