Desulfonation of Biotransformation Products From Commercial Linear Alkylbenzenesulfonates

Dong

Denger

et al. 2000

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The surfactant linear alkylbenzenesulfonate (LAS; 0.5 mM) or linear monoalkyldiphenyletherdisulfonate (LADPEDS; 0.5 mM) in salts medium was easily degraded in laboratory trickling filters, whereas carbonlimited, aerobic enrichment cultures in suspended culture with the same inocula did not grow. We took portions of the trickling filters which degraded LADPEDS, shook the organisms from the solid support (polyester), and found that growth in suspended culture in LADPEDS-salts medium occurred only in the presence of some solid support (polyester fleece or glass wool), though little biomass was immobilized on the support. The end products in suspended culture were identical with those from the trickling filters. There was low plating efficiency of LADPEDS-grown cultures on complex medium, and no picked colony or mixture of colonies grew in LADPEDS-salts-glass wool medium. However, selective plates containing LADPEDS-salts medium solidified with agarose yielded LADPEDS-dependent, pinpoint colonies which could be picked singly and subcultured in selective liquid medium. Isolate DS-1 was a bacterium which showed 93% sequence homology (16S ribosomal DNA) to its nearest phylogenetic neighbor, an ␣-proteobacterium. Strain DS-1 grew heterotrophically in LADPEDS-salts-glass wool medium and converted the set of aryl-substituted alkanes to the corresponding aryl-substituted carboxylic acids of shorter chain length. Similarly, strain DS-1 grew heterotrophically with commercial LAS, converting it to a set of sulfophenylcarboxylates. Growth with a single isomer of LAS [3-(4-sulfophenyl)dodecane] was concomitant with excretion of 4-(4-sulfophenyl)hexanoate, which was identified by matrix-assisted laser desorption ionization mass spectrometry. The growth yield (6.4 g of protein/mol of C) indicated mass balance, which, with the specific growth rate (0.05 h ؊1 ), indicated a specific utilization rate of LAS of 2.2 mkat/kg of protein.

mentioning

confidence: 99%

An α-Proteobacterium Converts Linear Alkylbenzenesulfonate Surfactants into Sulfophenylcarboxylates and Linear Alkyldiphenyletherdisulfonate Surfactants into Sulfodiphenylethercarboxylates

Dong

Denger

et al. 2000

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“…There were significant amounts of LADPEDS with chain lengths of C 10 , C 11 , and C 12 and traces with chain lengths of C 13 , C 14 , C 18 , and C 20 . The second major signal was near 34 min, where m/z was 473 (M-H) Ϫ , and this was presumed to be the monosulfonated diphenylether referred to in the manufacturer's description (see the legend to Fig.…”

Section: Resultsmentioning

confidence: 99%

“…This is especially useful with organosulfonates, because the general desulfonation of aromatic compounds yields the corresponding phenol (8), and the hydroxy analogue of a benzenesulfonate (i.e., the phenol) is generally degradable (35). Recent work indicates that a desulfonation of "recalcitrant" xenobiotic compounds could lead to their further degradation or binding to soil components (15,16,18,24,26).…”

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confidence: 99%

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Desulfonation and Degradation of the Disulfodiphenylethercarboxylates from Linear Alkyldiphenyletherdisulfonate Surfactants

Lechner

Schönenberger

et al. 2003

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Earlier work showed that the biodegradation of a commercial linear monoalkyldiphenyletherdisulfonate surfactant as a carbon source for microbial growth leads to the quantitative formation of corresponding disulfodiphenylether carboxylates (DSDPECs), which were not degraded. ␣-Proteobacterium strain DS-1 (DSM 13023) catalyzes these reactions. These DSDPECs have now been characterized by high-pressure liquid chromatography coupled via an electrospray interface to a mass spectrometer. DSDPECs were a complex mixture of compounds which indicated catabolism via -oxygenation and ␤-oxidation. DSDPECs were subject to quantitative desulfonation in bacterial cultures in which they served as sole sulfur sources for bacterial growth. On average, one sulfonate group per DSDPEC species was removed, and the organism responsible for this desulfonation was isolated and identified as Rhodococcus opacus ISO-5. The products were largely monosulfodiphenylether carboxylate-phenols (MSDPEC-phenols). MSDPEC-phenols were subject to extensive dissimilation by bacteria from activated sludge.The linear monoalkyldiphenyletherdisulfonate surfactants (LADPEDS) (Fig. 1) have been in use for some 40 years in industrial processes (22), which include the production of synthetic latex and its use in carpet production, paints, and paper coatings (13), as well as in subsurface remediation (22,25,27). Despite this widespread use of LADPEDS and their classification in the United States as biodegradable (25), little has been published on their metabolism. It was shown recently, however, that their initial metabolism in pure culture is analogous to that of the linear alkylbenzenesulfonate (LAS) surfactants, namely, -oxygenation and oxidation of the side chain followed by ␤-oxidation, which results in the release of the correspondingly smaller disulfodiphenylether carboxylate (DSDPEC) (Fig.

“…In most cases, sets of isomers, each with a different dominant congener, were obtained. Each fraction was subjected to treatment in a Rotavap to remove the acetonitrile and then desalted and concentrated by solid-phase extraction (10,14).…”

Section: Methodsmentioning

confidence: 99%

Parvibaculum lavamentivorans DS-1 ^T Degrades Centrally Substituted Congeners of Commercial Linear Alkylbenzenesulfonate to Sulfophenyl Carboxylates and Sulfophenyl Dicarboxylates

Knepper

Eichhorn

et al. 2007

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, 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 ESItime of flight-MS were used to confirm the identities of key intermediates. Different mixtures of congenersobtained 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.