The effect of cytosine methylation on its halogen-bonding properties

被引：11

作者：

Marin-Luna, Marta ^{[1
]}

Alkorta, Ibon ^{[1
]}

Elguero, Jose ^{[1
]}

机构：

[1] CSIC, Inst Quim Med, Juan de la Cierva 3, E-28006 Madrid, Spain

来源：

COMPUTATIONAL AND THEORETICAL CHEMISTRY | 2016年 / 1076卷

关键词：

DNA methylation; DNA-bases tautomerism; Halogen bond; Molecular electrostatic potential; MP2; calculations; BASE-PAIRING ENERGIES; DOT-N BONDS; DNA METHYLATION; ELECTRON-DENSITY; EPIGENETIC CONTROL; RARE TAUTOMERS; GENOMIC DNA; MOTIF; DERIVATIVES; STABILITY;

D O I：

10.1016/j.comptc.2015.12.007

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

This study shows the influence of a 5-methyl substituent on the interaction between 1-methylcytosine, 1,5-dimethylcytosine, 1-methyluracil and 1-methylthymine and dichloride (Cl-2) and fluorine chloride (CIF). The methyl derivatives were selected because of the important role played by a methyl group at position 5 of the pyrimidine ring on the biological properties of nucleobases. Besides binding energies obtained at the MP2/aug-cc-pVDZ level, a variety of theoretical methods were used to analyze the structures of the different minima obtained. A total of 116 complexes have been studied. (C) 2015 Elsevier B.V. All rights reserved.

引用

页码：101 / 108

页数：8

共 69 条

[1] Role of the Arabidopsis DNA glycosylase/lyase ROS1 in active DNA demethylation [J].

Agius, Fernanda ;

Kapoor, Avnish ;

Zhu, Jian-Kang .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (31) :11796-11801

[2] Comparison of models to correlate electron density at the bond critical point and bond distance [J].

Alkorta, I ;

Barrios, L ;

Rozas, I ;

Elguero, J .

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2000, 496 :131-137

[3] Characterizing Traditional and Chlorine-Shared Halogen Bonds in Complexes of Phosphine Derivatives with CIF and Cl2 [J].

Alkorta, Ibon ;

Elguero, Jose ;

Del Bene, Janet E. .

JOURNAL OF PHYSICAL CHEMISTRY A, 2014, 118 (23) :4222-4231

[4] All Five Forms of Cytosine Revealed in the Gas Phase [J].

Alonso, Jose L. ;

Vaquero, Vanesa ;

Pena, Isabel ;

Lopez, Juan C. ;

Mata, Santiago ;

Caminati, Walther .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (08) :2331-2334

[5] ATOMS IN MOLECULES [J].

BADER, RFW .

ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (01) :9-15

[6] On the Reliability of Pure and Hybrid DFT Methods for the Evaluation of Halogen, Chalcogen, and Pnicogen Bonds Involving Anionic and Neutral Electron Donors [J].

Bauza, Antonio ;

Alkorta, Ibon ;

Frontera, Antonio ;

Elguero, Jose .

JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2013, 9 (11) :5201-5210

[7] Fundamental aspects of the nucleic acid i-motif structures [J].

Benabou, S. ;

Avino, A. ;

Eritja, R. ;

Gonzalez, C. ;

Gargallo, R. .

RSC ADVANCES, 2014, 4 (51) :26956-26980

[8] How to Distinguish Methyl-Cytosine from Cytosine with High Fidelity [J].

Bianchi, Caterina ;

Zangi, Ronen .

JOURNAL OF MOLECULAR BIOLOGY, 2012, 424 (3-4) :215-224

[9] Molecular biology - Methylation talk between histones and DNA [J].

Bird, A .

SCIENCE, 2001, 294 (5549) :2113-2115

[10] CPG-RICH ISLANDS AND THE FUNCTION OF DNA METHYLATION [J].

BIRD, AP .

NATURE, 1986, 321 (6067) :209-213

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