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)

Full Text: HTML

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.

Related Compounds

  • 3,5-Dimethylbenzoi...

Related Articles:

Organotin(IV) based anti-HCV drugs: synthesis, characterization and biochemical activity.

2015-06-14

[Dalton Trans. 44 , 10467-78, (2015)]

Urinary excretion of dimethylhippuric acids in humans after exposure to trimethylbenzenes.

1997-01-01

[Int. Arch. Occup. Environ. Health 69(6) , 491-7, (1997)]

Biological monitoring of experimental human exposure to trimethylbenzene.

1997-06-20

[Sci. Total Environ. 199(1-2) , 73-81, (1997)]

Kinetics of elimination of mesitylene and 3,5-dimethylbenzoic acid after experimental human exposure.

1995-05-01

[Toxicol. Lett. 77(1-3) , 259-64, (1995)]

Metabolism of 3-chloro-, 4-chloro-, and 3,5-dichlorobenzoate by a pseudomonad.

1979-03-01

[Appl. Environ. Microbiol. 37(39) , 421-428., (1979)]

More Articles...