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

Gábor Paragi, Lajos Kovács, Zoltán Kupihár, János Szolomájer, Botond Penke, Célia Fonseca Guerra, F. Matthias Bickelhaupt

Research output: Contribution to journalArticle

13 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)119-126
Number of pages8
JournalNew Journal of Chemistry
Volume35
Issue number1
DOIs
Publication statusPublished - Jan 2011

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

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