title: Parvibaculum lavamentivorans DS-1T degrades centrally substituted congeners of commercial linear alkylbenzenesulfonate to sulfophenyl carboxylates and sulfophenyl dicarboxylates.
abstract: Commercial linear alkylbenzenesulfonate (LAS) contains 20 congeners of linear alkanes (C(10) to C(13)) substituted subterminally with the 4-sulfophenyl moiety in any position from lateral to central. Parvibaculum lavamentivorans DS-1(T) 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., C(10)) 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,beta-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.
authors.affiliation: Department of Biology, The University of Konstanz, Universitätsstr 10, Konstanz, Germany.
authors.forename: David
authors.initials: D
authors.lastname: Schleheck
authors.forename: Thomas P
authors.initials: TP
authors.lastname: Knepper
authors.forename: Peter
authors.initials: P
authors.lastname: Eichhorn
authors.forename: Alasdair M
authors.initials: AM
authors.lastname: Cook
mesh_terms: D017738:Alkanesulfonic Acids / Q000378:metabolism*; D020561:Alphaproteobacteria / Q000254:growth & development / Q000378:metabolism*; D001431:Bacteriological Techniques; D001673:Biodegradation, Environmental; D001709:Biotechnology; D002264:Carboxylic Acids / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D021241:Spectrometry, Mass, Electrospray Ionization; D013501:Surface-Active Agents / Q000378:metabolism
chemical_list: D017738:Alkanesulfonic Acids; D002264:Carboxylic Acids; D013501:Surface-Active Agents; C030641:alkylbenzyl sulfonic acid