2011
DOI: 10.1071/ch11102
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Oxidative Damage of Thymidines by the Atmospheric Free-Radical Oxidant NO3•

Abstract: Analysis of the products formed in the reaction of nitrate radicals, NO3 •, with the N- and O-methylated and acetylated thymidines 1a and 1b revealed, for the first time, insight regarding how this important atmospheric free-radical oxidant can cause irreversible damage to DNA building blocks. Mechanistic studies indicated that the initial reaction step likely proceeds via NO3 • induced electron transfer at the pyrimidine ring, followed by deprotonation of the methyl group at C5. The oxidation ultima… Show more

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Cited by 4 publications
(9 citation statements)
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“…The observed side-chain oxidation in 3 by NO 3 • is similar to the outcome of the reaction of thymidine nucleosides with NO 3 • , where oxidative transformation of the methyl substituent in the heterocyclic base occurs exclusively [13]. Concentration–time profiles revealed for the latter reactions that formation of a nitrate occurs first, which is converted to an aldehyde and subsequently into a carboxylic acid [13].…”
Section: Resultsmentioning
confidence: 65%
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“…The observed side-chain oxidation in 3 by NO 3 • is similar to the outcome of the reaction of thymidine nucleosides with NO 3 • , where oxidative transformation of the methyl substituent in the heterocyclic base occurs exclusively [13]. Concentration–time profiles revealed for the latter reactions that formation of a nitrate occurs first, which is converted to an aldehyde and subsequently into a carboxylic acid [13].…”
Section: Resultsmentioning
confidence: 65%
“…In experiments where NO 3 • was used in the absence of other radical and non-radical oxidants, NO 3 • was generated at room temperature from cerium(IV) ammonium nitrate (CAN) through photo-induced electron transfer at an irradiation wavelength of λ = 350 nm (Scheme 1) [1113]. …”
Section: Resultsmentioning
confidence: 99%
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