N-GLYCOSYL PHOSPHONAMIDATES - POTENTIAL TRANSITION-STATE ANALOG INHIBITORS OF GLYCOPEPTIDASES

The synthesis of N-glycosyl phosphonamidates has been accomplished via the coupling of peracetylated glycosylamines with an appropriate phos phonochloridate in the presence of pyridine. The resulting glycosyl ph osphonamidate esters are dealkylated with bromotrimethylsilane and the n deacetylated to give the target compounds, which are potential trans ition-state analogue inhibitors of glycopeptidases and may prove usefu l as haptens for generating catalytic antibodies with glycopeptidase a ctivity.