N-Aminosulfamide Peptide Mimic Synthesis by Alkylation of Aza-sulfuryllglycinyl Peptides

N-Aminosulfamides are peptidomimetics in which the C alpha H and the carbonyl of an amino acid residue are both respectively replaced by a nitrogen atom and a sulfonyl group. Aza-sulfurylglycinyl tripeptide analogs were effectively synthesized from amino acid building blocks by condensations of N-protected amino hydrazides and p-nitrophenylsulfamidate esters. The installation of N-alkyl chains and access to other aza-sulfuryl amino acid residues were effectively achieved by chemoselective alkylation.