Skip to main content
NCBI home page
Applied and Environmental Microbiology logoLink to Applied and Environmental Microbiology
. 1992 Feb;58(2):496–501. doi: 10.1128/aem.58.2.496-501.1992

Metabolites formed during anaerobic transformation of toluene and o-xylene and their proposed relationship to the initial steps of toluene mineralization.

P J Evans 1, W Ling 1, B Goldschmidt 1, E R Ritter 1, L Y Young 1
PMCID: PMC195274  PMID: 1610173

Abstract

Strain T1 is a facultative bacterium that is capable of anaerobic toluene degradation under denitrifying conditions. While 80% of the carbon from toluene is either oxidized to carbon dioxide or assimilated into cellular carbon, a significant portion of the remainder is transformed into two dead-end metabolites. These metabolites were produced simultaneous to the mineralization of toluene and were identified as benzylsuccinic acid and benzylfumaric acid. Identification was based on comparison of mass spectra of the methyl esters of the metabolites and authentic compounds that were chemically synthesized. Strain T1 is also capable of o-xylene transformation during growth on toluene. o-Xylene does not serve as a source of carbon and is not mineralized. Rather, it is transformed to analogous dead-end metabolites, (2-methylbenzyl)-succinic acid and (2-methylbenzyl)-fumaric acid. o-Xylene transformation also occurred during growth on succinic acid, which suggests that attack of the methyl group by succinyl-coenzyme A is a key reaction in this transformation. We reason that the main pathway for toluene oxidation to carbon dioxide involves a mechanism similar to that for the formation of the metabolites and involves an attack of the methyl group of toluene by acetyl-coenzyme A.

Full text

PDF
496

Selected References

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

  1. Altenschmidt U., Fuchs G. Anaerobic degradation of toluene in denitrifying Pseudomonas sp.: indication for toluene methylhydroxylation and benzoyl-CoA as central aromatic intermediate. Arch Microbiol. 1991;156(2):152–158. doi: 10.1007/BF00290990. [DOI] [PubMed] [Google Scholar]
  2. Baggi G., Barbieri P., Galli E., Tollari S. Isolation of a Pseudomonas stutzeri strain that degrades o-xylene. Appl Environ Microbiol. 1987 Sep;53(9):2129–2132. doi: 10.1128/aem.53.9.2129-2132.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Cohen S. G., Milovanović A. Absolute steric course of hydrolysis by alpha-chymotrypsin. Esters of alpha-benzylsuccinic, alpha-methyl-beta-phenylpropionic, and alpha-methylsuccinic acids. J Am Chem Soc. 1968 Jun 19;90(13):3495–3502. doi: 10.1021/ja01015a036. [DOI] [PubMed] [Google Scholar]
  4. Dolfing J., Zeyer J., Binder-Eicher P., Schwarzenbach R. P. Isolation and characterization of a bacterium that mineralizes toluene in the absence of molecular oxygen. Arch Microbiol. 1990;154(4):336–341. doi: 10.1007/BF00276528. [DOI] [PubMed] [Google Scholar]
  5. Evans P. J., Mang D. T., Kim K. S., Young L. Y. Anaerobic degradation of toluene by a denitrifying bacterium. Appl Environ Microbiol. 1991 Apr;57(4):1139–1145. doi: 10.1128/aem.57.4.1139-1145.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Evans P. J., Mang D. T., Young L. Y. Degradation of toluene and m-xylene and transformation of o-xylene by denitrifying enrichment cultures. Appl Environ Microbiol. 1991 Feb;57(2):450–454. doi: 10.1128/aem.57.2.450-454.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Grbić-Galić D., Vogel T. M. Transformation of toluene and benzene by mixed methanogenic cultures. Appl Environ Microbiol. 1987 Feb;53(2):254–260. doi: 10.1128/aem.53.2.254-260.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Harwood C. S., Gibson J. Uptake of benzoate by Rhodopseudomonas palustris grown anaerobically in light. J Bacteriol. 1986 Feb;165(2):504–509. doi: 10.1128/jb.165.2.504-509.1986. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Kuhn E. P., Zeyer J., Eicher P., Schwarzenbach R. P. Anaerobic degradation of alkylated benzenes in denitrifying laboratory aquifer columns. Appl Environ Microbiol. 1988 Feb;54(2):490–496. doi: 10.1128/aem.54.2.490-496.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Lovley D. R., Lonergan D. J. Anaerobic Oxidation of Toluene, Phenol, and p-Cresol by the Dissimilatory Iron-Reducing Organism, GS-15. Appl Environ Microbiol. 1990 Jun;56(6):1858–1864. doi: 10.1128/aem.56.6.1858-1864.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Williams R. J., Evans W. C. The metabolism of benzoate by Moraxella species through anaerobic nitrate respiration. Evidence for a reductive pathway. Biochem J. 1975 Apr;148(1):1–10. doi: 10.1042/bj1480001a. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Applied and Environmental Microbiology are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES