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A non-empirical molecular orbital study on the relative stabilities of adenine and guanine tautomers

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Abstract

The relative stabilities of a series of adenine and guanine tautomers have been calculated using anab initio Hartree-Fock-Roothaan SCF MO method. The calculated relative stabilities agree in general with the results of earlier semiempirical studies. According to the present study, tautomeric forms with regular Kekulé structure for the six-membered purine ring are the most stable. The amine-imine tautomerization of purine bases is not likely to be responsible for spontaneous mutations in DNA.

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Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, University of Saskatchewan, S7N OWO, Saskatoon, Canada

    Paul G. Mezey

  2. Laboratory of the National Foundation for Cancer Research at the Chair of Theoretical Chemistry, University of Erlangen-Nürnberg, Canada

    Paul G. Mezey

  3. Chair of Theoretical Chemistry, University of Erlangen-Nürnberg, Germany

    Janos J. Ladik

  4. Laboratory of the National Foundation for Cancer Research at the Chair of Theoretical Chemistry, University of Erlangen-Nürnberg, Egerlandstraβe 3, D-8520, Erlangen, Germany

    Janos J. Ladik

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  1. Paul G. Mezey
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  2. Janos J. Ladik
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Mezey, P.G., Ladik, J.J. A non-empirical molecular orbital study on the relative stabilities of adenine and guanine tautomers. Theoret. Chim. Acta 52, 129–145 (1979). https://doi.org/10.1007/BF00634788

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  • DOI: https://doi.org/10.1007/BF00634788

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