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Solvent effects on hydrogen bonds in Watson-Crick, mismatched, and modified DNA base pairs

We have theoretically analyzed a complete series of Watson-Crick and mismatched DNA base pairs, both in gas phase and in solution. Solvation causes a weakening and lengthening of the hydrogen bonds between the DNA bases because of the stabilization of the lone pairs involved in these bonds. We have also shown that chlorouracil can mimic the behavior of thymine, and thus perfectly incorporate into a DNA strand, in nice agreement with recent experiments involving Escherichia coli. Moreover, through quantitative bond analyses in the framework of Kohn-Sham DFT, we have further consolidated the notion that donor-acceptor orbital interactions between lone-pairs and N-H σ * orbitals contribute in the same order of magnitude to the hydrogen-bond strength as electrostatic interactions

We thank the following organizations for financial support: the HPC-Europa2 Transnational Access program of the European Union, the Netherlands Organization for Scientific Research (NWO), the Ministerio de Ciencia e Innovacion (MICINN, project number CTQ2011-25086) and the National Research School Combination - Catalysis (NRSC-C). Financial support from MICINN (Ministry of Science and Innovation, Spain) and the FEDER fund (European Fund for Regional Development) was provided by grant UNGI08-4E-003. J.P. thanks the MICINN for the Ramon y Cajal contract

© Computational and Theoretical Chemistry, 2012, vol. 998, p. 57-63

Elsevier

Author: Poater i Teixidor, Jordi
Swart, Marcel
Fonseca Guerra, Célia
Bickelhaupt, Friedrich Matthias
Date: 2012
Abstract: We have theoretically analyzed a complete series of Watson-Crick and mismatched DNA base pairs, both in gas phase and in solution. Solvation causes a weakening and lengthening of the hydrogen bonds between the DNA bases because of the stabilization of the lone pairs involved in these bonds. We have also shown that chlorouracil can mimic the behavior of thymine, and thus perfectly incorporate into a DNA strand, in nice agreement with recent experiments involving Escherichia coli. Moreover, through quantitative bond analyses in the framework of Kohn-Sham DFT, we have further consolidated the notion that donor-acceptor orbital interactions between lone-pairs and N-H σ * orbitals contribute in the same order of magnitude to the hydrogen-bond strength as electrostatic interactions
We thank the following organizations for financial support: the HPC-Europa2 Transnational Access program of the European Union, the Netherlands Organization for Scientific Research (NWO), the Ministerio de Ciencia e Innovacion (MICINN, project number CTQ2011-25086) and the National Research School Combination - Catalysis (NRSC-C). Financial support from MICINN (Ministry of Science and Innovation, Spain) and the FEDER fund (European Fund for Regional Development) was provided by grant UNGI08-4E-003. J.P. thanks the MICINN for the Ramon y Cajal contract
Format: application/pdf
Citation: 2210271X
Document access: http://hdl.handle.net/10256/11438
Language: eng
Publisher: Elsevier
Collection: MICINN/PN 2012-2014/CTQ2011-25086
Reproducció digital del document publicat a: http://dx.doi.org/10.1016/j.comptc.2012.06.003
Articles publicats (D-Q)
Is part of: © Computational and Theoretical Chemistry, 2012, vol. 998, p. 57-63
Rights: Tots els drets reservats
Subject: Funcional de densitat, Teoria del
Density functionals
ADN -- Estructura
DNA structure
Enllaços d’hidrogen
Hydrogen bonding
Title: Solvent effects on hydrogen bonds in Watson-Crick, mismatched, and modified DNA base pairs
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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