The enzymatic cis-trans isomerization of nitrofurans such as 3-(5-nitro-2-furyl)-2-(2-furyl) acrylamide (AF-2) has been proved to occur via the formation of the corresponding nitro anion radicals. Rat liver microsomes supplemented with NADPH exhibited the cis-trans isomerase activity toward AF-2, which is markedly inhibited by p-chloromercuribenzoic acid, but not by carbon monoxide. Purified rat liver NADPH-cytochrome c reductase supplemented with NADPH also exhibited a significant isomerase activity toward the nitrofuran, whereas purified rat liver NADH-cytochrome b5 reductase exhibited only a little activity in the presence of NADPH or NADH. These results indicate that mainly NADPH-cytochrome c reductase is involved in the cis-trans isomerization of nitrofurans, i.e. the formation of nitro anion radicals catalyzed by rat liver microsomes.
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Koga et al. (1984) studied this question.