Biosynthesis of a Cyclic Tautomer1of (3-Methylmaleyl)acetone from 4-Hydroxy-3,5-dimethylbenzoate byPseudomonassp. HH35 but Not byRhodococcus rhodochrousN75 |
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| Institution: | 1. Department of Genetics, Ribeirão Preto Medical School, University of São Paulo, Ribeirão Preto, SP, 14049-900, Brazil;2. Department of Biochemistry and Immunology, Ribeirão Preto Medical School, University of São Paulo, Ribeirão Preto, SP, 14049-900, Brazil;3. Department of Physiological Sciences, Health Sciences Centre, Federal University of Espirito Santo, Vitória, ES, 29047-105, Brazil;4. Department of Biochemistry and Tissue Biology, Institute of Biology, University of Campinas (UNICAMP), Campinas, SP, 13083-970, Brazil;5. Systems and Synthetic Biology Laboratory, Department of Cell and Molecular Biology, Ribeirão Preto Medical School, University of São Paulo, Ribeirão Preto, 14049-900, Brazil |
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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. |
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