title: Highly efficient coupling of beta-substituted aminoethane sulfonyl azides with thio acids, toward a new chemical ligation reaction.
abstract: [reaction: see text] A highly efficient coupling of protected beta-substituted aminoethane sulfonyl azides with thio acids is reported. In the case of peptide thio acids, this method encompasses a new chemoselective ligation method. Furthermore, the resulting alpha-amino acyl sulfonamides can be alkylated with suitable electrophiles to obtain densely functionalized sulfonamide scaffolds.
authors.affiliation: Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, P.O. Box 80082, 3508 TB Utrecht, The Netherlands.
authors.forename: Remco
authors.initials: R
authors.lastname: Merkx
authors.forename: Arwin J
authors.initials: AJ
authors.lastname: Brouwer
authors.forename: Dirk T S
authors.initials: DT
authors.lastname: Rijkers
authors.forename: Rob M J
authors.initials: RM
authors.lastname: Liskamp
mesh_terms: D000478:Alkylation; D001386:Azides / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis*; D013450:Sulfones / Q000737:chemistry*
chemical_list: D001386:Azides; D010455:Peptides; D013449:Sulfonamides; D013450:Sulfones