This Article
Right arrow Full Text
Right arrow Full Text (PDF)
Right arrow Supplemental material
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 Schleheck, D.
Right arrow Articles by Cook, A. M.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Schleheck, D.
Right arrow Articles by Cook, A. M.
Agricola
Right arrow Articles by Schleheck, D.
Right arrow Articles by Cook, A. M.

 Previous Article  |  Next Article 

Applied and Environmental Microbiology, August 2007, p. 4725-4732, Vol. 73, No. 15
0099-2240/07/$08.00+0     doi:10.1128/AEM.00632-07
Copyright © 2007, American Society for Microbiology. All Rights Reserved.

Parvibaculum lavamentivorans DS-1T Degrades Centrally Substituted Congeners of Commercial Linear Alkylbenzenesulfonate to Sulfophenyl Carboxylates and Sulfophenyl Dicarboxylates{triangledown} ,{dagger}

David Schleheck,1,2 Thomas P. Knepper,3 Peter Eichhorn,4 and Alasdair M. Cook1*

Department of Biology, The University of Konstanz, D-78457 Konstanz, Germany,1 School of Biotechnology and Biomolecular Sciences and Centre for Marine Biofouling and BioInnovation, University of New South Wales, Sydney, NSW 2052, Australia,2 Europa Institute of Applied Sciences Fresenius, D-65510 Idstein, Germany,3 State University of New York at Buffalo, Buffalo, New York 142604

Received 20 March 2007/ Accepted 1 June 2007

Commercial linear alkylbenzenesulfonate (LAS) contains 20 congeners of linear alkanes (C10 to C13) substituted subterminally with the 4-sulfophenyl moiety in any position from lateral to central. Parvibaculum lavamentivorans DS-1T degrades each of eight laterally substituted congeners [e.g., 2-(4-sulfophenyl)decane (2-C10-LAS); herein, compounds are named systematically by chain length (e.g., C10) and by the position of the substituent on the chain (e.g., position 2)] to a major sulfophenyl carboxylate [SPC; here 3-(4-sulfophenyl)butyrate (3-C4-SPC)] and two minor products, namely, the {alpha},ß-unsaturated SPC (SPC-2H, here 3-C4-SPC-2H) and the SPC+2C (here 5-C6-SPC) species (D. Schleheck, T. P. Knepper, K. Fischer, and A. M. Cook, Appl. Environ. Microbiol. 70:4053-4063). The degradation of centrally substituted congeners by strain DS-1 was examined in this work. 5-C10-LAS yielded not only the predicted 4-C8-SPC, 4-C8-SPC-2H, and 6-C10-SPC (about 70% of products) but also sulfophenyl dicarboxylates (SPdC), i.e., C6-, C8-, and C10-SPdC. These were identified by electrospray ionization-mass spectrometry (ESI-MS) after separation by high-pressure liquid chromatography (HPLC). ESI ion-trap MS and ESI-time of flight-MS were used to confirm the identities of key intermediates. Different mixtures of congeners obtained by separation of commercial LAS by HPLC were degraded, and the degradative products were compared. If a congener carried the sulfophenyl substituent on the 5, 6, or 7 position, SPdCs were formed as well as SPC, SPC-2H, and SPC+2C, whereas the substituent on the 2, 3, or 4 position yielded only SPC, SPC-2H, and SPC+2C. Some 50 products were generated from the 20 LAS congeners: 11 major SPCs, each with an SPC-2H and an SPC+2C (i.e., 33 SPC and SPC-2H species), and about 17 SPdC species. A large array of compounds, many in low quantities, is thus generated by P. lavamentivorans DS-1 during the degradation of commercial LAS.

* Corresponding author. Mailing address: Department of Biology, The University of Konstanz, Universitätsstr. 10, D-78457 Konstanz, Germany. Phone: (49) 7531 88 4247. Fax: (49) 7531 88 2966. E-mail: alasdair.cook{at}uni-konstanz.de

{triangledown} Published ahead of print on 8 June 2007.

{dagger} Supplemental material for this article may be found at http://aem.asm.org/.

Applied and Environmental Microbiology, August 2007, p. 4725-4732, Vol. 73, No. 15
0099-2240/07/$08.00+0     doi:10.1128/AEM.00632-07
Copyright © 2007, American Society for Microbiology. All Rights Reserved.



This article has been cited by other articles:

  • Li, W., Ju, J., Rajski, S. R., Osada, H., Shen, B. (2008). Characterization of the Tautomycin Biosynthetic Gene Cluster from Streptomyces spiroverticillatus Unveiling New Insights into Dialkylmaleic Anhydride and Polyketide Biosynthesis. J. Biol. Chem. 283: 28607-28617 [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»