ArticleJournal of the American Chemical Society2013
Hydroxyl ion addition to one-electron oxidized thymine: unimolecular interconversion of C5 to C6 OH-adducts.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 43 citations in OpenAlex.
- Cellular and Molecular Mechanisms of Oxidative DNA Damage and Repair.Medicina (Kaunas, Lithuania) · 2025Review
- Ne-22 Ion-Beam Radiation Damage to DNA: From Initial Free Radical Formation to Resulting DNA-Base Damage.ACS omega · 2021Article
- Electron-Induced Repair of 2'-Deoxyribose Sugar Radicals in DNA: A Density Functional Theory (DFT) Study.International journal of molecular sciences · 2021Article
- One Way Traffic: Base-to-Backbone Hole Transfer in Nucleoside Phosphorodithioate.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Genotoxic effects of PMEnvironmental geochemistry and health · 2019Article
- Independent Generation of Reactive Intermediates Leads to an Alternative Mechanism for Strand Damage Induced by Hole Transfer in Poly(dA-T) Sequences.Journal of the American Chemical Society · 2018Article
- Direct observation of the oxidation of DNA bases by phosphate radicals formed under radiation: a model of the backbone-to-base hole transfer.Physical chemistry chemical physics : PCCP · 2018Article
- Independent Generation and Reactivity of Thymidine Radical Cations.The Journal of organic chemistry · 2017Article
- Modulating the Catalytic Activity of Cerium Oxide Nanoparticles with the Anion of the Precursor Salt.The journal of physical chemistry. C, Nanomaterials and interfaces · 2017Article
- Prehydrated One-Electron Attachment to Azido-Modified Pentofuranoses: Aminyl Radical Formation, Rapid H-Atom Transfer, and Subsequent Ring Opening.The journal of physical chemistry. B · 2017Article
- Pyrimidine Nucleobase Radical Reactivity in DNA and RNA.Radiation physics and chemistry (Oxford, England : 1993) · 2016Article
- π-Radical to σ-Radical Tautomerization in One-Electron-Oxidized 1-Methylcytosine and Its Analogs.The journal of physical chemistry. B · 2015Article
- 5-Thiocyanato-2'-deoxyuridine as a possible radiosensitizer: electron-induced formation of uracil-C5-thiyl radical and its dimerization.Physical chemistry chemical physics : PCCP · 2015Article
- One-electron oxidation of gemcitabine and analogs: mechanism of formation of C3' and C2' sugar radicals.Journal of the American Chemical Society · 2014Article
- Presolvated electron reactions with methyl acetoacetate: electron localization, proton-deuteron exchange, and H-atom abstraction.Molecules (Basel, Switzerland) · 2014Article
- Reactions of 5-methylcytosine cation radicals in DNA and model systems: thermal deprotonation from the 5-methyl group vs. excited state deprotonation from sugar.International journal of radiation biology · 2014Article
- One-electron oxidation reactions of purine and pyrimidine bases in cellular DNA.International journal of radiation biology · 2014Review
- π- vs σ-radical states of one-electron-oxidized DNA/RNA bases: a density functional theory study.The journal of physical chemistry. B · 2013Article
- Formation of S-Cl phosphorothioate adduct radicals in dsDNA S-oligomers: hole transfer to guanine vs disulfide anion radical formation.Journal of the American Chemical Society · 2013Article
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8 authors at 2 institutions in 1 country.
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Abstract
In this work, addition of OH(-) to one-electron oxidized thymidine (dThd) and thymine nucleotides in basic aqueous glasses is investigated. At pHs ca. 9-10 where the thymine base is largely deprotonated at N3, one-electron oxidation of the thymine base by Cl(2)(•-) at ca. 155 K results in formation of a neutral thyminyl radical, T(-H)·. Assignment to T(-H)· is confirmed by employing (15)N substituted 5'-TMP. At pH ≥ ca. 11.5, formation of the 5-hydroxythymin-6-yl radical, T(5OH)·, is identified as a metastable intermediate produced by OH(-) addition to T(-H)· at C5 at ca. 155 K. Upon further annealing to ca. 170 K, T(5OH)· readily converts to the 6-hydroxythymin-5-yl radical, T(6OH)·. One-electron oxidation of N3-methyl-thymidine (N3-Me-dThd) by Cl(2)(•-) at ca. 155 K produces the cation radical (N3-Me-dThd(•+)) for which we find a pH dependent competition between deprotonation from the methyl group at C5 and addition of OH(-) to C5. At pH 7, the 5-methyl deprotonated species is found; however, at pH ca. 9, N3-Me-dThd(•+) produces T(5OH)· that on annealing up to 180 K forms T(6OH)·. Through use of deuterium substitution at C5' and on the thymine base, that is, specifically employing [5',5"-D,D]-5'-dThd, [5',5"-D,D]-5'-TMP, [CD(3)]-dThd and [CD(3),6D]-dThd, we find unequivocal evidence for T(5OH)· formation and its conversion to T(6OH)·. The addition of OH(-) to the C5 position in T(-H)· and N3-Me-dThd(•+) is governed by spin and charge localization. DFT calculations predict that the conversion of the "reducing" T(5OH)· to the "oxidizing" T(6OH)· occurs by a unimolecular OH group transfer from C5 to C6 in the thymine base. The T(5OH)· to T(6OH)· conversion is found to occur more readily for deprotonated dThd and its nucleotides than for N3-Me-dThd. In agreement, calculations predict that the deprotonated thymine base has a lower energy barrier (ca. 6 kcal/mol) for OH transfer than its corresponding N3-protonated thymine base (14 kcal/mol).
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