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Studies on the enzymic decomposition of urocanic acid. V. The formation of 4-oxoglutaramic acid, a nonenzymic oxidation product of 4 - imidazoione -5 -propionic acid



Studies on the enzymic decomposition of urocanic acid. V. The formation of 4-oxoglutaramic acid, a nonenzymic oxidation product of 4 - imidazoione -5 -propionic acid



Jour Biol Chem 238(4): 1423-1431



4-Oxoglutaramic acid has been identified as the primary product of the dye reduction reaction occurring in solutions containing urocanate and urocanase. The amide arises by the nonenzymic oxidation of 4(5)-imidazolone-5(4)[long dash]propionic acid with the dye as the hydrogen acceptor. The oxidation also occurs aerobically in the absence of any added hydrogen acceptor under conditions of slightly acid or neutral pH and, to a lesser extent, in alkali. It is probable that the oxygen uptake, previously observed during the spontaneous decomposition of imidazolo-nepropionic acid, and thought to be involved in the formation of formyliso-glutamine, is in fact accounted for by the oxidation to 4-oxoglutaramic acid. Although alkaline pH favors the preferential formation of for-mylisoglutamine, the reaction is probably a simple hydrolysis. Other products of the oxidation reaction, in addition to 4-oxoglutaramic acid, are ammonia and formic acid. The latter arises from carbon 2 of the imidazoione ring of imidazolonepropionic acid. 4-Oxoglutaramic acid has been isolated by the use of Dowex-1-acetate chromatography and the 2, 4-dinitrophenylhydrazone, phenylhydrazone and semicarbazone characterized.

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