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Issue 41, 2014
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Oxidative damage of aromatic dipeptides by the environmental oxidants NO2˙ and O3

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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.

Graphical abstract: Oxidative damage of aromatic dipeptides by the environmental oxidants NO2˙ and O3

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Article information


Submitted
25 Jul 2014
Accepted
02 Sep 2014
First published
02 Sep 2014

Org. Biomol. Chem., 2014,12, 8280-8287
Article type
Paper

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

L. F. Gamon, J. M. White and U. Wille, Org. Biomol. Chem., 2014, 12, 8280
DOI: 10.1039/C4OB01577K

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