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

Posted June 8th, 2010 by pschmidtke
TitleTautomerism of xanthine and alloxanthine: a model for substrate recognition by xanthine oxidase
Publication TypeJournal Article
Year of Publication1996
AuthorsHernandez, B, Orozco M, Luque FJ
JournalJournal of computer-aided molecular design
Volume10
Issue6
Pagination535 - 544
Date Published1996/12//
KeywordsBinding Sites; Drug Design; Gases; Models, Chemical; Molecular Structure; Oxypurinol/chemistry; Solutions; Substrate Specificity; Thermodynamics; Water; Xanthine; Xanthine Oxidase/chemistry/metabolism; Xanthines/chemistry
AbstractTautomerism 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 Moller-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.