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J Bacteriol, June 1998, p. 2849-2853, Vol. 180, No. 11
0021-9193/98/$04.00+0
Copyright © 1998, American Society for Microbiology. All rights reserved.

Distal Cleavage of 3-Chlorocatechol by an Extradiol Dioxygenase to 3-Chloro-2-Hydroxymuconic Semialdehyde

Ulrich Riegert,1 Gesche Heiss,1 Peter Fischer,2 and Andreas Stolz1,*

Institut für Mikrobiologie1 and Institut für Organische Chemie,2 Universität Stuttgart, 70569 Stuttgart, Germany

Received 9 December 1997/Accepted 26 March 1998

A 2,3-dihydroxybiphenyl 1,2-dioxygenase from the naphthalenesulfonate-degrading bacterium Sphingomonas sp. strain BN6 oxidized 3-chlorocatechol to a yellow product with a strongly pH-dependent absorption maximum at 378 nm. A titration curve suggested (de)protonation of an ionizable group with a pKa of 4.4. The product was isolated, purified, and converted, by treatment with diazomethane, to a dimethyl derivative and, by incubation with ammonium chloride, to a picolinic acid derivative. Mass spectra and 1H and 13C nuclear magnetic resonance (NMR) data for these two derivatives prove a 3-chloro-2-hydroxymuconic semialdehyde structure for the metabolite, resulting from distal (1,6) cleavage of 3-chlorocatechol. 3-Methylcatechol and 2,3-dihydroxybiphenyl are oxidized by this enzyme, in contrast, via proximal (2,3) cleavage.

* Corresponding author. Mailing address: Institut für Mikrobiologie der Universität Stuttgart, Allmandring 31, 70569 Stuttgart, Germany. Phone: (0049) (0)711-685-5489. Fax: (0049) (0)711-685-5725. E-mail: andreas.stolz{at}po.uni-stuttgart.de.

J Bacteriol, June 1998, p. 2849-2853, Vol. 180, No. 11
0021-9193/98/$04.00+0
Copyright © 1998, American Society for Microbiology. All rights reserved.


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