Skip to main content
Applied and Environmental Microbiology logoLink to Applied and Environmental Microbiology
. 1991 Aug;57(8):2131–2134. doi: 10.1128/aem.57.8.2131-2134.1991

Carboxylation of o-cresol by an anaerobic consortium under methanogenic conditions.

J G Bisaillon 1, F Lépine 1, R Beaudet 1, M Sylvestre 1
PMCID: PMC183539  PMID: 1768084

Abstract

The metabolism of o-cresol under methanogenic conditions by an anaerobic consortium known to carboxylate phenol to benzoate was investigated. After incubation with the consortium at 29 degrees C for 59 days, o-cresol was transformed to 3-methylbenzoic acid, which was not further metabolized by the consortium. Proteose peptone in the culture medium was essential for the transformation of o-cresol. In addition, a transient compound detected in the culture was identified as 4-hydroxy-3-methylbenzoic acid. o-Cresol-6d was transformed by the consortium to deuterated hydroxy-methylbenzoic acid and deuterated methylbenzoic acid. These results demonstrate that o-cresol is carboxylated in the para position relative to the phenolic hydroxyl group and dehydroxylated by the anaerobic consortium.

Full text

PDF
2133

Selected References

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

  1. Berry D. F., Francis A. J., Bollag J. M. Microbial metabolism of homocyclic and heterocyclic aromatic compounds under anaerobic conditions. Microbiol Rev. 1987 Mar;51(1):43–59. doi: 10.1128/mr.51.1.43-59.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Boyd S. A., Shelton D. R., Berry D., Tiedje J. M. Anaerobic biodegradation of phenolic compounds in digested sludge. Appl Environ Microbiol. 1983 Jul;46(1):50–54. doi: 10.1128/aem.46.1.50-54.1983. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Evans W. C., Fuchs G. Anaerobic degradation of aromatic compounds. Annu Rev Microbiol. 1988;42:289–317. doi: 10.1146/annurev.mi.42.100188.001445. [DOI] [PubMed] [Google Scholar]
  4. Genthner B. R., Townsend G. T., Chapman P. J. Anaerobic transformation of phenol to benzoate via para-carboxylation: use of fluorinated analogues to elucidate the mechanism of transformation. Biochem Biophys Res Commun. 1989 Aug 15;162(3):945–951. doi: 10.1016/0006-291x(89)90764-x. [DOI] [PubMed] [Google Scholar]
  5. 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]
  6. 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]
  7. Roberts D. J., Fedorak P. M., Hrudey S. E. CO(2) Incorporation and 4-Hydroxy-2-Methylbenzoic Acid Formation during Anaerobic Metabolism of m-Cresol by a Methanogenic Consortium. Appl Environ Microbiol. 1990 Feb;56(2):472–478. doi: 10.1128/aem.56.2.472-478.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Smolenski W. J., Suflita J. M. Biodegradation of cresol isomers in anoxic aquifers. Appl Environ Microbiol. 1987 Apr;53(4):710–716. doi: 10.1128/aem.53.4.710-716.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Wang Y. T., Suidan M. T., Pfeffer J. T., Najm I. Effects of some alkyl phenols on methanogenic degradation of phenol. Appl Environ Microbiol. 1988 May;54(5):1277–1279. doi: 10.1128/aem.54.5.1277-1279.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]

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

RESOURCES