This Article
Right arrow Full Text
Right arrow Full Text (PDF)
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Services
Right arrow Similar articles in this journal
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Download to citation manager
Right arrowReprints and Permissions
Right arrow Copyright Information
Right arrow Books from ASM Press
Right arrow MicrobeWorld
Citing Articles
Right arrow Citing Articles via HighWire
Right arrow Citing Articles via Google Scholar
Google Scholar
Right arrow Articles by Kropp, K. G.
Right arrow Articles by Suflita, J. M.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Kropp, K. G.
Right arrow Articles by Suflita, J. M.
Agricola
Right arrow Articles by Kropp, K. G.
Right arrow Articles by Suflita, J. M.

 Previous Article  |  Next Article 

Applied and Environmental Microbiology, December 2000, p. 5393-5398, Vol. 66, No. 12
0099-2240/00/$04.00+0
Copyright © 2000, American Society for Microbiology. All rights reserved.

Anaerobic Oxidation of n-Dodecane by an Addition Reaction in a Sulfate-Reducing Bacterial Enrichment Culture

Kevin G. Kropp, Irene A. Davidova, and Joseph M. Suflita*

Institute for Energy and the Environment and Department of Botany and Microbiology, University of Oklahoma, Norman, Oklahoma 73019

Received 14 June 2000/Accepted 2 October 2000

We identified trace metabolites produced during the anaerobic biodegradation of H26- and D26-n-dodecane by an enrichment culture that mineralizes these compounds in a sulfate-dependent fashion. The metabolites are dodecylsuccinic acids that, in the case of the perdeuterated substrate, retain all of the deuterium atoms. The deuterium retention and the gas chromatography-mass spectrometry fragmentation patterns of the derivatized metabolites suggest that they are formed by C---H or C---D addition across the double bond of fumarate. As trimethylsilyl esters, two nearly coeluting metabolites of equal abundance with nearly identical mass spectra were detected from each of H26- and D26-dodecane, but as methyl esters, only a single metabolite peak was detected for each parent substrate. An authentic standard of protonated n-dodecylsuccinic acid that was synthesized and derivatized by the two methods had the same fragmentation patterns as the metabolites of H26-dodecane. However, the standard gave only a single peak for each ester type and gas chromatographic retention times different from those of the derivatized metabolites. This suggests that the succinyl moiety in the dodecylsuccinic acid metabolites is attached not at the terminal methyl group of the alkane but at a subterminal position. The detection of two equally abundant trimethylsilyl-esterified metabolites in culture extracts suggests that the analysis is resolving diastereomers which have the succinyl moiety located at the same subterminal carbon in two different absolute configurations. Alternatively, there may be more than one methylene group in the alkane that undergoes the proposed fumarate addition reaction, giving at least two structural isomers in equal amounts.

* Corresponding author. Mailing address: Department of Botany and Microbiology, Institute for Energy and the Environment, University of Oklahoma, 770 Van Vleet Oval, Room 135, Norman, OK 73019-6131. Phone: (405) 325-5761. Fax: (405) 325-7541. E-mail: jsuflita{at}ou.edu.

Applied and Environmental Microbiology, December 2000, p. 5393-5398, Vol. 66, No. 12
0099-2240/00/$04.00+0
Copyright © 2000, American Society for Microbiology. All rights reserved.


This article has been cited by other articles:

  • Callaghan, A. V., Tierney, M., Phelps, C. D., Young, L. Y. (2009). Anaerobic Biodegradation of n-Hexadecane by a Nitrate-Reducing Consortium. Appl. Environ. Microbiol. 75: 1339-1344 [Abstract] [Full Text]  
  • Davidova, I. A., Duncan, K. E., Choi, O. K., Suflita, J. M. (2006). Desulfoglaeba alkanexedens gen. nov., sp. nov., an n-alkane-degrading, sulfate-reducing bacterium. Int. J. Syst. Evol. Microbiol. 56: 2737-2742 [Abstract] [Full Text]  
  • Callaghan, A. V., Gieg, L. M., Kropp, K. G., Suflita, J. M., Young, L. Y. (2006). Comparison of Mechanisms of Alkane Metabolism under Sulfate-Reducing Conditions among Two Bacterial Isolates and a Bacterial Consortium.. Appl. Environ. Microbiol. 72: 4274-4282 [Abstract] [Full Text]  
  • Davidova, I. A., Gieg, L. M., Nanny, M., Kropp, K. G., Suflita, J. M. (2005). Stable Isotopic Studies of n-Alkane Metabolism by a Sulfate-Reducing Bacterial Enrichment Culture. Appl. Environ. Microbiol. 71: 8174-8182 [Abstract] [Full Text]  
  • Cravo-Laureau, C., Grossi, V., Raphel, D., Matheron, R., Hirschler-Rea, A. (2005). Anaerobic n-Alkane Metabolism by a Sulfate-Reducing Bacterium, Desulfatibacillum aliphaticivorans Strain CV2803T. Appl. Environ. Microbiol. 71: 3458-3467 [Abstract] [Full Text]  
  • Bekins, B. A., Hostettler, F. D., Herkelrath, W. N., Delin, G. N., Warren, E., Essaid, H. I. (2005). Progression of methanogenic degradation of crude oil in the subsurface. Environmental Geosciences 12: 139-152 [Abstract] [Full Text]  
  • Cravo-Laureau, C., Matheron, R., Cayol, J.-L., Joulian, C., Hirschler-Rea, A. (2004). Desulfatibacillum aliphaticivorans gen. nov., sp. nov., an n-alkane- and n-alkene-degrading, sulfate-reducing bacterium. Int. J. Syst. Evol. Microbiol. 54: 77-83 [Abstract] [Full Text]  
  • Van Hamme, J. D., Singh, A., Ward, O. P. (2003). Recent Advances in Petroleum Microbiology. Microbiol. Mol. Biol. Rev. 67: 503-549 [Abstract] [Full Text]  
  • So, C. M., Phelps, C. D., Young, L. Y. (2003). Anaerobic Transformation of Alkanes to Fatty Acids by a Sulfate-Reducing Bacterium, Strain Hxd3. Appl. Environ. Microbiol. 69: 3892-3900 [Abstract] [Full Text]  
  • 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. Appl. Environ. Microbiol. 69: 434-443 [Abstract] [Full Text]  
  • Parales, R. E., Bruce, N. C., Schmid, A., Wackett, L. P. (2002). Biodegradation, Biotransformation, and Biocatalysis (B3). Appl. Environ. Microbiol. 68: 4699-4709 [Full Text]  
  • Achong, G. R., Rodriguez, A. M., Spormann, A. M. (2001). Benzylsuccinate Synthase of Azoarcus sp. Strain T: Cloning, Sequencing, Transcriptional Organization, and Its Role in Anaerobic Toluene and m-Xylene Mineralization. J. Bacteriol. 183: 6763-6770 [Abstract] [Full Text]  


Copyright © 2009 by the American Society for Microbiology.   For an alternate route to Journals.ASM.org, visit: http://intl-journals.asm.org | More Info»