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Applied and Environmental Microbiology, December 1999, p. 5242-5246, Vol. 65, No. 12
0099-2240/99/$04.00+0
Copyright © 1999, American Society for Microbiology. All rights reserved.

cis-Chlorobenzene Dihydrodiol Dehydrogenase (TcbB) from Pseudomonas sp. Strain P51, Expressed in Escherichia coli DH5alpha (pTCB149), Catalyzes Enantioselective Dehydrogenase Reactions

Henning Raschke,dagger Thomas Fleischmann, Jan Roelof Van Der Meer, and Hans-Peter E. Kohler*

Swiss Federal Institute for Environmental Sciences and Technology (EAWAG), CH-8600 Dübendorf, Switzerland

Received 10 May 1999/Accepted 14 September 1999

cis-Chlorobenzene dihydrodiol dehydrogenase (CDD) from Pseudomonas sp. strain P51, cloned into Escherichia coli DH5alpha (pTCB149) was able to oxidize cis-dihydrodihydroxy derivatives (cis-dihydrodiols) of dihydronaphthalene, indene, and four para-substituted toluenes to the corresponding catechols. During the incubation of a nonracemic mixture of cis-1,2-indandiol, only the (+)-cis-(1R,2S) enantiomer was oxidized; the (-)-cis-(S,2R) enantiomer remained unchanged. CDD oxidized both enantiomers of cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene, but oxidation of the (+)-cis-(1S,2R) enantiomer was delayed until the (-)-cis-(1R,2S) enantiomer was completely depleted. When incubated with nonracemic mixtures of para-substituted cis-toluene dihydrodiols, CDD always oxidized the major enantiomer at a higher rate than the minor enantiomer. When incubated with racemic 1-indanol, CDD enantioselectively transformed the (+)-(1S) enantiomer to 1-indanone. This stereoselective transformation shows that CDD also acted as an alcohol dehydrogenase. Additionally, CDD was able to oxidize (+)-cis-(1R,2S)-dihydroxy-1,2-dihydronaphthalene, (+)-cis-monochlorobiphenyl dihydrodiols, and (+)-cis-toluene dihydrodiol to the corresponding catechols.

* Corresponding author. Mailing address: Department of Microbiology, EAWAG, Überlandstrasse 133, CH-8600 Dübendorf, Switzerland. Phone: 41 1 823 5521. Fax: 41 1 823 5547. E-mail: kohler{at}eawag.ch.

dagger Present address: Fichtner, 70191 Stuttgart, Germany.

Applied and Environmental Microbiology, December 1999, p. 5242-5246, Vol. 65, No. 12
0099-2240/99/$04.00+0
Copyright © 1999, American Society for Microbiology. All rights reserved.


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