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Appl Environ Microbiol. 1991 March; 57(3): 820-824
Copyright © 1991, American Society for Microbiology. All Rights Reserved.

Influence of Substituents on Reductive Dehalogenation of 3-Chlorobenzoate Analogs

Jan Dolfing and James M. Tiedje^*

Department of Crop and Soil Sciences and Department of Microbiology and Public Health, Michigan State University, East Lansing, Michigan 48824

ABSTRACT

The biochemical effects of aryl substituents on the reductive dechlorination of 3-chlorobenzoate analogs were quantified with (i) a stable 3-chlorobenzoate-grown methanogenic sludge enrichment, (ii) Desulfomonile tiedjei DCB-1, isolated from this enrichment and able to catalyze the reductive dechlorination of 3-chlorobenzoate, and (iii) a defined 3-chlorobenzoate-degrading methanogenic consortium with D. tiedjei as the key dechlorinating organism. The addition of hydrogen stimulated the dechlorination rate in the consortium. The extent of this stimulation depended on the substituent. The data were evaluated with various sets of substituent constants compiled for the Hammett equation. None of the sets yielded a satisfactory correlation between experimental values and theoretical constants. This suggests that the microbially catalyzed reductive dechlorination of 3-chlorobenzoate cannot be described simply as either a nucleophilic or an electrophilic substitution reaction. Nevertheless, observations that the presence of a para-amino or -hydroxy group inhibited the rate of dechlorination suggest that the rate-limiting step in the reductive dechlorination of 3-chlorobenzoate is a nucleophilic attack on the negatively charged electron cloud around the benzene nucleus.

^* Corresponding author.

Present address: Department of Biochemistry, Groningen Biotechnology Center, University of Groningen, Nijenborgh 16, NL-9747 AG Groningen, The Netherlands.

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