Oxidative damage of aromatic dipeptides by the environmental oxidants NO2 and O3

L. F. Gamon; J. M. White; U. Wille

doi:10.1039/c4ob01577k

Oxidative damage of aromatic dipeptides by the environmental oxidants NO₂ and O₃

L. F. Gamon^*, J. M. White, U. Wille

^*Corresponding author af dette arbejde

18 Citationer (Scopus)

Abstract

Irreversible oxidative damage at both aromatic side chains and dipeptide linkage occurs in the aromatic N- and C-protected dipeptides 7-11 upon exposure to the environmental pollutants NO₂ and O₃. The reaction proceeds through initial oxidation of the aromatic ring by in situ generated NO₃, or by NO₂, respectively, which leads to formation of nitroaromatic products. The indole ring in Phe-Trp undergoes oxidative cyclization to a pyrroloindoline. An important reaction pathway for dipeptides with less oxidisable aromatic side chains proceeds through fragmentation of the peptide bond with concomitant acyl migration. This process is likely initiated by an ionic reaction of the amide nitrogen with the NO₂ dimer, N₂O₄. This journal is

Originalsprog	Engelsk
Tidsskrift	Organic and Biomolecular Chemistry
Vol/bind	12
Udgave nummer	41
Sider (fra-til)	8280-8287
Antal sider	8
ISSN	1477-0520
DOI	https://doi.org/10.1039/c4ob01577k
Status	Udgivet - 7 nov. 2014
Udgivet eksternt	Ja

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Citationsformater

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abstract = "Irreversible oxidative damage at both aromatic side chains and dipeptide linkage occurs in the aromatic N- and C-protected dipeptides 7-11 upon exposure to the environmental pollutants NO2 and O3. The reaction proceeds through initial oxidation of the aromatic ring by in situ generated NO3, or by NO2, respectively, which leads to formation of nitroaromatic products. The indole ring in Phe-Trp undergoes oxidative cyclization to a pyrroloindoline. An important reaction pathway for dipeptides with less oxidisable aromatic side chains proceeds through fragmentation of the peptide bond with concomitant acyl migration. This process is likely initiated by an ionic reaction of the amide nitrogen with the NO2 dimer, N2O4. This journal is",

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AU - Gamon, L. F.

AU - White, J. M.

AU - Wille, U.

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N2 - Irreversible oxidative damage at both aromatic side chains and dipeptide linkage occurs in the aromatic N- and C-protected dipeptides 7-11 upon exposure to the environmental pollutants NO2 and O3. The reaction proceeds through initial oxidation of the aromatic ring by in situ generated NO3, or by NO2, respectively, which leads to formation of nitroaromatic products. The indole ring in Phe-Trp undergoes oxidative cyclization to a pyrroloindoline. An important reaction pathway for dipeptides with less oxidisable aromatic side chains proceeds through fragmentation of the peptide bond with concomitant acyl migration. This process is likely initiated by an ionic reaction of the amide nitrogen with the NO2 dimer, N2O4. This journal is

AB - Irreversible oxidative damage at both aromatic side chains and dipeptide linkage occurs in the aromatic N- and C-protected dipeptides 7-11 upon exposure to the environmental pollutants NO2 and O3. The reaction proceeds through initial oxidation of the aromatic ring by in situ generated NO3, or by NO2, respectively, which leads to formation of nitroaromatic products. The indole ring in Phe-Trp undergoes oxidative cyclization to a pyrroloindoline. An important reaction pathway for dipeptides with less oxidisable aromatic side chains proceeds through fragmentation of the peptide bond with concomitant acyl migration. This process is likely initiated by an ionic reaction of the amide nitrogen with the NO2 dimer, N2O4. This journal is

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