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 for this work

18 Citations (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

Original language	English
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	41
Pages (from-to)	8280-8287
Number of pages	8
ISSN	1477-0520
DOIs	https://doi.org/10.1039/c4ob01577k
Publication status	Published - 7 Nov 2014
Externally published	Yes

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title = "Oxidative damage of aromatic dipeptides by the environmental oxidants NO2 and O3",

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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T1 - Oxidative damage of aromatic dipeptides by the environmental oxidants NO2 and O3

AU - Gamon, L. F.

AU - White, J. M.

AU - Wille, U.

PY - 2014/11/7

Y1 - 2014/11/7

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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C2 - 25207524

AN - SCOPUS:84907646531

SN - 1477-0520

VL - 12

SP - 8280

EP - 8287

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 41

ER -

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

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