Formation of n-alkane- and cycloalkane-derived organic acids during anaerobic growth of a denitrifying bacterium with crude oil

Organic Geochemistry

Volumn 34, Issue 9, 2003, Pages 1313-1323

  Wilkes, Heinz ^a   Kühner, Simon ^b   Bolm, Carsten ^c   Fischer, Thomas ^d   Classen, Arno ^c   Widdel, Friedrich ^b   Rabus, Ralf ^b  

^a GFZ GERMAN RESEARCH CENTRE FOR GEOSCIENCES   (Germany)

^b MAX PLANCK INSTITUTE FOR MARINE MICROBIOLOGY   (Germany)

^c RWTH AACHEN UNIVERSITY   (Germany)

^d FORSCHUNGSZENTRUM JÜLICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ACTIVATION; CRUDE PETROLEUM; ORGANIC ACIDS;

BACTERIUM;

PARAFFINS;

ALKANE; ANAEROBIOSIS; BIODEGRADATION; CRUDE OIL; GEOCHEMISTRY; HYDROCARBON; METABOLITE; NITRIFYING BACTERIUM;

AZOARCUS;

EID: 0042859855     PISSN: 01466380     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0146-6380(03)00099-8     Document Type: Article

References (38)

1. 2 by a new type of sulfate-reducing bacterium. Archives of Microbiology 156, 5-14.
2. Aeckersberg, F., Rainey, F.A., Widdel, F., 1998. Growth, natural relationships, cellular fatty acids and metabolic adaptation of sulfate-reducing bacteria that utilize long-chain alkanes under anoxic conditions. Archives of Microbiology 170, 361-369.
3. Anderson, R., Lovley, D., 2000. Hexadecane decay by methanogenesis. Nature 404, 722-723.
4. Beller, H.R., 2000. Metabolic indicators for detecting in situ anaerobic alkylbenzene degradation. Biodegradation 11, 125-139.
5. Beller, H.R., Spormann, A., 1999. Substrate range of benzylsuccinate synthase from Azoarcus strain T. FEMS Microbiology Letters 178, 147-153.
6. Biegert, T., Fuchs, G., 1995. Anaerobic oxidation of toluene (analogues) to benzoate (analogues) by whole cells and by cell extracts of a denitrifying Thauera sp. Archives of Microbiology 163, 407-417.
7. Bregnard, T.A., Häner, A., Höhener, P., Zeyer, J., 1997. Degradation of pristane in nitrate-reducing microcosms and enrichment cultures. Applied and Environmental Microbiology 63, 2077-2081.
8. Caldwell, M., Garrett, R., Prince, R., Suflita, J., 1998. Anaerobic biodegradation of long-chain n-alkanes under sulfate-reducing conditions. Environmental Science and Technology 32, 2191-2195.
9. Connan, J., Lacrampe-Coulome, G., Magot, M., 1996. Origin of gases in reservoirs. In: Dolenc, D. (Ed.), Proceedings of the 1995 International Gas Research Conference. Government Institutes, Rockville, pp. 21-62.
10. Ehrenreich, P., Behrends, A., Harder, J., Widdel, F., 2000. Anaerobic oxidation of alkanes by newly isolated denitrifying bacteria. Archives of Microbiology 173, 58-64.
11. Elshahed, M.S., Gieg, L.M., McInerney, M.J., Suflita, J.M., 2001. Signature metabolites attesting to the in situ attenuation of alkylbenzenes in anaerobic environments. Environmental Science and Technology 35, 632-689.
12. Evans, P.J., Ling, W., Goldschmidt, B., Ritter, E.R., Young, L.Y., 1992. Metabolites formed during anaerobic transformation of toluene and o-xylene and their proposed relationship to the initial steps of toluene mineralization. Applied and Environmental Microbiology 58, 496-501.
13. Gieg, L.M., Suflita, J.M., 2002. Detection of anaerobic metabolites of saturated and aromatic hydrocarbons in petroleum-contaminated aquifers. Environmental Science and Technology 36, 3755-3762.
14. Giese, B., Meister, J., 1977. Die Addition von Kohlenwasserstoffen an Olefine. Eine neue synthetische Methode. Chemische Berichte 110, 2588-2600.
15. Giese, B., Kretzschmar, G., 1982. Radikalische Addition an cyclische Derivate der Maleinsäure. Chemische Berichte 115, 2012-2014.
16. Giese, B., Kretzschmar, G., 1984. Radikalkettenreaktionen mit Maleinsäureanhydriden. Zur kontrathermodynamischen Stereoselektivität. Chemische Berichte 117, 3175-3182.
17. Groh, S., Nelson, M., 1990. Mechanisms of activation of carbon-hydrogen bonds by metalloenzymes. In: Davies, J., Watson, P., Liebman, J., Greenberg, A. (Eds.), Selective Hydrocarbon Activation. VCH, Weinheim, Germany, pp. 305-378.
