= Malic acid
{title2=$\mathrm C_4\mathrm H_6\mathrm O_5$}
{wiki}
<Malic acid> is a four-carbon dicarboxylic <acid> with one <hydroxyl group>. Its deprotonated form, <malate>, is an intermediate of the <citric acid cycle>.
Oxidation of <malate> to <oxaloacetate> couples a change in the carbon skeleton's functional groups to reduction of <NAD+>. The reaction illustrates why protonation state and oxidation state are separate aspects of a metabolite's identity.<The citric acid cycle by Hans Adolf Krebs>[Table 1, malic and oxaloacetic acids]{ref}
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