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Computational study of the reactivity of cytosine derivatives
Author(s) -
Jerbi Jihène,
Springborg Michael
Publication year - 2017
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.24781
Subject(s) - cytosine , reactivity (psychology) , chemistry , hydrogen bond , guanine , demethylation , computational chemistry , dna , hydrogen , gas phase , molecule , stereochemistry , dna methylation , organic chemistry , nucleotide , biochemistry , gene expression , alternative medicine , pathology , gene , medicine
The aim of the present study is to provide computational insight using dispersion‐corrected density‐functional calculations into the reactivity properties of modified cytosine in the gas phase and in aqueous solution, whereby special emphasis is put on systems that are obtained through demethylation and methylation. Since this field is relatively incipient, our goal is to identify relationships between reactivity and stability for the modified compounds to understand their biological functionalities. Our results show that addition of a methyl, hydroxylmethyl, formyl, or carboxyl group reduces the length of the nearest hydrogen bond between the cytosine–guanine (CG) base pair and increases the length of the longest hydrogen bond of the DNA base pair. © 2017 Wiley Periodicals, Inc.