18. Heider, J., Spormann, A.M., Beller, H.R., Widdel, F., 1999. Anaerobic bacterial metabolism of hydrocarbons. FEMS Microbiology Reviews 22, 459-473.
19. Kropp, K.G., Davidova, I.A., Suflita, J.M., 2000. Anaerobic oxidation of n-dodecane by an addition reaction in a sulfate-reducing bacterial enrichment culture. Applied and Environmental Microbiology 66, 5393-5398.
20. McLafferty, F.W., Stauffer, D.B., 1989. The Wiley/NBS registry of mass spectral data. Wiley, New York.
21. Palmer, S.E., 1993. Effect of biodegradation and water washing on crude oil composition. In: Engel, M.H., Macko, S.A. (Eds.), Organic Geochemistry. Plenum Press, New York, pp. 511-533.
22. Peters, K.E., Moldowan, J.M., 1993. The Biomarker Guide. Prentice Hall, Englewood Cliffs.
23. Rabus, R., Widdel, F., 1995a. Conversion studies with substrate analogues of toluene in a sulfate-reducing bacterium, strain Tol2. Archives of Microbiology 164, 448-451.
24. Rabus, R., Widdel, F., 1995b. Anaerobic degradation of ethylbenzene and other aromatic hydrocarbons by new denitrifying bacteria. Archives of Microbiology 163, 96-103.
25. Rabus, R., Widdel, F., 1996. Utilization of alkylbenzenes during anaerobic growth of pure cultures of denitrifying bacteria on crude oil. Applied and Environmental Microbiology 62, 1238-1241.
26. Rabus, R., Wilkes, H., Schramm, A., Harms, G., Behrends, A., Amann, R., Widdel, F., 1999. Anaerobic degradation of alkylbenzenes and n-alkanes from crude oil in an enrichment culture of denitrifying bacteria affiliating with the β-subclass of Proteobacteria. Environmental Microbiology 1, 145-157.
27. Rabus, R., Wilkes, H., Behrends, A., Armstroff, A., Fischer, T., Pierik, A.J., Widdel, F., 2001. Anaerobic initial reaction of n-alkanes in a denitrifying bacterium: evidence for (1-methylpentyl)succinate as initial product and for involvement of an organic radical in n-hexane metabolism. Journal of Bacteriology 183, 1707-1715.
28. Reusser, D.E., Istok, J.D., Beller, H.R., Field, J.A., 2002. In situ transformation of deuterated toluene and xylene to benzylsuccinic acid analogues in BTEX-contaminated aquifers. Environmental and Science Technology 36, 4127-4134.
29. Rios-Hernandez, L.A., Gieg, L.M., Suflita, J.M., 2003. Biodegradation of an alicyclic hydrocarbon by a sulfate-reducing enrichment from a gas condensate-contaminated aquifer. Applied and Environmental Microbiology 69, 434-443.
30. Rueter, P., Rabus, R., Wilkes, H., Aeckersberg, F., Rainey, F.A., Jannasch, H.W., Widdel, F., 1994. Anaerobic oxidation of hydrocarbons in crude oil by new types of sulphate-reducing bacteria. Nature 372, 455-458.
31. So, C.M., Young, L.Y., 1999a. Isolation and characterization of a sulfate-reducing bacterium that anaerobically degrades alkanes. Applied and Environmental Microbiology 65, 2969-2976.
32. So, C.M., Young, L.Y., 1999b. Initial reactions in anaerobic alkane degradation by a sulfate reducer, strain AK-01. Applied and Environmental Microbiology 65, 5532-5540.
33. Spormann, A.M., Widdel, F., 2000. Metabolism of alkylbenzenes, alkanes and other hydrocarbons in anaerobic bacteria. Biodegradation 11, 85-105.
34. White, R., Coon, M., 1980. Oxygen activation by cytochrome P-450. Annual Review of Biochemistry 49, 315-356.
35. Widdel, F., Rabus, R., 2001. Anaerobic biodegradation of saturated and aromatic hydrocarbons. Current Opinion in Biotechnology 12, 259-276.
36. Wilkes, H., Boreham, C., Harms, G., Zengler, K., Rabus, R., 2000. Anaerobic degradation and carbon isotopic fractionation of alkylbenzenes in crude oil by sulphate-reducing bacteria. Organic Geochemistry 31, 101-115.
37. Wilkes, H., Rabus, R., Fischer, Th., Armstroff, A., Behrends, A., Widdel, F., 2002. Anaerobic degradation of n-alkanes in a denitrifying bacterium: Further degradation of the initial intermediate (1-methylpentyl)succinate via C-skeleton rearrangement. Archives of Microbiology 177, 235-243.
38. Zengler, K., Richnow, H.H., Rosselló-Mora, R., Michaelis, W., Widdel, F., 1999. Methane formation from long-chain alkanes by anaerobic microorganisms. Nature 401, 266-269.