Synthesis and structural studies of asparagine-modified 2-deoxy-alpha-N-glycopeptides associated with the renin-angiotensin system.

Following addition of N-iodosuccinimide to glycals, reductive hydrogenolysis and ring opening gave 2-deoxy-alpha-N-glycopeptides carrying a deaminated asparagine unit. This reaction could be performed employing glucal, galactal, L-rhamnal, L-fucal and lactal to give the corresponding glycoconjugate building blocks 11, 12, 17, 22, 27 and 32. Further NIS-mediated glycosylation of the rhamno derivative 21 led to simple trisaccharide peptide adducts 45. Peptide synthesis of the gluco building unit with different preassembled oligopeptides afforded glycoconjugates 36, 39, 41 and 42 assumed to be of interest as potential inhibitors of the renin-angiotensin system.