SYNTHESIS OF C-GLYCOPEPTIDES VIA FREE-RADICAL ADDITION OF GLYCOSYL BROMIDES TO DEHYDROALANINE DERIVATIVES

In only one reaction step, nonnatural C-glycopeptides of type 1 can be obtained (see right, (S) form). This new class of molecules has remarkable properties; their high chemical stability recommends them as potential glycosidase inhibitors. The absolute configuration of the C-glycopeptides can be elucidated with NMR spectroscopy and molecular dynamics calculations. (R1,R2 = H, OAc, sugar; R3,R4 = protecting group).