Issue 1, 2011
From the journal:

New Journal of Chemistry

Neutral and positively charged new purine tetramer structures: a computational study of xanthine and uric acid derivatives

Gábor Paragi,*a   Lajos Kovács,b   Zoltán Kupihár,b   János Szolomájer,b   Botond Penke,ab   Célia Fonseca Guerrac  and  F. Matthias Bickelhauptc  

* Corresponding authors

a Supramolecular and Nanostructured Materials Research Group of the Hungarian Academy of Sciences at the University of Szeged, Dóm tér 8, Szeged, Hungary
E-mail: paragi@sol.cc.u-szeged.hu
Fax: +36 62545971
Tel: +36 62544593

b Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, Hungary

c Department of Theoretical Chemistry and Amsterdam Center for Multiscale Modeling (ACMM), Scheikundig Laboratorium der Vrije Universteit Amsterdam, De Boelelaan 1083, NL-1081 HV Amsterdam, The Netherlands

Abstract

New tetramer structures, based on 9-methylxanthine (Xa), 9-methylxanthine protonated at N7 (XaH+) and 9-methyluric acid (Ua), were investigated by high-level density functional calculations. We have found that homo- and heterotetrads (XaH+)4, (XaH+–Xa)2, (XaH+–Ua)2 carrying positive charges can be formed by low barrier hydrogen bonds. Systems with zero charge [(Xa)4, (Xa–Ua)2, (Ua)4] were also constructed, investigated and compared to the guanine tetrad [(G)4]. It was shown that the new tetramers can bind cations and anions without the necessity of stacking interactions. Application of the calculated systems in higher-ordered structures (e.g. quadruplexes) is promising with or without intercalating ions.

Graphical abstract: Neutral and positively charged new purine tetramer structures: a computational study of xanthine and uric acid derivatives

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Article information

DOI
https://doi.org/10.1039/C0NJ00613K
Article type
Paper
Submitted
06 Aug 2010
Accepted
20 Sep 2010
First published
15 Oct 2010

New J. Chem., 2011,35, 119-126

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Neutral and positively charged new purine tetramer structures: a computational study of xanthine and uric acid derivatives

G. Paragi, L. Kovács, Z. Kupihár, J. Szolomájer, B. Penke, C. Fonseca Guerra and F. M. Bickelhaupt, New J. Chem., 2011, 35, 119 DOI: 10.1039/C0NJ00613K

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