Skip to main content
SpringerLink
Log in

Metabolism of 2,5-dichlorobenzoic acid inPseudomonas stutzeri

  • Published:
Folia Microbiologica Aims and scope Submit manuscript

Abstract

4-Chroropyrocatechol is formed as a results of the oxidation of 2,5-dichlorobenzoate byPseudomonas stutzeri. 3-Chloro-cis,cis-muconic acid is the product of the oxidation of 4-chloropyrocatechol. Pyrocatechol 1,2-dioxygenase, gentisate 1,2-dioxygenase, but not pyrocatechol 2,3-dioxygenase or protocatechuate 3,4-dioxygenase activities were found in cell-free extracts. Theortho cleavage activity for catechols appeared to involve induction of isoenzymes with different stereospecificity towards chlorocatechols. A catablic pathway for the degradation of 2,5-dichlorobenzoate by a newly isolated strain ofP. stutzeri was proposed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

4-CPC:

4-chloropyrocatechol (13)

2-CBA:

2-chlorobenzoic acid (4)

2-HBA:

2-hydroxybenzoic acid (salicylic acid;2)

2-FBA:

2-fluorobenzoic acid (3)

2,5-DCBA:

2,5-dichlorobenzoic acid (5)

2,5-DHBA:

2,5-dihydroxybenzoic acid (gentisic acid;6)

References

  • Baggi G.: Ricerche sulla degradazione di acidi clorobenzoici.Ann. Microbiol.35, 71–78 (1985).

    CAS  Google Scholar 

  • Crawford R.L., Hutton S.W., Chapman P.J.: Purification and properties of gentisate 1,2-dioxygenase fromMoraxella osloensis.Bacteriol.121, 794–799 (1975).

    CAS  Google Scholar 

  • Dorn E., Knackmuss H.-J.: Chemical structure and biodegradability of halogenated aromatic compounds. Two catechol 1,2-dioxygenases from a 3-chlorobenzoate-grown pseudomonad.Biochem. J.174, 73–84 (1978).

    PubMed  CAS  Google Scholar 

  • Fetzner S., Muller R., Lingens F.: Purification and some properties of 2-halobenzoate 1,2-dioxygenase, a two-component enzyme system frompseudomonas cepacia 2CBS.J. Bacteriol.174, 279–290 (1992).

    PubMed  CAS  Google Scholar 

  • Grishenkov V.G., Fedechkina I.E., Baskunov B.P., Anisimova L.A., Boronin A.M., Golovleva L.A.: Degradation of 3-chlorobenzoic acid by aPseudomonas putida strain.Mikrobiologiya52, 771–776 (1983).

    Google Scholar 

  • Hayaishi O., Katagiri M., Rothberg S.: Studies on oxygenases: Pyrocatechase.J. Biol. Chem.229, 905–920 (1957).

    PubMed  CAS  Google Scholar 

  • Hernandez B.S., Higson, F.K., Kondrat R., Focht D.D.: Metabolism of and inhibition by chlorobenzoates inPseudomonas putida P111.Appl. Environ. Microbiol.57, 3361–3366 (1991).

    PubMed  CAS  Google Scholar 

  • Hickey W., Focht D.D.: Degradation of mono-, di-, and trihalogenated benzoic acids byPseudomonas aeruginosa JB2.Appl. Environ. Microbiol.56, 3842–3852 (1990).

    PubMed  CAS  Google Scholar 

  • Kozlovsky S.A., Zaitsev G.M., Kunc F., Gabriel J., Boronin A.M.: Degradation of 2-chlorobenzoic and 2,5-dichlorobenzoic acids in pure culture byPseudomonas stutzeri.Folia Microbiol.38, 371–375 (1993a).

    CAS  Google Scholar 

  • Kozlovsky S.A., Zaitsev G.M., Kunc F.: Degradation of 2-chlorobenzoic and 2,5-dichlorobenzoic acids in soil columns byPseudomonas stutzeri, Folia Microbiol.38, 376–378 (1993b).

    CAS  Google Scholar 

  • Layne E.: Spectrophotometric and turbidimetric methods for measuring proteins.Methods Enzymol.3, 447–454 (1957).

    Google Scholar 

  • Miguez C.B., Greer C.W., Ingram J.M.: Degradation of mono- and dichlorobenzoic acid isomers by two natural isolates ofAlcaligenes denitrificans.Arch. Microbiol.154, 139–143 (1990).

    Article  PubMed  CAS  Google Scholar 

  • Nozaki M.: Metapyrocatechase (Pseudomonas).Methods Enzymol.17A, 522–525 (1970).

    Article  Google Scholar 

  • Schmidt E., Knackmus H.-J.: Production ofcis, cis-muconate from benzoate and 2-fluor-cis, cis-muconate from 3-fluorobenzoate by 3-chlorobenzoate degrading bacteria.Appl. Microbiol. Biotechnol.20, 351–355 (1984).

    Article  CAS  Google Scholar 

  • Stanier R.Y., Ingraham J.L.: Protocatechuic acid oxidase.J. Biol. Chem..210, 799–808 (1954).

    PubMed  CAS  Google Scholar 

  • Sylvestre M.V., Mailhiot K., Ahmad D., Masse R.: Isolation and preliminary characterization of a 2-chlorobenzoate degradingPseudomonas.Can. J. Microbiol.35, 439–443 (1989).

    Article  PubMed  CAS  Google Scholar 

  • Zaitsev G.M., Baskunov B.P.: Utilization of 3-chlorobenzoic acid byAcinetobacter calcoaceticus.Mikrobiologiya54, 203–208 (1985).

    CAS  Google Scholar 

  • Zaitsev G.M., Karasevich Y.N.: Utilization of 2-chlorobenzoic acid.Mikrobiologiya53, 75–80 (1984).

    CAS  Google Scholar 

  • Zaitsev G.M., Tsitko J.V., Lobanok A.G., Vazhinskaja J.S., Chechenn V.P.: Utilization of halogenated benzenes byRhodococcus rhodochrous.Dokl. AN. Belarussia37, 65–68 (1993).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. UNESCO-ROSTE Course, Institute of Microbiology, Academy of Sciences of the Czech Republic, 142 20, Prague 4, Czech Republic

    S. A. Kozlovsky

  2. Institute of Microbiology, Academy of Sciences of the Belorussia, 220 067, Minsk, Belorussia

    G. M. Zaitsev

  3. Institute of Microbiology, Academy of Sciences of the Czech Republic, 142 20, Prague 4, Czech Republic

    F. Kunc

Authors
  1. S. A. Kozlovsky
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. M. Zaitsev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. F. Kunc
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kozlovsky, S.A., Zaitsev, G.M. & Kunc, F. Metabolism of 2,5-dichlorobenzoic acid inPseudomonas stutzeri . Folia Microbiol 39, 399–403 (1994). https://doi.org/10.1007/BF02814446

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02814446

Keywords

Search

Navigation