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Propargyloxyproline Regio- and Stereoisomers for Click-Conjugation of Peptides: Synthesis and Application in Linear and Cyclic Peptides


The use of the click reaction for the introduction of conjugate groups, such as affinity or fluorescent labels, to a peptide for the study of peptide biochemistry and pharmacology is widespread. However, the nature and location of substituted 1,2,3-triazoles in peptide sequences may markedly affect conformation or binding as compared with native sequences. We have examined the preparation and application of propargyloxyproline (Pop) residues as a precursor to such peptide conjugates. Pop residues are available in a range of regio- and stereoisomers from hydroxyproline precursors and are readily prepared in Fmoc-protected form. They can be incorporated routinely in peptide synthesis and broadly retain the conformational properties of the parent proline containing peptides. This is exemplified by the preparation of biotin- and fluorophore-labelled peptides derived from linear and cyclic peptides.

Type Journal
ISBN 0004-9425
Authors Northfield, S. E. ; Mountford, S. J. ; Wielens, J. ; Liu, M. J. ; Zhang, L. ; Herzog, H. ; Holliday, N. D. ; Scanlon, M. J. ; Parker, M. W. ; Chalmers, D. K. ; Thompson, P. E.;
Published Date 2015-01-01
Published Volume 68
Published Issue 9
Published Pages 1365-1372
Status Published in-print
URL link to publisher's version <Go to ISI>://WOS:000360990400008