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. 1997 Nov;63(11):4216–4222. doi: 10.1128/aem.63.11.4216-4222.1997

Biodegradation of the gasoline oxygenates methyl tert-butyl ether, ethyl tert-butyl ether, and tert-amyl methyl ether by propane-oxidizing bacteria.

R J Steffan 1, K McClay 1, S Vainberg 1, C W Condee 1, D Zhang 1
PMCID: PMC168740  PMID: 9361407

Abstract

Several propane-oxidizing bacteria were tested for their ability to degrade gasoline oxygenates, including methyl tert-butyl ether (MTBE), ethyl tert-butyl ether (ETBE), and tert-amyl methyl ether (TAME). Both a laboratory strain and natural isolates were able to degrade each compound after growth on propane. When propane-grown strain ENV425 was incubated with 20 mg of uniformly labeled [14C]MTBE per liter, the strain converted > 60% of the added MTBE to 14CO2 in < 30 h. The initial oxidation of MTBE and ETBE resulted in the production of nearly stoichiometric amounts of tert-butyl alcohol (TBA), while the initial oxidation of TAME resulted in the production of tert-amyl alcohol. The methoxy methyl group of MTBE was oxidized to formaldehyde and ultimately to CO2. TBA was further oxidized to 2-methyl-2-hydroxy-1-propanol and then 2-hydroxy isobutyric acid; however, neither of these degradation products was an effective growth substrate for the propane oxidizers. Analysis of cell extracts of ENV425 and experiments with enzyme inhibitors implicated a soluble P-450 enzyme in the oxidation of both MTBE and TBA. MTBE was oxidized to TBA by camphor-grown Pseudomonas putida CAM, which produces the well-characterized P-450cam, but not by Rhodococcus rhodochrous 116, which produces two P-450 enzymes. Rates of MTBE degradation by propane-oxidizing strains ranged from 3.9 to 9.2 nmol/min/mg of cell protein at 28 degrees C, whereas TBA was oxidized at a rate of only 1.8 to 2.4 nmol/min/mg of cell protein at the same temperature.

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Selected References

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  1. Brady J. F., Xiao F., Ning S. M., Yang C. S. Metabolism of methyl tertiary-butyl ether by rat hepatic microsomes. Arch Toxicol. 1990;64(2):157–160. doi: 10.1007/BF01974403. [DOI] [PubMed] [Google Scholar]
  2. Guengerich F. P., MacDonald T. L. Mechanisms of cytochrome P-450 catalysis. FASEB J. 1990 May;4(8):2453–2459. doi: 10.1096/fasebj.4.8.2185971. [DOI] [PubMed] [Google Scholar]
  3. Hardison L. K., Curry S. S., Ciuffetti L. M., Hyman M. R. Metabolism of Diethyl Ether and Cometabolism of Methyl tert-Butyl Ether by a Filamentous Fungus, a Graphium sp. Appl Environ Microbiol. 1997 Aug;63(8):3059–3067. doi: 10.1128/aem.63.8.3059-3067.1997. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Hareland W. A., Crawford R. L., Chapman P. J., Dagley S. Metabolic function and properties of 4-hydroxyphenylacetic acid 1-hydroxylase from Pseudomonas acidovorans. J Bacteriol. 1975 Jan;121(1):272–285. doi: 10.1128/jb.121.1.272-285.1975. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Karlson U., Dwyer D. F., Hooper S. W., Moore E. R., Timmis K. N., Eltis L. D. Two independently regulated cytochromes P-450 in a Rhodococcus rhodochrous strain that degrades 2-ethoxyphenol and 4-methoxybenzoate. J Bacteriol. 1993 Mar;175(5):1467–1474. doi: 10.1128/jb.175.5.1467-1474.1993. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Marinucci A. C., Bartha R. Apparatus for monitoring the mineralization of volatile C-labeled compounds. Appl Environ Microbiol. 1979 Nov;38(5):1020–1022. doi: 10.1128/aem.38.5.1020-1022.1979. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Mo K., Lora C. O., Wanken A. E., Javanmardian M., Yang X., Kulpa C. F. Biodegradation of methyl t-butyl ether by pure bacterial cultures. Appl Microbiol Biotechnol. 1997 Jan;47(1):69–72. doi: 10.1007/s002530050890. [DOI] [PubMed] [Google Scholar]
  8. OMURA T., SATO R. THE CARBON MONOXIDE-BINDING PIGMENT OF LIVER MICROSOMES. I. EVIDENCE FOR ITS HEMOPROTEIN NATURE. J Biol Chem. 1964 Jul;239:2370–2378. [PubMed] [Google Scholar]
  9. Ortiz de Montellano P. R., Mathews J. M. Autocatalytic alkylation of the cytochrome P-450 prosthetic haem group by 1-aminobenzotriazole. Isolation of an NN-bridged benzyne-protoporphyrin IX adduct. Biochem J. 1981 Jun 1;195(3):761–764. doi: 10.1042/bj1950761. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Perry J. J. Substrate specificity in hydrocarbon utilizing microorganisms. Antonie Van Leeuwenhoek. 1968;34(1):27–36. doi: 10.1007/BF02046411. [DOI] [PubMed] [Google Scholar]
  11. Salanitro J. P., Diaz L. A., Williams M. P., Wisniewski H. L. Isolation of a Bacterial Culture That Degrades Methyl t-Butyl Ether. Appl Environ Microbiol. 1994 Jul;60(7):2593–2596. doi: 10.1128/aem.60.7.2593-2596.1994. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Unger B. P., Gunsalus I. C., Sligar S. G. Nucleotide sequence of the Pseudomonas putida cytochrome P-450cam gene and its expression in Escherichia coli. J Biol Chem. 1986 Jan 25;261(3):1158–1163. [PubMed] [Google Scholar]
  13. Wackett L. P., Brusseau G. A., Householder S. R., Hanson R. S. Survey of microbial oxygenases: trichloroethylene degradation by propane-oxidizing bacteria. Appl Environ Microbiol. 1989 Nov;55(11):2960–2964. doi: 10.1128/aem.55.11.2960-2964.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Whited G. M., Gibson D. T. Separation and partial characterization of the enzymes of the toluene-4-monooxygenase catabolic pathway in Pseudomonas mendocina KR1. J Bacteriol. 1991 May;173(9):3017–3020. doi: 10.1128/jb.173.9.3017-3020.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]

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