Isoketals: highly reactive gamma-ketoaldehydes formed from the H2-isoprostane pathway
Sean S Davies1, Venkataraman Amarnath, L Jackson Roberts
1Department of Pharmacology, Vanderbilt University, Nashville, TN 37232-6602, USA. sean.davies@vanderbilt.edu
Abstract:
Oxidation of arachidonic acid leads to the formation of highly reactive gamma-ketoaldehydes now termed isoketals. Isoketals react with proteins at a rate that far exceeds other well studied products of lipid peroxidation such as 4-hydroxynonenal and demonstrate a remarkable proclivity to crosslink these proteins. For these reasons, isoketals have the potential to significantly alter protein function and contribute to disease processes. This article reviews the chemistry of isoketal formation, of their adduction to proteins, and of their proclivity to crosslink proteins, as well as their effects on protein function, and their potential role in diseases associated with oxidative injury.
Related Concept Videos
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
α-Alkylation of Ketones via Enolate Ions
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
The carbonyl center is activated by...
Aldehydes and Ketones with Alcohols: Hemiacetal Formation


