Long-Lived 4-Oxo-2-enal-Derived Apparent Lysine Michael Adducts Are Actually the Isomeric 4-Ketoamides

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• 作者：Xiaochun Zhu ; Lawrence M. Sayre
• 刊名：Chemical Research in Toxicology
• 出版年：2007
• 出版时间：February 2007
• 年：2007
• 卷：20
• 期：2
• 页码：165 - 170
• 全文大小：128K
• 年卷期：v.20,no.2(February 2007)
• ISSN：1520-5010

文摘

There has been significant recent interest in the protein reactivity and biological activity of 4-oxo-2-nonenal (ONE), the 4-keto cousin of HNE. Despite the ability of HNE to form at least metastable Michaeladducts with protein Lys residues, mass spectrometric evidence for the existence of apparent ONE-LysMichael adducts is not supported by preparative solution studies. We herein show that the m+154 adductson Lys residues that persist upon incubating with ONE represent the isomeric 4-ketoamides. The sametype of 4-ketoamide represents the apparent Michael adduct on Lys residues formed by the carboxy-terminating ONE-like 4-oxo-2-enal arising along with ONE from the oxidation of linoleic acid.