Issue 9, 2011

Damage of aromatic amino acids by the atmospheric free radical oxidant NO3˙ in the presence of NO2˙, N2O4, O3 and O2

Abstract

Analysis of the products formed in the reaction of NO3˙ with the N- and C-protected aromatic amino acids 1–5, which was performed under conditions that simulate exposure of biosurfaces to environmental pollutants, revealed insight how this important atmospheric free-radical oxidant can cause irreversible damage. In general, NO3˙ induced electron transfer at the aromatic ring is the exclusive initial pathway in a multi-step sequence, which ultimately leads to nitroaromatic compounds. In the reaction of NO3˙ with tryptophan 5 tricyclic products 12 and 13 are formed through an intramolecular, oxidative cyclization involving the amide moiety. In addition to this, strong indication for formation of N-nitrosamides was obtained, which likely result from reaction with N2O4 through an independent non-radical pathway.

Graphical abstract: Damage of aromatic amino acids by the atmospheric free radical oxidant NO3˙ in the presence of NO2˙, N2O4, O3 and O2

Supplementary files

Article information

Article type
Paper
Submitted
16 Dec 2010
Accepted
07 Feb 2011
First published
16 Mar 2011

Org. Biomol. Chem., 2011,9, 3380-3385

Damage of aromatic amino acids by the atmospheric free radical oxidant NO3˙ in the presence of NO2˙, N2O4, O3 and O2

C. Goeschen, N. Wibowo, J. M. White and U. Wille, Org. Biomol. Chem., 2011, 9, 3380 DOI: 10.1039/C0OB01186J

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