Acid-base properties of the nucleic-acid model 2'-deoxyguanylyl(5'-->3')-2'-deoxy-5'-guanylate, d(pGpG)3-, and of related guanine derivatives

Organic & Biomolecular Chemistry
Bernd KnoblochRoland K O Sigel

Abstract

The dinucleotide d(pGpG) is an often employed DNA model to study various kinds of interactions between DNA and metal ions, but its acid-base properties were not yet described in detail. In this study the six deprotonation reactions of H4[d(pGpG)]+ are quantified. The acidity constants for the release of the first proton from the terminal P(O)(OH)2 group (pKa = 0.65) and for one of the (N7)H+ sites (pKa = 2.4) are estimated. The acidity constants of the remaining four deprotonation reactions were measured by potentiometric pH titrations in aqueous solution (25 degrees C; I = 0.1 M, NaNO3): The pKa values for the deprotonations of the second (N7)H+, the P(O)2(OH)-, and the two (N1)H sites are 2.98, 6.56, 9.54 and 10.11, respectively. Based on these results we show how to estimate acidity constants for related systems that have not been studied, e.g. pGpG, which is involved in the initiation step of a rotavirus RNA polymerase. The relevance of our results for nucleic acids in general is briefly indicated.

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Citations

Sep 9, 2015·Luminescence : the Journal of Biological and Chemical Luminescence·Feixiang ChengHongju Yin
Dec 15, 2015·Chemistry : a European Journal·Filip Šebesta, Jaroslav V Burda
Jun 21, 2008·Chemistry : a European Journal·Ariel MuchaRoland K O Sigel
Oct 29, 2009·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·M Paula DenofrioAndrés H Thomas
Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chryssostomos Chatgilialoglu
Jan 11, 2007·Chemical Reviews·Roland K O Sigel, Anna Marie Pyle
Feb 19, 2008·Journal of the American Chemical Society·Gabriela PetroselliAndrés H Thomas
Mar 1, 2007·Journal of the American Chemical Society·Carla P Da CostaLincoln G Scott

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