Indole-3-pyruvate 2026-11-05
Indole-3-pyruvate is the indole-substituted pyruvate anion named systematically 3-(1H-indol-3-yl)-2-oxopropanoate. It is the conjugate base of indole-3-pyruvic acid. The three-carbon side chain distinguishes it from indole-3-acetate, whose corresponding side chain has two carbons.[ref]
Enzyme Nomenclature by the IUBMB. EC1.14.13.168, substrate and product Glossary.
A biological example is the plant route from tryptophan to the auxin indole-3-acetate. A transamination supplies indole-3-pyruvate; a YUCCA flavin monooxygenase then participates in its conversion to indole-3-acetate. The accepted net reaction uses NADPH and molecular oxygen and releases carbon dioxide, so the step is not simply a change in protonation.[ref]
An original carbon inventory makes the one-carbon loss clear. The indole framework contributes eight carbon atoms, giving eleven in indole-3-pyruvate and ten in indole-3-acetate. Converting 20 nmol of substrate according to the stated reaction distributes nmol of carbon atoms between nmol in the organic product and 20 nmol in carbon dioxide. The balance checks the net stoichiometry, without establishing the provenance of individual oxygen atoms or a reaction rate.