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- W1537541495 abstract "Abstract The flavoprotein lactate oxidase (decarboxylating) from Mycobacterium smegmatis catalyzes the formation of two different products from a novel substrate, β-chlorolactate: (a) combined oxidation and decarboxylation to chloroacetate and carbon dioxide (the normal sequence), and (b) intramolecular elimination of the β-chloro group of the substrate to form the keto acid pyruvate. Product composition depends on oxygen. Pyruvate is formed catalytically under anaerobic conditions. Chloroacetate production begins at low levels of oxygen and comprises 70 to 80% of the products at 100% oxygen saturation levels. Oxygen uptake and pyruvate formation are reciprocally related, suggesting a common precursor for the two reaction pathways. The ability of lactate oxidase to catalyze the elimination reaction suggests that catalysis occurs by initial abstraction of the α-hydrogen as a proton, followed by a subsequent 2-electron transfer in oxidation of the substrates. These data are similar to those obtained for reaction of β-chloroamino acid substrates with d- and l-amino acid oxidases (Walsh, C. T., Schonbrunn, A., and Abeles, R. H. (1971) J. Biol. Chem. 246, 6855) and suggest that these three flavoprotein oxidases have similar reaction mechanisms. Evidence for shielding from the solvent of the substratederived α-proton on the enzyme during catalysis was obtained with β-chloro[α-3H]lactate. During the elimination reaction with this substrate in H2O, 30% of the tritium originally present at the carbon was found in the methyl group (β carbon) of the pyruvate formed. The ability of this flavoprotein oxidase to catalyze such direct hydrogen transfer with β-chlorolactate provides indirect evidence for the formation and then the enzyme-catalyzed ketonization of the enol form of pyruvate at the active site during the elimination reaction. When [α-2H]lactate is used as substrate for lactate oxidase a deuterium kinetic isotope effect of 1.7 is noted; when α-3H substrate is used, there is a selection of 3.2 against tritiated substrate molecules, suggesting some transfer of the α-hydrogen is a slow step during catalysis." @default.
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- W1537541495 date "1973-10-01" @default.
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- W1537541495 title "Studies on the Mechanism of Action of the Flavoenzyme Lactate Oxidase" @default.
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- W1537541495 doi "https://doi.org/10.1016/s0021-9258(19)43359-0" @default.
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