Published in

Royal Society of Chemistry, Physical Chemistry Chemical Physics, 3(16), p. 1101-1110, 2014

DOI: 10.1039/c3cp53885k

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The DNA-forming properties of 6-selenoguanine

Journal article published in 2014 by Ignacio Faustino, Carles Curutchet ORCID, F. Javier Luque ORCID, Modesto Orozco
This paper is available in a repository.
This paper is available in a repository.

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Abstract

We present here an exhaustive characterization of the structure and properties of 6-selenoguanine, an isoster of guanine, and the impact of its introduction in DNA. This study reports the results of state-of-the-art quantum mechanical calculations and atomistic molecular dynamics simulations carried out to shed light on the impact of the replacement of guanine (G) by 6-selenoguanine (SeG) in different forms of DNA. The results point out that the G → SeG substitution leads to stable DNA duplex, antiparallel triplex and G-quadruplex structures, though local distortions are also found. These structural changes affect the thermodynamic stability of the mutation leading to a clear destabilization for all studied systems. Interestingly, the lowest effect has been found when the mutation was placed in the triplex-forming oligonucleotide strand in a reverse Hoogsteen orientation, which favours the antiparallel triplex formation regarding the G-tetraplex formation. Detailed QM studies strongly suggest that SeG impacts the HOMO-LUMO gap and accordingly the transfer properties of DNA, opening the way to modulate the conductivity properties of non-natural DNAs.