Biochemical and Biophysical Research Communications 1997-09-08

Biosynthesis of a Cyclic Tautomer1of (3-Methylmaleyl)acetone from 4-Hydroxy-3,5-dimethylbenzoate byPseudomonassp. HH35 but Not byRhodococcus rhodochrousN75

Ronald B. Cain, Peter Fortnagel, Svantje Hebenbrock, Gordon W. Kirby, Hugh J.S. McLenaghan, Ghanakota V. Rao, Stefan Schmidt

Index: Biochem. Biophys. Res. Commun. 238(1) , 197-201, (1997)

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Abstract

Here we report that the bacterial catabolism of 4-hydroxy-3,5-dimethylbenzoic acid 1 takes a different course inRhodococcus rhodochrousN75 andPseudomonassp. strain HH35. The former organism accumulates a degradation metabolite of the acid which we isolated and identified as 2,6-dimethylhydroquinone 2. The latter bacterial strain converts the acid and the hydroquinone into a dead-end metabolite. This novel compound was characterised unequivocally by mass spectrometry and1H and13C NMR and UV spectroscopy as 4-acetonyl-4-hydroxy-2-methylbut-2-en-1,4-olide 4, a cyclic tautomer of (3-methylmaleyl)acetone, which exists as the enol carboxylate form 3 in aqueous solution.