| 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. | |
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MedLine Citation:
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PMID: 17990263 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Gamma-aminobutyric acid or GABA (1) is one of the major inhibitory amino acid neurotransmitters of the central nervous system. This article describes the first synthesis of both the (R)- and (S)- enantiomers 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 GABA(A) receptors; however, they behave quite differently in a whole animal (Xenopus laevis tadpole model). |
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Authors:
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Gildas Deniau; Alexandra M Z Slawin; Tomas Lebl; Fatima Chorki; Jon P Issberner; Tanja van Mourik; Judith M Heygate; Jeremy J Lambert; Lori-An Etherington; Keith T Sillar; David O'Hagan |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Chembiochem : a European journal of chemical biology Volume: 8 ISSN: 1439-7633 ISO Abbreviation: Chembiochem Publication Date: 2007 Dec |
Date Detail:
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Created Date: 2007-12-19 Completed Date: 2008-02-06 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 100937360 Medline TA: Chembiochem Country: Germany |
Other Details:
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Languages: eng Pagination: 2265-74 Citation Subset: IM |
Affiliation:
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School of Chemistry and Centre for Biomolecular Sciences, University of St. Andrews, St. Andrews, Fife, KY16 9ST, Scotland, UK. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Animals Biological Assay Drug Evaluation GABA Agents / chemical synthesis, chemistry, pharmacology Humans Models, Biological* Molecular Structure Stereoisomerism Xenopus laevis / embryology gamma-Aminobutyric Acid / analogs & derivatives*, chemical synthesis, chemistry, pharmacology |
| Grant Support | |
ID/Acronym/Agency:
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//Wellcome Trust |
| Chemical | |
Reg. No./Substance:
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0/3-fluoro-gamma-aminobutryic acid; 0/GABA Agents; 56-12-2/gamma-Aminobutyric Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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