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Synthesis, conformation and biological evaluation of the enantiomers of 3-fluoro-gamma-aminobutyric acid ((R)- and (S)-3F-GABA): An analogue of the neurotransmitter GABA

Author(s): G. Deniau, A. M. Z. Slawin, T. Lebl, F. Chorki, J. P. Issberner, T. van Mourik, J. M. Heygate, J. J. Lambert, L. A. Etherington, K. T. Sillar, D. O'Hagan

gamma-Aminobutyric acid or GABA (1) is one of the major inhibitory amino acid neuro transmitters of the central nervous system. This article describes the first synthesis of both the (R)- and (S)- enontiomers of 3-fluoro-GABA (2, 3F-GABA). DFT calculations were carried out in a continuum solvent model (PCM-B3LYP) to estimate the preferred conformations of 3F-GABA in aqueous solution. NMR coupling constants were calculated for each conformer and were then used to simulate the NMR spectra to evaluate the solution conformation of 3F-GABA. A preliminary evaluation of the 3F-GABA enantiomers shows that they act similarly as agonists of cloned GABAA receptors; however, they behave quite differently in a whole animal (Xenopus laevis tadpole model).

Full version: Available here

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ISBN: 1439-4227
Publication Year: 2007
Periodical: Chembiochem
Periodical Number: 18
Volume: 8
Pages: 2265-2274
Author Address: