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Issue 18, 2013
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Addressing the competitive formation of tandem DNA lesions by a nucleobase peroxyl radical: a DFT-D screening

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Abstract

The presence of two vicinal single-nucleotide oxidative lesions constitutes a pitfall case for DNA repair. Quantum mechanics calculations are performed to elucidate the formation of peroxyl-bridged adducts, where a purine and a pyrimidine base become covalently tethered. A dispersion-corrected density functional theory (DFT-D) screening along the 32 possible adducts built by a combination of the four different nucleobases outlines that guanine is a better tandem partner than adenine, in line with experimental data. In contrast, cytosine and thymine have an overall comparable reactivity as revealed by a highly localized spin density. For a given purine and pyrimidine combination, our computational approach also sketches some differences concerning the syn vs. anti configurations and the orientation strand.

Graphical abstract: Addressing the competitive formation of tandem DNA lesions by a nucleobase peroxyl radical: a DFT-D screening

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Publication details

The article was received on 07 Feb 2013, accepted on 12 Mar 2013 and first published on 12 Mar 2013


Article type: Paper
DOI: 10.1039/C3OB40280K
Org. Biomol. Chem., 2013,11, 3038-3045

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    Addressing the competitive formation of tandem DNA lesions by a nucleobase peroxyl radical: a DFT-D screening

    C. Dupont, C. Patel, J. L. Ravanat and E. Dumont, Org. Biomol. Chem., 2013, 11, 3038
    DOI: 10.1039/C3OB40280K

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