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Propargyloxyproline Regio- and Stereoisomers for Click-Conjugation of Peptides: Synthesis and Application in Linear and Cyclic Peptides
- Source :
- Australian Journal of Chemistry. 68:1365
- Publication Year :
- 2015
- Publisher :
- CSIRO Publishing, 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.
Details
- ISSN :
- 00049425
- Volume :
- 68
- Database :
- OpenAIRE
- Journal :
- Australian Journal of Chemistry
- Accession number :
- edsair.doi...........d904fd8467db550e338ac33d8cb83398