Highly efficient coupling of beta-substituted aminoethane sulfonyl azides with thio acids, toward a new chemical ligation reaction.
[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.
Merkx
Remco
R
Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, P.O. Box 80082, 3508 TB Utrecht, The Netherlands.
Brouwer
Arwin J
AJ
Rijkers
Dirk T S
DT
Liskamp
Rob M J
RM
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*
D001386:Azides; D010455:Peptides; D013449:Sulfonamides; D013450:Sulfones