Deamination of lysine as a marker for nitrite-protein reactions

Nitrite-Modified Extracellular Matrix Proteins Deleteriously Affect Retinal Pigment Epithelial Cell Function and Viability: A Comparison Study with Nonenzymatic Glycation Mechanisms

“…49 Nitrite causes lysine residue deamination and nitrates tyrosine residues at physiological pH. 21,50 Nitrite not only modifies some residues of proteins, but it also disrupts the protein three-dimensional structures. 51 In model system experiments similar to those developed for nonenzymatic glycation, nitritetreated type I collagen increases visible light absorption, fluorescence, and protein cross-linking.…”

Chemical Modifications of Peptides and Their Impact on Food Properties

“…Especially, much attention has been paid to the formation of nitrosamines derived from peptides, compounds with strong carcinogenic activity. The formation of nitrosamines has been shown to take place at the N -terminal amino group and at the side chains of tryptophan, − lysine, , and arginine , in peptides. The rate of the reaction increases with decreasing pH. , According to Bonnett and Holleyhead, under acidic conditions, nitrite yields the electrophilic nitrosating species NO + or its equivalents H 2 NO 2 + or N 2 O 3 .…”

“…Especially, much attention has been paid to the formation of nitrosamines derived from peptides, compounds with strong carcinogenic activity. The formation of nitrosamines has been shown to take place at the N-terminal amino group 131 and at the side chains of tryptophan, 132À134 lysine, 131,135 and arginine 131,136 in peptides. The rate of the reaction increases with decreasing pH.…”

Nitrite anions induce nitrosative deamination of peptides and proteins

“…The reaction of nitrous acid with primary amines proceeds through an unstable diazonium intermediate and produces nitrogen and a carbocation unless the diazo group is attached directly to a benzene ring. However, only a few studies have been reported on reactions of nitrite anions with amino groups in proteins/peptides 17–22. It was found that nitrite reacted with amino acid to generate alpha‐hydroxy acid and alpha‐halo acids 18.…”

“…It was found that nitrite reacted with amino acid to generate alpha‐hydroxy acid and alpha‐halo acids 18. Using amino acid analysis, Maerker and coworkers found that reactions of nitrite with polylysine led to deamination of lysine to form hydroxynorleucines 19. Manning and coworkers suggested that N‐terminal groups of some proteins can be modified by nitric oxide 20.…”