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Nitrite anions induce nitrosative deamination of peptides and proteins
Author(s) -
Deng Haiteng
Publication year - 2006
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.2776
Subject(s) - chemistry , deamination , nitrite , peptide , amino acid , sodium nitrite , combinatorial chemistry , mass spectrometry , lysine , biochemistry , organic chemistry , chromatography , enzyme , nitrate
In the present study, reactions of sodium nitrite with proteins/peptides were characterized with mass spectrometry. The reaction generates two major products: replacement of the amino group by a hydroxyl group and formation of an alkene derivative by loss of a NH 3 group at the N‐terminus and the side chain of lysine residues of proteins/peptides. The reaction proceeds rapidly in weak acidic solution and at 37°C in the presence of a millimolar concentration of nitrite, demonstrating that nitrite induces nitrosative deamination in proteins and peptides. The facile nitrite‐induced modification of amino groups of protein/peptides changes the chemical nature of proteins and may have various applications in peptide synthesis, analytical chemistry, and protein engineering. It also provides information to enhance our understanding of functions of nitrite ions in biology and food preservation. Copyright © 2006 John Wiley & Sons, Ltd.