53412-34-3Relevant academic research and scientific papers
Oxidative damage of aromatic dipeptides by the environmental oxidants NO2 and O3
Gamon,White,Wille
, p. 8280 - 8287 (2014)
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
Damage of aromatic amino acids by the atmospheric free radical oxidant NO3 in the presence of NO2, N2O4, O3 and O2
Goeschen, Catrin,Wibowo, Natalia,White, Jonathan M.,Wille, Uta
experimental part, p. 3380 - 3385 (2011/06/20)
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 impor
