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

• Published in: Chembiochem : a European journal of chemical biology Vol. 10; no. 5; pp. 823 - 828
• Main Authors: Winkler, Margit, Moraux, Thomas, Khairy, Hesham A., Scott, Roderick H., Slawin, Alexandra M. Z., O'Hagan, David
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 23.03.2009; WILEY‐VCH Verlag
• Subjects: Animals; capsaicin; Capsaicin - chemical synthesis; Capsaicin - metabolism; fluorinated ligands; Fluorine Compounds - chemical synthesis; Fluorine Compounds - metabolism; Ganglia, Spinal - cytology; Halogenation; Humans; medicinal chemistry; Molecular Conformation; Molecular Structure; Neurons - cytology; Neurons - physiology; organofluorine; Rats; Rats, Sprague-Dawley; Stereoisomerism; stereoselective catalysis; TRPV Cation Channels - metabolism
• ISSN: 1439-4227; 1439-7633; 1439-7633
• DOI: 10.1002/cbic.200800709

Spicing it up with fluorine: 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. Spicing it up with fluorine: 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.