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.
- fluorinated ligands
- medicinal chemistry
- stereoselective catalysis
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