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Title

Unique tautomeric and recognition properties of thioketothymines?

AuthorsFaustino, Ignacio; Aviñó, Anna ; Eritja Casadellà, Ramón ; Marchán, Iván; Luque, Francisco Javier; Orozco, Modesto
KeywordsAb initio method
Aqueous solutions
Carbonyl oxygen
DNA structure
Free-energy calculations
Modified DNA
In-vacuum
Sulfur atoms
Molecular dynamics simulations
Pyrimidine derivatives;
Tautomeric forms
Recognition properties
Theoretical result
DNA
Issue DateSep-2009
PublisherAmerican Chemical Society
CitationJournal of the American Chemical Society
AbstractThe tautomeric and recognition properties of thymine, 2- and 4-thioketothymines have been studied by means of accurate ab initio methods combined with molecular dynamics simulations and free energy calculations. In contrast to previous suggestions in the literature, the replacement of carbonyl oxygens by sulfur atoms does not lead to dramatic changes in tautomeric properties of the pyrimidine derivatives neither in vacuum nor in aqueous solution. Moreover, the presence of thioketothymines induces only mild changes in DNA structure, stability and fidelity. Despite the fact that mismatching can largely stabilize minor tautomeric forms, thioketothymines are found in the canonical thioketo-form irrespective of the paired base. Our theoretical results, confirmed by new experimental studies, describe the complete tautomeric and recognition characteristics of thioketothymines and demonstrate that both 2-thioketo and 4-thioketothymine are excellent molecules to introduce special chemical properties in modified DNA.
Publisher version (URL)DOI: 10.1021/ja904880y
URIhttp://hdl.handle.net/10261/125137
DOI10.1021/ja904880y
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