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

Nucleosides, Nucleotides & Nucleic Acids
Casimir L DowdAllen S Yang

Abstract

Zebularine (1-(beta-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.

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Citations

Apr 18, 2015·Chembiochem : a European Journal of Chemical Biology·Marina TanasovaShana J Sturla
Jul 30, 2009·The Journal of Physical Chemistry. B·Lalitha SelvamFeng Wang

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Software Mentioned

NEMESIS
NASDAC
AMBER8
Pyrosequencer

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