Role of the tautomerism of 2-azaadenine and 2-azahypoxanthine in substrate recognition by xanthine oxidase |
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| Authors: | Begoña Hernández Modesto Orozco Francisco J. Luque |
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| Affiliation: | (1) Department of Biochemistry and Molecular Biology, Faculty of Chemistry, University of Barcelona, Martí i Franquès 1, E-08028 Barcelona, Spain;(2) Department of Pharmacy, Section Physical Chemistry, Faculty of Pharmacy, University of Barcelona, Avinguda Diagonal s/n, E-08028 Barcelona, Spain |
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| Abstract: | The tautomerism of 2-azaadenine and 2-hypoxanthine has been examined in the gas phase and in aqueous solution. The tautomerism in the gas phase has been studied by means of semiempirical and ab initio quantum-mechanical computations, as well as density-functional calculations. The influence of the aqueous solvent on the relative stability between tautomers has been estimated from self-consistent reaction field calculations performed with different high-level continuum models. The results provide a detailed picture of the tautomeric preference for these purine bases. The importance of tautomerism in the substrate recognition by xanthine oxidase is discussed. Finally, the rate of oxidation of 2-azaadenine and 2- hypoxanthine by xanthine oxidase is discussed in terms of the recognition model at the enzyme active site. |
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| Keywords: | Xanthine oxidase Molecular recognition Tautomerism Quantum mechanics Xanthine |
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