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

The synthesis of N-glycosyl phosphonamidates has been accomplished via the coupling of peracetylated glycosylamines with a 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.