دورية أكاديمية
Protonated primary amines induced thymine quintets studied by electrospray ionization mass spectrometry and density functional theory calculations
| العنوان: | Protonated primary amines induced thymine quintets studied by electrospray ionization mass spectrometry and density functional theory calculations |
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| المؤلفون: | Qin, Zhen, Qiu, Bo, Sun, Jiamu, Zhao, Wenbo, Luo, Hai |
| المساهمون: | Luo, H (reprint author), Peking Univ, Coll Chem & Mol Engn, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China., Peking Univ, Coll Chem & Mol Engn, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China. |
| المصدر: | EI ; PubMed ; SCI |
| بيانات النشر: | journal of mass spectrometry |
| سنة النشر: | 2014 |
| المجموعة: | Peking University Institutional Repository (PKU IR) / 北京大学机构知识库 |
| مصطلحات موضوعية: | 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 |
| الوصف: | 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=8e1609b174ce4e31116a60747a720701Test ; Biochemical Research Methods ; Chemistry, Analytical ; Spectroscopy ; SCI(E) ; EI ; PubMed ; 3 ; ARTICLE ; hluo@pku.edu.cn ; 4 ; 266-273 ; 49 |
| نوع الوثيقة: | journal/newspaper |
| اللغة: | English |
| ردمك: | 978-0-00-333950-5 0-00-333950-5 |
| تدمد: | 1076-5174 1096-9888 |
| العلاقة: | JOURNAL OF MASS SPECTROMETRY.2014,49,(4),266-273.; 653816; http://hdl.handle.net/20.500.11897/149709Test; WOS:000333950500002 |
| DOI: | 10.1002/jms.3334 |
| الإتاحة: | https://doi.org/20.500.11897/149709Test https://doi.org/10.1002/jms.3334Test https://hdl.handle.net/20.500.11897/149709Test |
| رقم الانضمام: | edsbas.48A79633 |
| قاعدة البيانات: | BASE |
| ردمك: | 9780003339505 0003339505 |
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| تدمد: | 10765174 10969888 |
| DOI: | 10.1002/jms.3334 |