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Nucleic Acids Research, 2000, Vol. 28, No. 24 4873-4883
© 2000 Oxford University Press

Misincorporation of 2'-deoxyoxanosine into DNA: a molecular basis for NO-induced mutagenesis derived from theoretical calculations

Begoña Hernández, Robert Soliva, F. Javier Luque1 and Modesto Orozco*

Departament de Bioquímica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1, Barcelona 08028, Spain and 1Departament de Fisicoquímica, Facultat de Farmàcia, Universitat de Barcelona, Avgda Diagonal sn, Barcelona 08028, Spain

A wide range of theoretical methods, including high level ab initio, density functional, self-consistent reaction field, molecular dynamics and thermodynamic integration calculations, have been used to analyze the mutagenic properties of oxanosine. The major tautomeric forms in the gas phase and aqueous solution have been determined. The ability of oxanosine to recognize thymine and cytosine in the gas phase and in the DNA environment has been compared with that of guanine. A physicochemical explanation for the mutagenic properties of oxanosine is suggested.

* To whom correspondence should be addressed. Modesto Orozco, Tel: +34 93 402 1719; Fax: +34 93 402 1219; Email: modesto{at}luz.bq.ub.es Correspondence may also be addressed to: F. Javier Luque, Tel: +34 93 402 4557; Fax: +34 93 403 5987; Email:javier{at}far1.far.ub.es


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