Hydrogen Atom Abstraction Reactions of the Sugar Moiety of 2′-Deoxyguanosine with an OH Radical: A Quantum Chemical Study

被引：12

作者：

Shukla, P. K. ^{[1
]}

Kumar, N. ^{[1
]}

Mishra, P. C. ^{[1
]}

机构：

[1] Banaras Hindu Univ, Dept Phys, Varanasi 221005, Uttar Pradesh, India

来源：

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY | 2011年 / 111卷 / 09期

关键词：

DNA; hydrogen atom abstraction reactions; sugar radicals; 2 '-deoxyguanosine; OH radical; DENSITY-FUNCTIONAL THERMOCHEMISTRY; CONTINUUM SOLVATION MODELS; AB-INITIO; DEOXYRIBOSE RADICALS; HYDROXYL RADICALS; SINGLE-CRYSTALS; INDUCED DAMAGE; EXACT-EXCHANGE; DNA BACKBONE; STRAND;

D O I：

10.1002/qua.22494

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：

Mechanisms of hydrogen atom abstraction reactions of the sugar moiety of 2'-deoxyguanosine with an OH radical were investigated using the B3LYP and BHandHLYP functionals of density functional theory and the second order Moller-Plesset Perturbation (MP2) theory in gas phase and aqueous media. The 6-31+G* and AUG-cc-pVDZ basis sets were used. Gibbs free barrier energies and rate constants of the reactions in aqueous media suggest that an OH radical would abstract the hydrogen atoms of the sugar moiety of 2'-deoxyguanosine in the following order of preference: H5' approximate to H5 '' > H3' > H4' > H1' approximate to H2' > H2 '', the rate constant for H5' abstraction being 10(3)-10(5) times greater than that for H2 '' at the different levels of theory. Relative stabilities of the different deoxyribose radicals are also discussed. The most and least favored hydrogen abstraction reactions found here are in agreement with experimental observation. (C) 2010 Wiley Periodicals, Inc. Int J Quantum Chem 111: 2160-2169, 2011

引用

页码：2160 / 2169

页数：10

共 50 条

[21] Direct dynamics study on hydrogen abstraction reaction of CF3CF2CH2OH with OH radical
Wang, Ying
Liu, Jing-yao
Li, Ze-sheng
Wang, Li
Wu, Jia-yan
Sun, Chia-Chung
JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (17): : 5853 - 5859
[22] BIMOLECULAR REACTIONS OF DISTONIC IONS - PROTON-TRANSFER AND HYDROGEN-ATOM ABSTRACTION WITH CH2OH2+
MOURGUES, P
AUDIER, HE
LEBLANC, D
HAMMERUM, S
ORGANIC MASS SPECTROMETRY, 1993, 28 (10): : 1098 - 1100
[23] Direct ab initio dynamics studies of the hydrogen abstraction reactions of hydrogen atom with n-propyl radical and isopropyl radical
Li, QS
Zhang, Y
Zhang, SW
JOURNAL OF MOLECULAR MODELING, 2005, 11 (01) : 41 - 47
[24] Direct ab initio dynamics studies of the hydrogen abstraction reactions of hydrogen atom with n-propyl radical and isopropyl radical
Qian Shu Li
Yue Zhang
Shaowen Zhang
Journal of Molecular Modeling , 2005, 11 : 41 - 47
[25] Theoretical and kinetic study of the hydrogen atom abstraction reactions of ethyl esters with hydrogen radicals
Wang, Quan-De, 1600, Elsevier B.V., Netherlands (616-617):
[26] Analyzing hydroxyl radical accessibility related to hydrogen abstraction in a DNA sugar moiety using molecular dynamics simulations
Kawanami, Ryuta
Fujiwara, Susumu
Yonetani, Yoshiteru
Aso, Tsukasa
AIP ADVANCES, 2024, 14 (10)
[27] Theoretical and kinetic study of the hydrogen atom abstraction reactions of ethyl esters with hydrogen radicals
Wang, Quan-De
Wang, Xing-Jian
Liu, Zi-Wu
Kang, Guo-Jun
CHEMICAL PHYSICS LETTERS, 2014, 616 : 109 - 114
[28] Influence of the double bond on the hydrogen abstraction reactions of methyl esters with hydrogen radical: an ab initio and chemical kinetic study
Wang, Quan-De
Zhang, Weidong
RSC ADVANCES, 2015, 5 (84) : 68314 - 68325
[29] Highly accurate quantum chemical study of the OH radical
Ma, HT
Bian, WS
Zheng, SJ
Meng, LP
ACTA CHIMICA SINICA, 2005, 63 (04) : 263 - 268
[30] Theoretical and Kinetic Study of the Hydrogen Atom Abstraction Reactions of Esters with HO2 Radicals
Mendes, Jorge
Zhou, Chong-Wen
Curran, Henry J.
JOURNAL OF PHYSICAL CHEMISTRY A, 2013, 117 (51): : 14006 - 14018

← 1 2 3 4 5 →