Propargyloxyproline regio- and stereoisomers for click-conjugation of peptides: synthesis and application in linear and cyclic peptides

Susan Ellen Northfield, Simon John Mountford, Jerome Wielens, Mengjie Liu, Lei Zhang, Herbert Herzog, Nicholas D Holliday, Martin Scanlon, Michael William Parker, David Kenneth Chalmers, Philip Thompson

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8 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)1365-1372
Number of pages8
JournalAustralian Journal of Chemistry
Volume68
Issue number9
DOIs
Publication statusPublished - 2015

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