Chemoselective coupling of peptide fragments using the Staudinger ligation

Merkx, R., Rijkers, D.T.S., Kemmink, J. and Liskamp, R.M.J. (2003) Chemoselective coupling of peptide fragments using the Staudinger ligation. Tetrahedron Letters, 44(24), pp. 4515-4518. (doi: 10.1016/S0040-4039(03)01014-1)

Abstract

Here we report the first Staudinger ligations which yield tetra- and pentapeptides starting from N-terminal α-azido peptides and C-terminal peptideo-(diphenylphosphine)phenyl esters. Mass spectrometric analysis of the reaction mixture provided a better insight into the mechanism of the Staudinger ligation and has been used to explain the observed intermediates and to optimize the ligation reaction. As a result, the optimized reaction enables the chemoselective coupling of peptides containing amino acids other than glycine at the ligation site.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Liskamp, Professor Robert
• Authors: Merkx, R., Rijkers, D.T.S., Kemmink, J., and Liskamp, R.M.J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Tetrahedron Letters
• ISSN: 0040-4039