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5,6-Dihydropyrimidine Peroxyl Radical Reactivity in DNA

[Image: see text] Nucleobase radicals are a major family of reactive species produced in DNA as a result of oxidative stress. Two such radicals, 5-hydroxy-5,6-dihydrothymidin-6-yl radical (1) and 5,6-dihydrouridin-6-yl radical (5), were independently generated within chemically synthesized oligonucl...

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Autores principales: San Pedro, Joanna Maria N., Greenberg, Marc M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3980663/
https://www.ncbi.nlm.nih.gov/pubmed/24579910
http://dx.doi.org/10.1021/ja412562p
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author San Pedro, Joanna Maria N.
Greenberg, Marc M.
author_facet San Pedro, Joanna Maria N.
Greenberg, Marc M.
author_sort San Pedro, Joanna Maria N.
collection PubMed
description [Image: see text] Nucleobase radicals are a major family of reactive species produced in DNA as a result of oxidative stress. Two such radicals, 5-hydroxy-5,6-dihydrothymidin-6-yl radical (1) and 5,6-dihydrouridin-6-yl radical (5), were independently generated within chemically synthesized oligonucleotides from photochemical precursors. Neither nucleobase radical produces direct strand breaks or alkali-labile lesions in single or double stranded DNA. The respective peroxyl radicals, resulting from O(2) trapping, add to 5′-adjacent nucleobases, with a preference for dG. Distal dG’s are also oxidatively damaged by the peroxyl radicals. Experiments using a variety of sequences indicate that distal damage occurs via covalent modification of the 5′-adjacent dG, but there is no evidence for electron transfer by the nucleobase peroxyl radicals.
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spelling pubmed-39806632015-02-28 5,6-Dihydropyrimidine Peroxyl Radical Reactivity in DNA San Pedro, Joanna Maria N. Greenberg, Marc M. J Am Chem Soc [Image: see text] Nucleobase radicals are a major family of reactive species produced in DNA as a result of oxidative stress. Two such radicals, 5-hydroxy-5,6-dihydrothymidin-6-yl radical (1) and 5,6-dihydrouridin-6-yl radical (5), were independently generated within chemically synthesized oligonucleotides from photochemical precursors. Neither nucleobase radical produces direct strand breaks or alkali-labile lesions in single or double stranded DNA. The respective peroxyl radicals, resulting from O(2) trapping, add to 5′-adjacent nucleobases, with a preference for dG. Distal dG’s are also oxidatively damaged by the peroxyl radicals. Experiments using a variety of sequences indicate that distal damage occurs via covalent modification of the 5′-adjacent dG, but there is no evidence for electron transfer by the nucleobase peroxyl radicals. American Chemical Society 2014-02-28 2014-03-12 /pmc/articles/PMC3980663/ /pubmed/24579910 http://dx.doi.org/10.1021/ja412562p Text en Copyright © 2014 American Chemical Society
spellingShingle San Pedro, Joanna Maria N.
Greenberg, Marc M.
5,6-Dihydropyrimidine Peroxyl Radical Reactivity in DNA
title 5,6-Dihydropyrimidine Peroxyl Radical Reactivity in DNA
title_full 5,6-Dihydropyrimidine Peroxyl Radical Reactivity in DNA
title_fullStr 5,6-Dihydropyrimidine Peroxyl Radical Reactivity in DNA
title_full_unstemmed 5,6-Dihydropyrimidine Peroxyl Radical Reactivity in DNA
title_short 5,6-Dihydropyrimidine Peroxyl Radical Reactivity in DNA
title_sort 5,6-dihydropyrimidine peroxyl radical reactivity in dna
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3980663/
https://www.ncbi.nlm.nih.gov/pubmed/24579910
http://dx.doi.org/10.1021/ja412562p
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