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

doi:10.1002/cbic.200800709

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

Medical Sciences

Research output: Contribution to journal › Article › peer-review

29 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 language	English
Pages (from-to)	823-828
Number of pages	6
Journal	ChemBioChem
Volume	10
Issue number	5
Early online date	6 Mar 2009
DOIs	https://doi.org/10.1002/cbic.200800709
Publication status	Published - 23 Mar 2009

Keywords

capsaicin
fluorinated ligands
medicinal chemistry
organofluorine
stereoselective catalysis

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10.1002/cbic.200800709

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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.",

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AU - Winkler, Margit

AU - Moraux, Thomas

AU - Khairy, Hesham A

AU - Scott, Roderick H

AU - Slawin, Alexander MZ

AU - O'Hagan, David

PY - 2009/3/23

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AB - 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.

KW - capsaicin

KW - fluorinated ligands

KW - medicinal chemistry

KW - organofluorine

KW - stereoselective catalysis

U2 - 10.1002/cbic.200800709

DO - 10.1002/cbic.200800709

M3 - Article

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JO - ChemBioChem

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ER -

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

Abstract

Keywords

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