Journal Article10.1021/JF950837R
Reactivity of Lysine Moieties toward γ-Hydroxy-α,β-unsaturated Epoxides: A Model Study on Protein−Lipid Oxidation Product Interaction
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TL;DR: In this article, the reactivity of γ-hydroxy-α,β-unsaturated epoxides toward lysine moieties is investigated, employing trans-4,5-epoxy-trans-2-hexen-1-ol (EH) as a model substrate and propylamine or N2-acetyl-l-lysine 4-methylcoumar-7-ylamide (AcLys-MCA) as model reagents for protein-bound lysines.
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Abstract: Epoxyols are generally accepted as crucial intermediates in lipid oxidation. The reactivity of γ-hydroxy-α,β-unsaturated epoxides toward lysine moieties is investigated, employing trans-4,5-epoxy-trans-2-hexen-1-ol (EH) as a model substrate and propylamine or N2-acetyl-l-lysine 4-methylcoumar-7-ylamide (AcLys-MCA) as model reagents for protein-bound lysine. Independent syntheses are reported for EH and AcLys-MCA. Reaction of the amine components with EH in THF yields 4-(propylamino)-trans-2-hexene-1,5-diol and N2-acetyl-N6-(1,5-dihydroxy-trans-2-hexen-4-yl)-l-lysine 4-methylcoumaryl-7-amide, respectively. Unequivocal structural characterization of the products prove the epoxy ring cleavage to proceed by a true SN2 mechanism. Incubation of EH with propylamine and AcLys-MCA in aqueous medium at 37 °C shows the turnover to decrease with lower pHs. From reaction of EH (100 mM) with AcLys-MCA (50 mM) under physiological conditions (pH 7.4), 3% of the lysine moieties can be identified in the form of N2-acetyl-N...
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