Resin-bound sulfonyl azides: efficient loading and activation strategy for the preparation of theN-Acyl sulfonamide linker

Merkx, R., van Haren, M.J., Rijkers, D.T.S. and Liskamp, R.M.J. (2007) Resin-bound sulfonyl azides: efficient loading and activation strategy for the preparation of theN-Acyl sulfonamide linker. Journal of Organic Chemistry, 72(12), pp. 4574-4577. (doi: 10.1021/jo0704513)

Abstract

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.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Liskamp, Professor Robert
• Authors: Merkx, R., van Haren, M.J., Rijkers, D.T.S., and Liskamp, R.M.J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Journal of Organic Chemistry
• ISSN: 0022-3263