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. 1980 Jan;39(1):68–73. doi: 10.1128/aem.39.1.68-73.1980

Adaptation of Alcaligenes eutrophus B9 and Pseudomonas sp. B13 to 2-Fluorobenzoate as Growth Substrate

K-H Engesser 1, E Schmidt 1, H-J Knackmuss 1
PMCID: PMC291285  PMID: 16345497

Abstract

Alcaligenes eutrophus B9 and Pseudomonas sp. B13 could be adapted to 2-fluorobenzoate as the sole source of carbon and energy. The ability of the A. eutrophus B9 to use this new substrate is clearly based on the defective dihydrodihydroxybenzoate dehydrogenase. Nontoxic 6-fluoro-3,5-cyclohexadiene-1,2-diol-1-carboxylic acid is accumulated instead of 3-fluorocatechol. About 84% of the substrate is dioxygenated to catechol and utilized via the 3-oxoadipate pathway. During continuous adaptation of Pseudomonas sp. B13 regioselectivity of dioxygenation of 2-fluorobenzoate is drastically changed in favor of a 1,2-attack. Consequently, approximately 97% of the substrate is utilized via catechol. A three- to fourfold overproduction of key enzymes of the 3-oxoadipate pathway compensates for the slower turnover rates of the fluorinated substrates.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Bradford M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976 May 7;72:248–254. doi: 10.1016/0003-2697(76)90527-3. [DOI] [PubMed] [Google Scholar]
  2. Clarke K. F., Callely A. G., Livingstone A., Fewson C. A. Metabolism of monofluorobenzoates by Acinetobacter calcoaceticus N.C.I.B. 8250. Formation of monofluorocatechols. Biochim Biophys Acta. 1975 Oct 9;404(2):169–179. doi: 10.1016/0304-4165(75)90323-2. [DOI] [PubMed] [Google Scholar]
  3. Dorn E., Hellwig M., Reineke W., Knackmuss H. J. Isolation and characterization of a 3-chlorobenzoate degrading pseudomonad. Arch Microbiol. 1974;99(1):61–70. doi: 10.1007/BF00696222. [DOI] [PubMed] [Google Scholar]
  4. Dorn E., Knackmuss H. J. Chemical structure and biodegradability of halogenated aromatic compounds. Substituent effects on 1,2-dioxygenation of catechol. Biochem J. 1978 Jul 15;174(1):85–94. doi: 10.1042/bj1740085. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Johnson B. F., Stanier R. Y. Regulation of the -ketoadipate pathway in Alcaligenes eutrophus. J Bacteriol. 1971 Aug;107(2):476–485. doi: 10.1128/jb.107.2.476-485.1971. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Knackmuss H. J., Hellwig M. Utilization and cooxidation of chlorinated phenols by Pseudomonas sp. B 13. Arch Microbiol. 1978 Apr 27;117(1):1–7. doi: 10.1007/BF00689343. [DOI] [PubMed] [Google Scholar]
  7. Ornston L. N., Stanier R. Y. The conversion of catechol and protocatechuate to beta-ketoadipate by Pseudomonas putida. J Biol Chem. 1966 Aug 25;241(16):3776–3786. [PubMed] [Google Scholar]
  8. Ornston L. N. The conversion of catechol and protocatechuate to beta-ketoadipate by Pseudomonas putida. 3. Enzymes of the catechol pathway. J Biol Chem. 1966 Aug 25;241(16):3795–3799. [PubMed] [Google Scholar]
  9. Reineke W., Knackmuss H. J. Chemical structure and biodegradability of halogenate aromatic compounds. Substituent effects on 1,2-dioxygenation of benzoic acid. Biochim Biophys Acta. 1978 Sep 6;542(3):412–423. doi: 10.1016/0304-4165(78)90372-0. [DOI] [PubMed] [Google Scholar]
  10. Reiner A. M. Metabolism of aromatic compounds in bacteria. Purification and properties of the catechol-forming enzyme, 3,5-cyclohexadiene-1,2-diol-1-carboxylic acid (NAD + ) oxidoreductase (decarboxylating). J Biol Chem. 1972 Aug 25;247(16):4960–4965. [PubMed] [Google Scholar]
  11. Rigby P. W., Burleigh B. D., Jr, Hartley B. S. Gene duplication in experimental enzyme evolution. Nature. 1974 Sep 20;251(5472):200–204. doi: 10.1038/251200a0. [DOI] [PubMed] [Google Scholar]
  12. SCHMIDT K., LIAAENJENSEN S., SCHLEGEL H. G. DIE CAROTINOIDE DER THIORHODACEAE. I. OKENON ALS HAUPTEAROTINOID VON CHROMATIUM OKENII PERTY. Arch Mikrobiol. 1963 Aug 1;46:117–126. [PubMed] [Google Scholar]
  13. Schreiber A., Hellwig M., Dorn E., Reineke W., Knackmuss H. J. Critical Reactions in Fluorobenzoic Acid Degradation by Pseudomonas sp. B13. Appl Environ Microbiol. 1980 Jan;39(1):58–67. doi: 10.1128/aem.39.1.58-67.1980. [DOI] [PMC free article] [PubMed] [Google Scholar]

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