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• W2059042377 endingPage "240" @default.
• W2059042377 startingPage "229" @default.
• W2059042377 abstract "The pentapeptide methionine-enkephalin (Met-enk) is a natural opiate that inhibits signals of pain. The N-terminal tyrosyl residue is important in the recognition of the peptide by its receptor. In oxidative stress, this residue can be oxidized by reactive oxygen species. The one-electron oxidation of Met-enk and of tert-butoxycarbonyl-methionine-enkephalin (Boc-Met-enk) was studied by γ- and pulse radiolysis in the absence and in the presence of superoxide radical anions (O2−) and oxygen, using azidyl radicals as oxidants. Without oxygen, both peptides behaved similarly. The tyrosyl radical resulting from the oxidation of tyrosyl residue produced the dimer linked by dityrosines. Methionine was also oxidized to its sulfoxide; however, this reaction is of minor importance. When O2− was present, it added to tyrosyl radical giving a hydroperoxide. For Met-enk, this adduct cyclized via an intramolecular Michael addition of the amine on the aromatic ring. Conversely, for Boc-Met-enk, the adduct eliminated oxygen which led to 97% regeneration of the nonmodified peptide. Blocking the terminal amine group had thus a key role in protection of the tyrosyl residue. This finding might be exploited in the search for new pain inhibitors." @default.
• W2059042377 created "2016-06-24" @default.
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• W2059042377 date "2007-07-01" @default.
• W2059042377 modified "2023-10-18" @default.
• W2059042377 title "Superoxide radical anions protect enkephalin from oxidation if the amine group is blocked" @default.
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• W2059042377 doi "https://doi.org/10.1016/j.freeradbiomed.2007.04.006" @default.
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