Synthesis and Vanilloid Receptor (TRPV1) Activity of the Enantiomers of α-Fluorinated Capsaicin

Margit Winkler, Thomas Moraux, Hesham A Khairy, Roderick H Scott, Alexander MZ Slawin, David O'Hagan

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27 Citations (Scopus)

Abstract

Enantiomers of α-fluorinated capsaicin 2, have been prepared by organocatalytic electrophilic fluorination and have been used as probes for the binding conformation of capsaicin to the TRPV1 pain receptor. No enantiomeric bias is observed, thus suggesting an extended binding conformation along the molecular axis.
Original languageEnglish
Pages (from-to)823-828
Number of pages6
JournalChemBioChem
Volume10
Issue number5
Early online date6 Mar 2009
DOIs
Publication statusPublished - 23 Mar 2009

Keywords

  • capsaicin
  • fluorinated ligands
  • medicinal chemistry
  • organofluorine
  • stereoselective catalysis

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    Winkler, M., Moraux, T., Khairy, H. A., Scott, R. H., Slawin, A. MZ., & O'Hagan, D. (2009). Synthesis and Vanilloid Receptor (TRPV1) Activity of the Enantiomers of α-Fluorinated Capsaicin. ChemBioChem, 10(5), 823-828. https://doi.org/10.1002/cbic.200800709