Agonist responses of (R)- and (S)-3-fluoro-γ-aminobutyric acids suggest an enantiomeric fold for GABA binding to GABAC receptors

Izumi Yamamoto; Gildas P. Deniau; Navnath Gavande; Mary Chebib; Graham A. R. Johnston; David O'Hagan

doi:10.1039/C1CC12141C

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Agonist responses of (R)- and (S)-3-fluoro-γ-aminobutyric acids suggest an enantiomeric fold for GABA binding to GABA_C receptors†

Izumi Yamamoto,^a Gildas P. Deniau,^b Navnath Gavande,^a Mary Chebib,^a Graham A. R. Johnston^c and David O'Hagan*^b

Author affiliations

* Corresponding authors

^a Faculty of Pharmacy, University of Sydney, NSW, Australia

^b University of St Andrews, EASTChem School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife, UK
E-mail: do1@st-andrews.ac.uk
Fax: (+44)1334 463800
Tel: (+44)1334 467171

^c Adrien Albert Laboratory of Medicinal Chemistry, Department of Pharmacology DO6, University of Sydney, NSW, Australia

Abstract

The enantiomers of 3F-GABA were evaluated on GABA_C receptors. Both enantiomers were agonists, with the (R)-enantiomer being an order of magnitude more potent. This result is consistent with a folded binding mode for GABA, a conclusion which suggests a different binding mode to that found in the related but pharmacologically distinct GABA_A receptors.

This article is part of the themed collection: RACI100: Celebrating Australian Chemistry

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Article information

DOI: https://doi.org/10.1039/C1CC12141C
Article type: Communication
Submitted: 14 Apr 2011
Accepted: 25 May 2011
First published: 13 Jun 2011

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Chem. Commun., 2011,47, 7956-7958

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Agonist responses of (R)- and (S)-3-fluoro-γ-aminobutyric acids suggest an enantiomeric fold for GABA binding to GABA_C receptors

I. Yamamoto, G. P. Deniau, N. Gavande, M. Chebib, G. A. R. Johnston and D. O'Hagan, Chem. Commun., 2011, 47, 7956 DOI: 10.1039/C1CC12141C

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