Synfacts 2007(8): 0886-0886  
DOI: 10.1055/s-2007-968809
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

N-Acyl Sulfonamide Linker for Peptide Synthesis

Contributor(s): Yasuhiro Uozumi, Hiroe Takenaka
R. Merkx, M. J. van Haren, D. T. S. Rijkers, R. M. J. Liskamp*
Utrecht University, The Netherlands
Further Information

Publication History

Publication Date:
24 July 2007 (online)

Significance

The authors describe a novel approach to solid-phase synthesis using the N-acyl sulfonamide linker. Thus, resin-bound sulfonyl azide 1 was treated with Boc- or Fmoc-protected amino thioacids in the presence of 2,6-lutidine as a base in DMF for 3-6 hours at room temperature to give the N-acyl sulfonamide 2. The resulting N-acyl sulfonamide 2 is a convenient linker for use in Boc- or Fmoc-based solid-phase peptide synthesis to give the resin-bound N-peptidyl sulfonamide 3. Activation of the N-peptidyl sulfonamide 3 via a microwave-assisted alkylation procedure and subsequent treatment with functionalized nucleo­philes yields C-terminally modified peptides.