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γ-Diketone reactivity with lysine. Reaction of 2,5-hexanedione (2,5-HD, upper) and 1,2-diacetylbenzene (1,2-DAB, lower) with lysine to form dimethyl-pyrrole and -isoindole adducts, respectively, which form dimers that oxidize and polymerize to cross-link targeted proteins. The colored pigments that result appear to be associated with the dimer formation. Antioxidants block 1,2-DAB-induced cytotoxicity of SHSY5Y cells.95
