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Incorporation of zebularine from its 2′-deoxyribonucleoside triphosphate derivative and activity as a template-coding nucleobase

AutorDowd, Casimir L.; Sutch, Brian T.; Haworth, Ian S.; Márquez, Víctor E.; Yang, Allen; Eritja Casadellà, Ramón
Palabras clave5-Azacytidine
zebularine
DNA methylation
Epigenetics
Enzyme Inhibitors
DNA
Fecha de publicaciónfeb-2008
EditorTaylor & Francis
CitaciónNucleosides, Nucleotides and Nucleic Acids
ResumenZebularine (1-(β-D-ribofuranosyl)-1,2-dihydropyrimidin-2-one) was studied as both a 2 ′-deoxyribosyl 5 ′-triphosphate derivative and as a template incorporated into an oligonucleotide. Using a novel pyrosequencing assay, zebularine acted as cytosine analog and was incorporated into DNA with a template pairing profile most similar to cytosine, pairing with greatest efficiency opposite guanine in the template strand. Guanine was incorporated with greater affinity than adenine opposite a zebularine in the template strand. Computer modeling of base-pairing structures supported a better fit of zebularine opposite guanine than adenine. Zebularine acts as a cytosine analog, which supports its activity as an inhibitor of cytosine methyltransferase.
Versión del editorDOI: 10.1080/15257770701795888
URIhttp://hdl.handle.net/10261/125040
DOI10.1080/15257770701795888
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