The enantiomers of syn-2,3-difluoro-4-aminobutyric acid elicit opposite responses at the GABA(C) receptor

Chem Commun (Camb). 2012 Jan 21;48(6):829-31. doi: 10.1039/c1cc15816c. Epub 2011 Dec 5.

Abstract

The conformational behaviour and GABA receptor activity of the different stereoisomers of 2,3-difluoro-4-aminobutyric acid are described. Two enantiomeric GABA(C)-active ligands are identified, one of which is an agonist while the other is an antagonist. The results support an existing QSAR model of the bioactive geometry of GABA at GABA(C).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminobutyrates / chemistry*
  • Aminobutyrates / metabolism
  • Animals
  • GABA Agonists / chemistry*
  • GABA Agonists / metabolism
  • GABA Antagonists / chemistry*
  • GABA Antagonists / metabolism
  • Molecular Conformation
  • Oocytes / metabolism
  • Quantitative Structure-Activity Relationship
  • Receptors, GABA / chemistry*
  • Receptors, GABA / metabolism
  • Stereoisomerism
  • Xenopus

Substances

  • Aminobutyrates
  • GABA Agonists
  • GABA Antagonists
  • GABA-C receptor
  • Receptors, GABA