Preparation of d₅-labeled (E)-4-hydroxy-2-nonenal and its reaction with model peptide

Abstract

It is well known that (E)-4-hydroxy-2-nonenal is an oxidative metabolite of lipid such as polyunsaturated fatty acids and acts as an important biomarker of some diseases and aging. (E)-4-Hydroxy-2-nonenal reacts with protein containing cysteine, lysine and histidine to afford a modified protein via Michael addition and subsequent cyclization. In order to develop the quantitative analysis of modified protein by using deuterium-labeled compound, we prepared d₅-labeled (E)-4-hydroxy-2-nonenal and its reaction with a model peptide was investigated. MALDI-TOFMS of the labeled and unlabeled modified peptides showed the ion peaks reacted with three molecules of (E)-4-hydroxy-2-nonenal.

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