Tautomerism of xanthine and alloxanthine: a model for substrate recognition by xanthine oxidase

Journal of Computer-aided Molecular Design
B HernándezF J Luque

Abstract

Tautomerism of neutral xanthine and alloxanthine has been examined both in the gas phase and in aqueous solution. The tautomeric preference in the gas phase has been studied by means of semiempirical and ab initio quantum-mechanical computations with inclusion of correlation effects at the Møller-Plesset level, and from density-functional calculations. The influence of solvent on the relative stability between tautomers has been estimated from self-consistent reaction field calculations performed with different models. The results provide a detailed picture of tautomerism for these biologically relevant purine bases. The functional implications in the recognition by xanthine oxidase are analyzed from inspection of the interaction patterns of the most stable tautomeric forms. A model for the recognition of these purine derivatives in the enzyme binding site is discussed.

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Citations

Aug 23, 2008·Journal of Molecular Biology·Ioannis PapageorgiouGeorge Diallinas
Nov 21, 2014·Metabolomics : Official Journal of the Metabolomic Society·Ilya GertsmanBruce A Barshop
Apr 22, 2015·Journal of Biomolecular Structure & Dynamics·Vishakha Karnawat, Mrinalini Puranik
Oct 7, 2005·Journal of Enzyme Inhibition and Medicinal Chemistry·Hemlata TamtaAnup K Mukhopadhyay
Apr 12, 2002·Journal of Computational Chemistry·J MuñozF Javier Luque
Oct 7, 2006·Journal of Molecular Modeling·Jordi Muñoz-MuriedasFrancisco Javier Luque
Aug 13, 2005·Molecular Membrane Biology·Sophia GoudelaGeorge Diallinas
Jul 30, 1999·Journal of Biomaterials Science. Polymer Edition·R S LabowJ P Santerre
Feb 19, 2002·Chemical Reviews·Christopher J. Cramer, Donald G. Truhlar
Jun 3, 2010·Journal of Chemical Information and Modeling·Francesca Milletti, Anna Vulpetti
Jan 8, 2004·Journal of the American Chemical Society·José Ramón BlasModesto Orozco

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