Propargyloxyproline Regio- and Stereoisomers for Click-Conjugation of Peptides: Synthesis and Application in Linear and Cyclic Peptides
Susan E. Northfield A , Simon J. Mountford A , Jerome Wielens A B , Mengjie Liu A , Lei Zhang C , Herbert Herzog C , Nicholas D. Holliday D , Martin J. Scanlon A , Michael W. Parker B E , David K. Chalmers A and Philip E. Thompson A FA Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, 381 Royal Parade, Parkville, Vic. 3052, Australia.
B ACRF Rational Drug Discovery Centre, St Vincent’s Institute of Medical Research, Fitzroy, Vic. 3065, Australia.
C Neuroscience Research Program, Garvan Institute of Medical Research, St Vincent’s Hospital, Darlinghurst, NSW 2010, Australia.
D Institute of Cell Signalling, School of Life Sciences, University of Nottingham, Queen’s Medical Centre, Nottingham NG7 2UH, UK.
E Department of Biochemistry and Molecular Biology, Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Parkville, Vic. 3010, Australia.
F Corresponding author. Email: philip.thompson@monash.edu
Australian Journal of Chemistry 68(9) 1365-1372 https://doi.org/10.1071/CH15146
Submitted: 26 March 2015 Accepted: 15 May 2015 Published: 24 June 2015
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.
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