111
Views
1
CrossRef citations to date
0
Altmetric
Review

3-Fluoro-GABA Enantiomers: Exploring the Conformation of GABA Binding to GABAA Receptors and GABA Aminotransferase

Pages 189-195 | Published online: 11 Feb 2011

Bibliography

  • Murray CW , ReesDC. The rise of fragment-based drug discovery.Nature Chem.1, 187–192 (2009).
  • Deniau G , SlawinAM, LeblTet al. Synthesis, conformation and biological evaluation of the enantiomers of 3-fluoro γ-aminobutyric acid ((R)- and (S)- 3F-GABA). An analogue of the neurotransmitter, GABA. ChemBioChem 8, 2265–2274 (2007).
  • Clift DC , HaitaoJ, DeniauGP, O‘HaganD, SilvermanRB. Enantiomers of 4-amino-3-fluorobutanoic acid as substrates for g-aminobutyric acid aminotransferase. Conformational probes for GABA binding.Biochemistry46, 13819–13828 (2007).
  • Chebib M , JohnstonGA. GABA-activated ligand gated ion channels: medicinal chemistry and molecular biology.J. Med. Chem.43, 1427–1447 (2000).
  • Clayton T , ChenJL, ErnstMet al. An updated unified pharmacophore model of the benzodiazepine binding site on GABAA receptors: correlation with comparative models. Curr. Med. Chem. 14, 2755–2775 (2007).
  • Schwenk J , MetzM, ZollesGet al. Native GABAB receptors are hereomultimers with a family of auxiliary subunits. Nature 465, 231–237 (2010).
  • Abdel-Halim H , HanrahanJR, HibbsDE, JohnsonGAR, ChebibM. A molecular basis for the agonist and antagonist actions at GABAC receptors. Chem. Biol. Drug. Des.71, 306–327 (2008).
  • Allan RD , FongJ. Synthesis of analogues of GABA: XV. Preparation and resolution of some potent cyclopentene and cyclopentane derivatives.Aust. J. Chem.39, 855–864 (1986).
  • Chebib M , DukeRK, AllanRD, JohnstonGA. The effects of cyclopentane and cyclopentene analogues of GABA at recombinant GABAC receptors. Eur. J. Pharmacol.430, 185–192 (2001).
  • O‘Hagan D . Understanding organofluorine chemistry. An introduction to the C–F bond.Chem. Soc. Rev.37, 308–319 (2008).
  • Sun AM , LankinDC, HardcastleK, SnyderJP. 3-fluoropiperidines and N-methyl-3-fluoropiperidinium salts. The persistence of axial fluorine. Chem. Eur. J.11, 1579–1591 (2005).
  • Gooseman NE , O‘HaganD, PeachMJ, SlawinAM, TozerDJ, YoungRJ. An electrostatic gauche effect in β-fluoro- and β-hydroxy- N-ethylpyridinium cations. Angew. Chemie. Int. Ed.46, 5904–5908 (2007).
  • Singh RP , ShreeveJM. Nucleophilic fluorination of amino alcohols and diols using deoxofluor.J. Fluorine Chem.116, 23–26 (2002).
  • O‘Hagan D , RzepaHS, SchülerM, SlawinAM. The vicinal difluoro motif. The synthesis and conformation of erythro- and threo- diastereoisomers of 1,2-difluorodiphenylethanes, 2,3-difluorosuccinic acids and their derivatives. Beilstein J. Org. Chem.2, 19 (2006).
  • Morgenthaler M , SchweizerE, Hoffmann-RöderAet al. Predicting and tuning physicochemical properties in lead optimisation: amine basicities. ChemMedChem 2, 1100–1115 (2007).
  • Callachan H , CottrellGA, HatherNY, LambertJJ, MooneyJM, PetersJJ. Modulation of the GABAA receptor by projesterone metabolites. Proc. R. Soc. London B231, 359–369 (1987).
  • Seal RP , EdwardsRH. Functional implications of neurotransmitter co-release: glutamate and GABA share the load.Curr. Opin. Pharmacol.6, 114–119 (2006).
  • Silverman RB , LevyMA. Substituted 4-aminobutanoic acids. Substrates for γ-aminobutyric acid α-ketoglutaric acid aminotransferase.J. Biol. Chem.256, 11565–11568 (1981).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.