BAKER, Andrew, Lukáš ŽÍDEK, Don WIESLER a Milos NOVOTNY. Reaction of N-Acetylglycyllysine Methyl Ester with 2-Alkenals: An Alternative Model for Covalent Modification of Proteins. Chemical Research in Toxicology. Washington, DC (USA): American Chemical Society, 1998, roč. 11, č. 7, s. 730-740. ISSN 08993228X. |
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@article{205691, author = {Baker, Andrew and Žídek, Lukáš and Wiesler, Don and Novotny, Milos}, article_location = {Washington, DC (USA)}, article_number = {7}, keywords = {LOW-DENSITY-LIPOPROTEIN; MASS-SPECTROMETRY; ADDUCTS; PEROXIDATION; ALDEHYDES; HISTIDINE; GLYCINE; LYSINE}, issn = {08993228X}, journal = {Chemical Research in Toxicology}, title = {Reaction of N-Acetylglycyllysine Methyl Ester with 2-Alkenals: An Alternative Model for Covalent Modification of Proteins}, volume = {11}, year = {1998} }
TY - JOUR ID - 205691 AU - Baker, Andrew - Žídek, Lukáš - Wiesler, Don - Novotny, Milos PY - 1998 TI - Reaction of N-Acetylglycyllysine Methyl Ester with 2-Alkenals: An Alternative Model for Covalent Modification of Proteins JF - Chemical Research in Toxicology VL - 11 IS - 7 SP - 730 EP - 730 PB - American Chemical Society SN - 08993228X KW - LOW-DENSITY-LIPOPROTEIN KW - MASS-SPECTROMETRY KW - ADDUCTS KW - PEROXIDATION KW - ALDEHYDES KW - HISTIDINE KW - GLYCINE KW - LYSINE N2 - Among the various reactions of lipid peroxidation products with proteins, 2-alkenals have been shown to react extensively with the epsilon-amino group of lysine residues [Zidek et al. (1997) Chem. Res. Toxicol. 10, 702-710]. To obtain additional information about the kinetic and mechanistic aspects of this modification, a model peptide (N-acetylglycyllysine O-methyl ester) was reacted with 2-hexenal. The reaction products were characterized through a combination of NMR and MS techniques. The structural elucidation efforts have shown the formation of pyridinium salts through the reaction of two or more alkenals with one amino group. Kinetic data were obtained using a continuous infusion of the reaction mixture into an electrospray ionization mass spectrometer. A mechanism is proposed that; offers an alternative model for the formation of stable protein cross-links. The reaction progresses through a Schiff base intermediate to form a dihydropyridine species which can be alternatively reduced to form various 3,4- or 2,5-substituted pyridinium species or react with another Schiff base to form a trialkyl-substituted pyridinium structure. The stoichiometry of this structure (aldehyde/amine) is 3:2, in contrast to the widely accepted 1:2. Therefore, it represents another possible crosslinking mechanism for bifunctional products of lipid peroxidation. ER -
BAKER, Andrew, Lukáš ŽÍDEK, Don WIESLER a Milos NOVOTNY. Reaction of N-Acetylglycyllysine Methyl Ester with 2-Alkenals: An Alternative Model for Covalent Modification of Proteins. \textit{Chemical Research in Toxicology}. Washington, DC (USA): American Chemical Society, 1998, roč.~11, č.~7, s.~730-740. ISSN~08993228X.
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