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• W2914013239 endingPage "3418" @default.
• W2914013239 startingPage "3405" @default.
• W2914013239 abstract "Kinetic and computational data reveal a complex behavior of the important environmental free radical oxidant NO3• in its reactions with aliphatic amino acids and di- and tripeptides, suggesting that attack at the amide N-H bond in the peptide backbone is a highly viable pathway, which proceeds through a proton-coupled electron transfer (PCET) mechanism with a rate coefficient of about 1 × 106 M-1 s-1 in acetonitrile. Similar rate coefficients were determined for hydrogen abstraction from the α-carbon and from tertiary C-H bonds in the side chain. The obtained rate coefficients for the reaction of NO3• with aliphatic di- and tripeptides suggest that attack occurs at all of these sites in each individual amino acid residue, which makes aliphatic peptide sequences highly vulnerable to NO3•-induced oxidative damage. No evidence for amide neighboring group effects, which have previously been found to facilitate radical-induced side-chain damage in phenylalanine, was found for the reaction of NO3• with side chains in aliphatic peptides." @default.
• W2914013239 created "2019-02-21" @default.
• W2914013239 creator A5044255109 @default.
• W2914013239 creator A5062352558 @default.
• W2914013239 date "2019-02-11" @default.
• W2914013239 modified "2023-09-24" @default.
• W2914013239 title "Oxidative Damage in Aliphatic Amino Acids and Di- and Tripeptides by the Environmental Free Radical Oxidant NO₃^•: The Role of the Amide Bond Revealed by Kinetic and Computational Studies" @default.
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• W2914013239 doi "https://doi.org/10.1021/acs.joc.8b03224" @default.
• W2914013239 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/30742433" @default.
• W2914013239 hasPublicationYear "2019" @default.
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