2011
DOI: 10.1016/j.freeradbiomed.2011.05.002
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Myoglobin-H2O2 catalyzes the oxidation of β-ketoacids to α-dicarbonyls: Mechanism and implications in ketosis

Abstract: Acetoacetate (AA) and 2-methylacetoacetate (MAA) are accumulated in metabolic disorders such as diabetes and isoleucinemia. Here we examine the mechanism of AA and MAA aerobic oxidation initiated by myoglobin (Mb)/H2O2. We propose a chemiluminescent route involving a dioxetanone intermediate whose thermolysis yields triplet α-dicarbonyl species (methylglyoxal and diacetyl). The observed ultraweak chemiluminescence increased linearly upon raising the concentration of either Mb (10–500 μM) or AA (10–100 mM). Oxy… Show more

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Cited by 12 publications
(10 citation statements)
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“…The generation of methylglyoxal and diacetyl, putatively in the triplet state, by the oxidation of myoglobin-catalyzed aerobic oxidation of acetoacetate and 2-methylacetoacetate, respectively, was reported more recently70.…”
Section: Discussionmentioning
confidence: 91%
“…The generation of methylglyoxal and diacetyl, putatively in the triplet state, by the oxidation of myoglobin-catalyzed aerobic oxidation of acetoacetate and 2-methylacetoacetate, respectively, was reported more recently70.…”
Section: Discussionmentioning
confidence: 91%
“…In recent years, the interaction of protein with small molecules has become a hot spot in the fields of chemistry, biology, and medicine [5][6][7]. As common model proteins, bovine serum albumin (BSA) [8], lysozyme (LYS) [9], myoglobin (MB) [10], and catalase (CAT) [11] are widely applied to the study of protein-small molecule interaction. Accordingly, many methods have been utilized to investigate this hot topic, such as fluorescence spectroscopy [12], resonance light scattering [13], circular dichroism [14], nuclear magnetic resonance spectroscopy [15], and chemiluminescence (CL) with flow injection (FI) technique [16].…”
Section: Introductionmentioning
confidence: 99%
“…For example, acetoacetate and 2-methylacetoacetate are accumulated in metabolic disorders such as diabetes and isoleucinemia. 18 β-Keto acids are also very useful as synthons, since they can act as stabilized ketone enolates and react with suitable electrophilic substrates. 19 Thus they have been proved valuable building blocks for the synthesis of several classes of compounds with different biological activities.…”
mentioning
confidence: 99%