Protonated primary amines induced thymine quintets studied by   electrospray ionization mass spectrometry and density functional theory   calculations

doi:10.1002/jms.3334

CORC > 北京大学 > 化学与分子工程学院

	Protonated primary amines induced thymine quintets studied by electrospray ionization mass spectrometry and density functional theory calculations
	Qin, Zhen ; Qiu, Bo ; Sun, Jiamu ; Zhao, Wenbo ; Luo, Hai
刊名	journal of mass spectrometry
	2014
关键词	thymine quintet magic number cluster mass spectrometry density functional theory - stacking interaction supramolecular chemistry PI-PI INTERACTIONS GAS-PHASE DISPERSION CORRECTIONS ALKALI-METALS CROWN-ETHERS COMPLEXES CLUSTERS SERINE HOMOCHIRALITY STABILIZATION
DOI	10.1002/jms.3334
英文摘要	As the novel magic number clusters of nucleobases, the thymine quintets induced by ammonium ion (NH4+), and particularly by its derivatives such as protonated alkyl amines and protonated aryl amines, have been studied by electrospray ionization mass spectrometry (ESI-MS) and density functional theory (DFT) calculations. The DFT-optimized geometry of NH4+ induced thymine quintet ([T-5+NH4](+)) reveals some new features including three additional hydrogen bonds between NH4+ and its surrounding thymine molecules when compared with that of the alkali metal ions induced thymine quintets. In addition, the fourth hydrogen atom of NH4+ is sticking out the assembly, and, thus, it might be replaced by an organic group R to form the protonated primary amine induced thymine quintet ([T-5+R-NH3](+)), a hypothesis that has been confirmed by both DFT calculations and ESI-MS experiments. Furthermore, the relative abilities of the different protonated primary amines for inducing the thymine quintets are investigated by ESI-MS competition experiments, and the results have shown a clear trend of stronger ability as the alkyl chain gets longer or as the aryl ring gets larger for the alkyl amines or the aryl amines. Two basic influence factors are consequently identified: one is the ability of the alkyl amine to accept proton, another is the - stacking interaction between the aryl ring and the -surface of the thymine molecule(s), whose explanations are strongly supported by multiple types of thermochemical data, various control experiments and DFT calculations. Copyright (c) 2014 John Wiley & Sons, Ltd.; http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000333950500002&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=8e1609b174ce4e31116a60747a720701 ; Biochemical Research Methods; Chemistry, Analytical; Spectroscopy; SCI(E); EI; PubMed; 3; ARTICLE; hluo@pku.edu.cn; 4; 266-273; 49
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/149709]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Qin, Zhen,Qiu, Bo,Sun, Jiamu,et al. Protonated primary amines induced thymine quintets studied by electrospray ionization mass spectrometry and density functional theory calculations[J]. journal of mass spectrometry,2014.
APA	Qin, Zhen,Qiu, Bo,Sun, Jiamu,Zhao, Wenbo,&Luo, Hai.(2014).Protonated primary amines induced thymine quintets studied by electrospray ionization mass spectrometry and density functional theory calculations.journal of mass spectrometry.
MLA	Qin, Zhen,et al."Protonated primary amines induced thymine quintets studied by electrospray ionization mass spectrometry and density functional theory calculations".journal of mass spectrometry (2014).