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Theoretica chimica acta

, Volume 36, Issue 4, pp 317–328 | Cite as

Molecular orbital studies on the conformation of GABA (γ-aminobutyric acid)

The isolated molecule and the solvent effect
  • Bernard Pullman
  • Hélène Berthod
Commentationes

Abstract

In distinction to Extended Hückel Theory which predicts as the most stable conformation of free zwitterionic GABA a totally extended form, PCILO and SCF ab initio studies show that the intrinsically preferred conformation of the isolated molecule is a highly folded one, resulting from strong interactions between the two charged ends. Computations are also carried out for hydrated GABA in the “supermolecule” approach allowing moreover for the flexibility of binding of some of the water molecules of the first hydration shell. They predict the coexistence in solution of a large number of conformations showing different degrees of folding (or extension), a result confirmed by recent NMR studies. This and a number of similar results show that we have to adapt our thinking on the role of conformations in pharmacological activity to this situation, which was frequently obscured by the more abundant results of X-ray crystallography yielding a single conformation.

Key words

γ-aminobutyric acid conformation of ∼ 

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Copyright information

© Springer-Verlag 1975

Authors and Affiliations

  • Bernard Pullman
    • 1
  • Hélène Berthod
    • 1
  1. 1.Institut de Biologie Physico-ChimiqueLaboratoire de Biochimie ThéoriqueParis

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