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Niles JC, Burney S, Singh SP, et al. Peroxynitrite reaction products of 3',5'-di-O-acetyl-8-oxo-7, 8-dihydro-2'-deoxyguanosine. Proc Natl Acad Sci U S A. 1999;96(21):11729-34doi: 10.1073/pnas.96.21.11729.
Niles, J. C., Burney, S., Singh, S. P., Wishnok, J. S., & Tannenbaum, S. R. (1999). Peroxynitrite reaction products of 3',5'-di-O-acetyl-8-oxo-7, 8-dihydro-2'-deoxyguanosine. Proceedings of the National Academy of Sciences of the United States of America, 96(21), 11729-34. https://doi.org/10.1073/pnas.96.21.11729
Niles, J C, et al. "Peroxynitrite reaction products of 3',5'-di-O-acetyl-8-oxo-7, 8-dihydro-2'-deoxyguanosine." Proceedings of the National Academy of Sciences of the United States of America vol. 96,21 (1999): 11729-34. doi: https://doi.org/10.1073/pnas.96.21.11729
Niles JC, Burney S, Singh SP, Wishnok JS, Tannenbaum SR. Peroxynitrite reaction products of 3',5'-di-O-acetyl-8-oxo-7, 8-dihydro-2'-deoxyguanosine. Proc Natl Acad Sci U S A. 1999 Oct 12;96(21):11729-34. doi: 10.1073/pnas.96.21.11729. PMID: 10518518; PMCID: PMC18354.
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Proc Natl Acad Sci U S A. 1999 Oct 12;96(21):11729-34. doi: 10.1073/pnas.96.21.11729.

Peroxynitrite reaction products of 3',5'-di-O-acetyl-8-oxo-7, 8-dihydro-2'-deoxyguanosine.

Proceedings of the National Academy of Sciences of the United States of America

J C Niles, S Burney, S P Singh, J S Wishnok, S R Tannenbaum

Affiliations

  1. Division of Bioengineering and Environmental Health, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.

PMID: 10518518 PMCID: PMC18354 DOI: 10.1073/pnas.96.21.11729

Abstract

Of the DNA bases, peroxynitrite (ONOO-) is most reactive toward 2'-deoxyguanosine (dGuo), but even more reactive with 8-oxo-7, 8-dihydro-2'-deoxyguanosine (8-oxodGuo), requiring a 1,000-fold excess of dGuo to provide 50% protection against the reaction with 8-oxodGuo. Therefore, it seems reasonable that 8-oxodGuo is a potentially important target in DNA and that the structures of the reaction products with ONOO- should be characterized. Using 3', 5'-di-O-Ac-8-oxodGuo as a model compound, the reaction products with ONOO- have been isolated and identified under simulated physiological reaction conditions (phosphate/bicarbonate buffer at pH 7.2). The major reaction product, II, is unstable and undergoes base-mediated hydrolysis to 2,5-diaminoimidazol-4-one, IIa, and 3-(3, 5-di-O-Ac-2-deoxy-beta-D-erythro-pentofuranosyl)-5-iminoimidazolidine -2,4-dione, IIb. The latter compound further hydrolyzes to 3-(3, 5-di-O-Ac-2-deoxy-beta-D-erythro-pentofuranosyl)oxaluric acid, IIc. Other products include 3-(3, 5-di-O-Ac-2-deoxy-beta-D-erythro-pentofuranosyl)-2,4,6-trioxo-[1,3, 5]triazinane-1-carboxamidine, I, which further hydrolyzes to 1-(3, 5-di-O-Ac-2-deoxy-beta-D-erythro-pentofuranosyl)cyanuric acid, Ia. 1-(3,5-di-O-Ac-2-deoxy-beta-D-erythro-pentofuranosyl)parabanic acid, III, is a minor product that also may contribute to formation of IIc. The major products formed in these reactions are biologically uncharacterized but are similar to modified DNA bases that have been shown to be both premutagenic and blocks to DNA polymerization.

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