title: N-Aminosulfamide peptide mimic synthesis by alkylation of aza-sulfurylglycinyl peptides.
abstract: N-Aminosulfamides are peptidomimetics in which the C(α)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.
authors.affiliation: Département de chimie, Université de Montréal, C.P. 6128, Succursale Centre-Ville, Montréal, Québec H3C 3J7, Canada.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Turcotte
authors.forename: Samir H
authors.initials: SH
authors.lastname: Bouayad-Gervais
authors.forename: William D
authors.initials: WD
authors.lastname: Lubell
mesh_terms: D000478:Alkylation; D000577:Amides / Q000737:chemistry*; D000586:Amination; D001372:Aza Compounds / Q000737:chemistry*; D040761:Biomimetic Materials / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis*; D013457:Sulfur Compounds / Q000737:chemistry*
chemical_list: D000577:Amides; D001372:Aza Compounds; D010455:Peptides; D013457:Sulfur Compounds