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Ab Initio Calculations of the Pairing of Four Canonical DNA Bases with Three Thymine Derivatives Generated by Hydroxyl Radical in Anaerobic Conditions

Cysewski P.

Polish Journal of Chemistry

2000

Vol. 74, nr 2

245-256

The coding properties of three hydroxyl radical induced thyine derivatives; 5-hydroxy-6-hydrothyine (1), 5,6-dihydrothymine (2) and 6-hydroxy-5,6-dihydrothymine (3) were characterized by ab initio HF/6-31 G, HF/6-31 G**//HF/6-31G and SCI-PCM/6-31G**//HF/6-31G quantum chemistry calculations. All studied derivatives ay have potential miscoding character, which strongly depends on the polarity of the environment. Under non-polar conditions all analyzed thymine derivatives are able to pair with guanine, what may result in the T-C transition. Additionally, I is able to form stable pairs with cytosine and adenine. Compound 3 is capable to pair with all four canonical DNA bases. All these pairs are more stable than standard AT pair. In polar environment the pairing potential of studied thymine derivatives is significantly reduced. However, the mispairing potential is usually the same and reained significant, especially for 6-hydroxy-6-hydrothymine.