Resin-bound sulfonyl azides: efficient loading and activation strategy for the preparation of the N-acyl sulfonamide linker.
This paper describes an optimized protocol for the efficient loading of resin-bound aminoethane sulfonyl azides by either Boc- or Fmoc-protected amino thioacids. The resulting N-acyl sulfonamide is a convenient linker for use in Boc- or Fmoc-based solid-phase peptide synthesis. Activation of the N-acyl sulfonamide via a microwave-assisted alkylation procedure and subsequent treatment with functionalized nucleophiles yields C-terminally modified peptides that can be applied in chemoselective (bio)conjugation or ligation reactions.
Merkx
Remco
R
Department of Medicinal Chemistry and Chemical Biology, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, P. O. Box 80082, 3508 TB Utrecht, The Netherlands.
van Haren
Matthijs J
MJ
Rijkers
Dirk T S
DT
Liskamp
Rob M J
RM
D001386:Azides / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry; D012117:Resins, Synthetic / Q000737:chemistry*; D013449:Sulfonamides / Q000138:chemical synthesis*; D013450:Sulfones / Q000737:chemistry*
D001386:Azides; D003432:Cross-Linking Reagents; D012117:Resins, Synthetic; D013449:Sulfonamides; D013450:Sulfones