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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.;
Garvan Authors Prof Herbert Herzog
Publisher Name AUST J CHEM
Published Date 2015-01-01 00:00:00
Published Volume 68
Published Issue 9
Published Pages 1365-1372
URL <Go to ISI>://WOS:000360990400008
Status Published In-print