Journal article
Propargyloxyproline Regio- and Stereoisomers for Click-Conjugation of Peptides: Synthesis and Application in Linear and Cyclic Peptides
SE Northfield, SJ Mountford, J Wielens, M Liu, L Zhang, H Herzog, ND Holliday, MJ Scanlon, MW Parker, DK Chalmers, PE Thompson
Australian Journal of Chemistry | Published : 2015
DOI: 10.1071/CH15146
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 broad..
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Awarded by CRC Health Group
Funding Acknowledgements
This work was supported by CRC for Biomedical Imaging Development (CRC-BID), Australia, and the Australian Research Council (ARC) Linkage project (LP0775192). This research was partly undertaken on the MX2 beamline at the Australian Synchrotron, Victoria, Australia and the authors thank the beamline staff for their assistance. Funding from the Victorian Government Operational Infrastructure Support Scheme to St Vincent's Institute is gratefully acknowledged. M.W.P. is a National Health and Medical Research Council of Australia Research Fellow. SEN and ML were supported by an Australian Post-graduate scholarship.