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. 1991 Apr;57(4):932–940. doi: 10.1128/aem.57.4.932-940.1991

Aerobic Microbial Cometabolism of Benzothiophene and 3-Methylbenzothiophene

Phillip M Fedorak 1,*, Dunja Grbić-Galić 1
PMCID: PMC182825  PMID: 16348471

Abstract

A culture enriched by growth on 1-methylnaphthalene was used to study the aerobic biotransformations of benzothiophene and 3-methylbenzothiophene. Neither of the sulfur heterocyclic compounds would support growth, but they were transformed by the culture growing on 1-methylnaphthalene or glucose or peptone. Cometabolism of benzothiophene yielded benzothiophene-2,3-dione, whereas that of 3-methylbenzothiophene yielded 3-methylbenzothiophene sulfoxide and the corresponding sulfone. The identities of the dione and sulfone were verified by comparison with authentic standards. The identity of the sulfoxide was surmised from gas chromatography-mass spectrometry and gas chromatography- Fourier transform infrared spectroscopy results. Oxidation preferentially occurred at carbons 2 and 3 in benzothiophene, but when carbon 3 was substituted with a methyl group, as in 3-methylbenzothiophene, the sulfur atom was oxygenated. The predominant microorganism in the enrichment culture was a Pseudomonas strain, designated BT1, which mineralized aromatic but not aliphatic hydrocarbons. This isolate cometabolized benzothiophene and 3-methylbenzothiophene. There was no evidence that it could metabolize 3-methylbenzothiophene sulfone. When 3-methylbenzothiophene was added to Prudhoe Bay crude oil, the sulfur heterocycle was oxidized to its sulfoxide and sulfone by strain BT1 as it grew on the aromatic hydrocarbons in the crude oil. Benzothiophene-2,3-dione was found to be chemically unstable when incubated with Prudhoe Bay crude oil. Thus its formation from benzothiophene in the presence of crude oil could not be determined.

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Selected References

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  1. Atlas R. M. Microbial degradation of petroleum hydrocarbons: an environmental perspective. Microbiol Rev. 1981 Mar;45(1):180–209. doi: 10.1128/mr.45.1.180-209.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Bohonos N., Chou T. W., Spanggord R. J. Some observations on biodegradation of pollutants in aquatic systems. Jpn J Antibiot. 1977 Dec;30 (Suppl):275–285. [PubMed] [Google Scholar]
  3. Dalton H., Stirling D. I. Co-metabolism. Philos Trans R Soc Lond B Biol Sci. 1982 Jun 11;297(1088):481–496. doi: 10.1098/rstb.1982.0056. [DOI] [PubMed] [Google Scholar]
  4. Fedorak P. M., Payzant J. D., Montgomery D. S., Westlake D. W. Microbial degradation of n-alkyl tetrahydrothiophenes found in petroleum. Appl Environ Microbiol. 1988 May;54(5):1243–1248. doi: 10.1128/aem.54.5.1243-1248.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Fedorak P. M., Westlake D. W. Fungal Metabolism of n-Alkylbenzenes. Appl Environ Microbiol. 1986 Feb;51(2):435–437. doi: 10.1128/aem.51.2.435-437.1986. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Fedorak P. M., Westlake D. W. Microbial degradation of alkyl carbazoles in Norman wells crude oil. Appl Environ Microbiol. 1984 Apr;47(4):858–862. doi: 10.1128/aem.47.4.858-862.1984. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Foght J. M., Fedorak P. M., Westlake D. W. Mineralization of [14C]hexadecane and [14C]phenanthrene in crude oil: specificity among bacterial isolates. Can J Microbiol. 1990 Mar;36(3):169–175. doi: 10.1139/m90-030. [DOI] [PubMed] [Google Scholar]
  8. Foght J. M., Westlake D. W. Degradation of polycyclic aromatic hydrocarbons and aromatic heterocycles by a Pseudomonas species. Can J Microbiol. 1988 Oct;34(10):1135–1141. doi: 10.1139/m88-200. [DOI] [PubMed] [Google Scholar]
  9. Fujioka M., Wada H. The bacterial oxidation of indole. Biochim Biophys Acta. 1968 Apr 16;158(1):70–78. doi: 10.1016/0304-4165(68)90073-1. [DOI] [PubMed] [Google Scholar]
  10. Jacob J., Schmoldt A., Grimmer G. The predominant role of S-oxidation in rat liver metabolism of thiaarenes. Cancer Lett. 1986 Jul;32(1):107–116. doi: 10.1016/0304-3835(86)90045-5. [DOI] [PubMed] [Google Scholar]
  11. Jamison V. W., Raymond R. L., Hudson J. O. Microbial Hydrocarbon Co-oxidation. III. Isolation and Characterization of an alpha, alpha'-Dimethyl-cis, cis-Muconic Acid-producing Strain of Nocardia corallina. Appl Microbiol. 1969 Jun;17(6):853–856. doi: 10.1128/am.17.6.853-856.1969. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Laborde A. L., Gibson D. T. Metabolism of dibenzothiophene by a Beijerinckia species. Appl Environ Microbiol. 1977 Dec;34(6):783–790. doi: 10.1128/aem.34.6.783-790.1977. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Mormile M. R., Atlas R. M. Mineralization of the dibenzothiophene biodegradation products 3-hydroxy-2-formyl benzothiophene and dibenzothiophene sulfone. Appl Environ Microbiol. 1988 Dec;54(12):3183–3184. doi: 10.1128/aem.54.12.3183-3184.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Sagardía F., Rigau J. J., Martínez-Lahoz A., Fuentes F., López C., Flores W. Degradation of benzothiophene and related compounds by a soil Pseudomonas in an oil-aqueous environment. Appl Microbiol. 1975 Jun;29(6):722–725. doi: 10.1128/am.29.6.722-725.1975. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Wackett L. P., Kwart L. D., Gibson D. T. Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putida. Biochemistry. 1988 Feb 23;27(4):1360–1367. doi: 10.1021/bi00404a041. [DOI] [PubMed] [Google Scholar]
  16. Williams P. A., Catterall F. A., Murray K. Metabolism of naphthalene, 2-methylnaphthalene, salicylate, and benzoate by Pseudomonas PG: regulation of tangential pathways. J Bacteriol. 1975 Nov;124(2):679–685. doi: 10.1128/jb.124.2.679-685.1975. [DOI] [PMC free article] [PubMed] [Google Scholar]

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