Fragmentation-Rearrangement of Peptide Backbones Mediated by the Air Pollutant NO2 (.)

Chemistry : a European Journal
Luke F GamonUta Wille

Abstract

The fragmentation-rearrangement of peptide backbones mediated by nitrogen dioxide, NO2 (.) , was explored using di-, tri-, and tetrapeptides 8-18 as model systems. The reaction, which is initiated through nonradical N-nitrosation of the peptide bond, shortens the peptide chain by the expulsion of one amino acid moiety with simultaneous fusion of the remaining molecular termini through formation of a new peptide bond. The relative rate of the fragmentation-rearrangement depends on the nature of the amino acids and decreases with increasing steric bulk at the α carbon in the order Gly>Ala>Val. Peptides that possessed consecutive aromatic side chains only gave products that resulted from nitrosation of the sterically less congested N-terminal amide. Such backbone fragmentation-rearrangement occurs under physiologically relevant conditions and could be an important reaction pathway for peptides, in which sections without readily oxidizable side chains are exposed to the air pollutant NO2 (.) . In addition to NO2 (.) -induced radical oxidation processes, this outcome shows that ionic reaction pathways, in particular nitrosation, should be factored in when assessing NO2 (.) reactivity in biological systems.

References

Jan 1, 1984·Toxicology and Applied Pharmacology·M G MustafaD E Gardner
Dec 1, 1994·Environmental Health Perspectives·J A LastH Witschi
May 20, 1994·Toxicology·R E Huie
Aug 15, 1997·The Journal of Biological Chemistry·B S Berlett, E R Stadtman
Mar 11, 2000·American Journal of Respiratory and Critical Care Medicine·J F HuntB Gaston
May 15, 2001·American Journal of Respiratory Cell and Molecular Biology·R L PersingerY M Janssen-Heininger
Apr 27, 2002·The Journal of Organic Chemistry·Ron W DarbeauEdson V Perez
Jul 29, 2003·Occupational and Environmental Medicine·Frank J Kelly
Mar 12, 2004·Proceedings of the National Academy of Sciences of the United States of America·Nathan S BryanMartin Feelisch
Feb 1, 2005·Biochimica Et Biophysica Acta·Michael J Davies
May 19, 2009·The Journal of Physical Chemistry. B·Shinichi EnamiA J Colussi
Aug 24, 2011·Journal of Toxicology·Maura Lodovici, Elisabetta Bigagli
Mar 28, 2013·Occupational and Environmental Medicine·Marie-Élise ParentAlexandre Liautaud
Mar 20, 2014·Annual Review of Public Health·Kirk R SmithUNKNOWN HAP CRA Risk Expert Group
Sep 11, 2014·Organic & Biomolecular Chemistry·L F GamonU Wille

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Citations

Sep 14, 2016·International Forum of Allergy & Rhinology·Dara R AdamsJayant M Pinto
Oct 19, 2016·Accounts of Chemical Research·Luke F Gamon, Uta Wille
Feb 20, 2016·Chemical Communications : Chem Comm·A N ZalewskiU Wille

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