The electronic spectra and the H-bonding pattern of the sulfur and selenium substituted guanines

doi:10.1002/jcc.22991

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	The electronic spectra and the H-bonding pattern of the sulfur and selenium substituted guanines
	Wang, Jing 1; Gu, Jiande1,2 ; Leszczynski, Jerzy 1
刊名	JOURNAL OF COMPUTATIONAL CHEMISTRY
	2012-07-15
卷号	33 期号:19 页码:1587-1593
关键词	guanine selenium sulfur electronic spectra
ISSN号	0192-8651
DOI	10.1002/jcc.22991
文献子类	Article
英文摘要	The density functional theory (DFT) with B3LYP, M05-2x, and M06-2x functionals, along with the 6-311+G(d, p) basis set, were used in the study of the UV absorption spectra and the H-bonding pairing patterns of the sulfur and selenium substituted guanines. The time-dependent DFT calculations reveal that the red-shifts of the transition energies predicted for guanine for the first gas-phase observable transition amount to 55 nm for S6mG and 86 nm for Se6mG, respectively. These changes in the transition energies are qualitatively comparable to the experimental data for substituted guanines in DNA. The density deformation map reveals that both sulfur and selenium atoms exhibit lesser conjugated with the purine ring, which leads to the small transition energies in S6mG and Se6mG. The decrease in binding energy (3 kcal/mol) of Se6mGmC as compared to that of mGmC is well related to the observation of the melting temperature difference ?Tm similar to 3.9 degrees C for the Se-DNA versus DNA. The molecular recognition (mGmC pairing) pattern is found to be changed significantly due to the replacement of O6 by S or Se. The substantial basebase plane twisting revealed in this study suggests that the base stacking in the DNA might be interrupted. This study shows that the red-shifts of the transition energies predicted by the M05-2x and M06-2x functionals are close to those revealed by the B3LYP calculations. As M05-2x and M06-2x offer better descriptions for the dispersion interactions, they provide efficient approaches to investigate the influences of the base-stacking on the transition energies. (C) 2012 Wiley Periodicals, Inc.
资助项目	NSF CREST[HRD-0833178] ; Chinese Academy of Sciences[XDA01040000]
WOS关键词	DENSITY-FUNCTIONAL THEORY ; AIM TOPOLOGICAL ANALYSIS ; HYDROGEN-BONDS ; DUPLEX DNA ; HARTREE-FOCK ; AB-INITIO ; 6-THIOGUANINE ; THIOGUANINE ; MOLECULES ; THERMOCHEMISTRY
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-BLACKWELL
WOS记录号	WOS:000304904300001
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/278015]
专题	药物发现与设计中心
通讯作者	Wang, Jing
作者单位	1.Jackson State Univ, Dept Chem, Interdisciplinary Nanotox Ctr, Jackson, MS 39217 USA; 2.Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, Drug Design & Discovery Ctr,State Key Lab Drug Re, Shanghai 201203, Peoples R China
推荐引用方式 GB/T 7714	Wang, Jing,Gu, Jiande,Leszczynski, Jerzy. The electronic spectra and the H-bonding pattern of the sulfur and selenium substituted guanines[J]. JOURNAL OF COMPUTATIONAL CHEMISTRY,2012,33(19):1587-1593.
APA	Wang, Jing,Gu, Jiande,&Leszczynski, Jerzy.(2012).The electronic spectra and the H-bonding pattern of the sulfur and selenium substituted guanines.JOURNAL OF COMPUTATIONAL CHEMISTRY,33(19),1587-1593.
MLA	Wang, Jing,et al."The electronic spectra and the H-bonding pattern of the sulfur and selenium substituted guanines".JOURNAL OF COMPUTATIONAL CHEMISTRY 33.19(2012):1587-1593.