Pairing strength and proton characters of the N7,N9-dimethylated GC and AT base pairs: a density functional theory investigation

Xing, Dan; Chen, Xiaohua; Bu, Yuxiang

doi:10.1039/b702640d

Cited by 4 publications

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“…Considering the above situation it is surprising to find that there are only a few experimental studies that deal with the effects exerted by copper bound to a certain site of a nucleobase on other nearby sites. ,, Although several theoretical studies have considered the interaction of guanine, adenine, uracil, and thiouracil with transition-metal cations (Ni + , Cu + , Cu 2+ ) ,,, and investigated the acidities of adenine and adenine derivatives, ,,– to the best of our knowledge, no theoretical calculations have been carried out on the deprotonation of Cu + −adenine and Cu 2+ −adenine. In this paper, we mainly focus our attention on the influence of Cu + and Cu 2+ coordination on the acidities of multiple sites in adenine.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study on the Gas-Phase Acidity of Multiple Sites of Cu⁺−Adenine and Cu²⁺−Adenine Complexes

et al. 2008

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The acidities of multiple sites in Cu + -adenine and Cu 2+ -adenine complexes have been investigated theoretically. To compare, the acidities of adenine (A) and adenine radical cation (A •+ ) have also been included. The results clearly indicate that the acidities of C-H and N-H groups in Cu +/2+ -adenine are significantly enhanced relative to the neutral adenine. The acidic order for a given site on adenine and adenine derivatives is as follows: Cu 2+ -adenine > A •+ > Cu + -adenine > A. For Cu + -adenine and Cu 2+ -adenine, N3-coordination exhibits N9-H acid, and N1-and N7-coordination exhibits N6-H a and N6-H b acid, respectively. Additionally, it is found that C2-H group is surprisingly acidic in the coordination complexes. Calculations in aqueous solution reveal that our results can be extrapolated to aqueous solution. Analyses of the electronic properties interpret the highest acidity of Cu 2+ -adenine among the adenine derivatives studied. Also, Electrostatic potential calculations of [A(-H + )]and [A(-H + )] • indicate that the removal of H a or H b from the amino group favors the bidentate coordination, which provides a dative bond from the deprotonated N and the original coordination ligand to copper ion besides the electrostatic interaction between them and thereby stabilizes the [A(-H + )] -/[A(-H + )] • . NBO analysis confirms the electrostatic potential result.

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Section: Introductionmentioning

confidence: 99%

Theoretical Study on the Gas-Phase Acidity of Multiple Sites of Cu⁺−Adenine and Cu²⁺−Adenine Complexes

et al. 2008

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Deprotonation studies of Cu+–guanine and Cu2+–guanine complexes by theoretical investigation

Xing¹,

Tan²,

Jiang³

et al. 2011

Computational and Theoretical Chemistry

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Molecular criteria for mutagenesis by DNA methylation: Some computational elucidations

Salam

Devi

Lyngdoh

2018

Mutation Research/Fundamental and Molecular Mechanisms of Mutag

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Pairing strength and proton characters of the N7,N9-dimethylated GC and AT base pairs: a density functional theory investigation

Cited by 4 publications

References 58 publications

Theoretical Study on the Gas-Phase Acidity of Multiple Sites of Cu⁺−Adenine and Cu²⁺−Adenine Complexes

Theoretical Study on the Gas-Phase Acidity of Multiple Sites of Cu⁺−Adenine and Cu²⁺−Adenine Complexes

Deprotonation studies of Cu+–guanine and Cu2+–guanine complexes by theoretical investigation

Molecular criteria for mutagenesis by DNA methylation: Some computational elucidations

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Pairing strength and proton characters of the N7,N9-dimethylated GC and AT base pairs: a density functional theory investigation

Cited by 4 publications

References 58 publications

Theoretical Study on the Gas-Phase Acidity of Multiple Sites of Cu+−Adenine and Cu2+−Adenine Complexes

Theoretical Study on the Gas-Phase Acidity of Multiple Sites of Cu+−Adenine and Cu2+−Adenine Complexes

Deprotonation studies of Cu+–guanine and Cu2+–guanine complexes by theoretical investigation

Molecular criteria for mutagenesis by DNA methylation: Some computational elucidations

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Theoretical Study on the Gas-Phase Acidity of Multiple Sites of Cu⁺−Adenine and Cu²⁺−Adenine Complexes

Theoretical Study on the Gas-Phase Acidity of Multiple Sites of Cu⁺−Adenine and Cu²⁺−Adenine Complexes