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


Knobloch, B; Sigel, H; Okruszek, A; Sigel, Roland K O (2006). 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, 4(6):1085-1090.

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 ºC; 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 shortly indicated.

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 ºC; 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 shortly indicated.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:21 March 2006
Deposited On:08 Aug 2013 07:32
Last Modified:18 May 2017 08:03
Publisher:RSC Publishing
ISSN:1477-0520
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1039/b517904a

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