Oxidative damage of aromatic dipeptides by the environmental oxidants NO2 and O3
Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
Standard
Oxidative damage of aromatic dipeptides by the environmental oxidants NO2 and O3. / Gamon, L. F.; White, J. M.; Wille, U.
I: Organic and Biomolecular Chemistry, Bind 12, Nr. 41, 07.11.2014, s. 8280-8287.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
Harvard
APA
Vancouver
Author
Bibtex
}
RIS
TY - JOUR
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
UR - http://www.scopus.com/inward/record.url?scp=84907646531&partnerID=8YFLogxK
U2 - 10.1039/c4ob01577k
DO - 10.1039/c4ob01577k
M3 - Journal article
C2 - 25207524
AN - SCOPUS:84907646531
VL - 12
SP - 8280
EP - 8287
JO - Organic & Biomolecular Chemistry
JF - Organic & Biomolecular Chemistry
SN - 1470-4358
IS - 41
ER -
ID: 194816335