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

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.

authors

  • Northfield, Susan E
  • Mountford, Simon J
  • Wielens, Jerome
  • Liu, Mengjie
  • Zhang, Lei
  • Herzog, Herbert
  • Holliday, Nicholas D
  • Scanlon, Martin J
  • Parker, Michael W
  • Chalmers, David K
  • Thompson, Philip E

publication date

  • 2015