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

doi:10.1039/c0nj00613k

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

University of Szeged
Vrije Universiteit Amsterdam

Research output: Contribution to journal › Article › peer-review

17 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 language	English
Pages (from-to)	119-126
Number of pages	8
Journal	New Journal of Chemistry
Volume	35
Issue number	1
DOIs	https://doi.org/10.1039/c0nj00613k
Publication status	Published - Jan 2011
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Materials Chemistry

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

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.",

author = "G{\'a}bor Paragi and Lajos Kov{\'a}cs and Zolt{\'a}n Kupih{\'a}r and J{\'a}nos Szolom{\'a}jer and Botond Penke and \{Fonseca Guerra\}, C{\'e}lia and Bickelhaupt, \{F. Matthias\}",

year = "2011",

month = jan,

doi = "10.1039/c0nj00613k",

language = "English",

volume = "35",

pages = "119--126",

journal = "New Journal of Chemistry",

issn = "1144-0546",

publisher = "Royal Society of Chemistry",

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T1 - Neutral and positively charged new purine tetramer structures

T2 - A computational study of xanthine and uric acid derivatives

AU - Paragi, Gábor

AU - Kovács, Lajos

AU - Kupihár, Zoltán

AU - Szolomájer, János

AU - Penke, Botond

AU - Fonseca Guerra, Célia

AU - Bickelhaupt, F. Matthias

PY - 2011/1

Y1 - 2011/1

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/78650447477

U2 - 10.1039/c0nj00613k

DO - 10.1039/c0nj00613k

M3 - Article

AN - SCOPUS:78650447477

SN - 1144-0546

VL - 35

SP - 119

EP - 126

JO - New Journal of Chemistry

JF - New Journal of Chemistry

IS - 1

ER -

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

Abstract

ASJC Scopus subject areas

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