Anaerobic Desulfonation of 4-Tolylsulfonate and 2-(4-Sulfophenyl) Butyrate by a Clostridium sp

Denger, Karin; Kertesz, Michael A.; Vock, Esther; Schön, Roberto; Mägli, Andreas; Cook, Alasdair M.

doi:10.1128/aem.62.5.1526-1530.1996

Cited by 39 publications

(26 citation statements)

References 33 publications

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“…Under anaerobic conditions, sulfonates and sulfate esters can in principle provide not only a source of assimilable sulfur but can also be used in dissimilatory pathways (reviewed recently by Cook et al [7] and by Lie et al [8]). The ¢rst anaerobes reported to assimilate sulfonate sulfur were C. pasteurianum C1, which desulfurizes isethionate, taurine, or toluenesulfonate [314] and Clostridium beijerincki EV4, which grows with toluenesulfonate as sulfur source [315]. The mechanism by which this aromatic desulfonation takes place is still unclear, but is clearly di¡erent from the desulfonative process catalyzed by P. putida.…”

Section: Organosulfur Utilization Without Oxygenmentioning

confidence: 99%

Riding the sulfur cycle – metabolism of sulfonates and sulfate esters in Gram-negative bacteria

2000

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Sulfonates and sulfate esters are widespread in nature, and make up over 95% of the sulfur content of most aerobic soils. Many microorganisms can use sulfonates and sulfate esters as a source of sulfur for growth, even when they are unable to metabolize the carbon skeleton of the compounds. In these organisms, expression of sulfatases and sulfonatases is repressed in the presence of sulfate, in a process mediated by the LysR-type regulator protein CysB, and the corresponding genes therefore constitute an extension of the cys regulon. Additional regulator proteins required for sulfonate desulfonation have been identified in Escherichia coli (the Cbl protein) and Pseudomonas putida (the AsfR protein). Desulfonation of aromatic and aliphatic sulfonates as sulfur sources by aerobic bacteria is oxygendependent, carried out by the K-ketoglutarate-dependent taurine dioxygenase, or by one of several FMNH 2 -dependent monooxygenases. Desulfurization of condensed thiophenes is also FMNH 2 -dependent, both in the rhodococci and in two Gram-negative species. Bacterial utilization of aromatic sulfate esters is catalyzed by arylsulfatases, most of which are related to human lysosomal sulfatases and contain an active-site formylglycine group that is generated post-translationally. Sulfate-regulated alkylsulfatases, by contrast, are less well characterized. Our increasing knowledge of the sulfur-regulated metabolism of organosulfur compounds suggests applications in practical fields such as biodesulfurization, bioremediation, and optimization of crop sulfur nutrition. ß

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Section: Organosulfur Utilization Without Oxygenmentioning

confidence: 99%

Riding the sulfur cycle – metabolism of sulfonates and sulfate esters in Gram-negative bacteria

2000

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“…Even though a connection between bioavailability in anaerobic reactors and biodegradation has been established, very little data is available concerning anaerobic LAS biodegradation. A pure culture or a consortium of microorganisms capable of degrading LAS has so far never been reported, though the study of anaerobic degradation of sulfonated compounds is receiving increased attention [21][22][23][24].…”

Section: Uasb Reactor Experimentsmentioning

confidence: 99%

Anaerobic Degradation of Linear Alkylbenzene Sulfonate

Mogensen¹,

Haagensen²,

Ahring³

2003

Environ Toxicol Chem

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Linear alkylbenzene sulfonate (LAS) found in wastewater is removed in the wastewater treatment facilities by sorption and aerobic biodegradation. The anaerobic digestion of sewage sludge has not been shown to contribute to the removal. The concentration of LAS based on dry matter typically increases during anaerobic stabilization due to transformation of easily degradable organic matter. Hence, LAS is regarded as resistant to biodegradation under anaerobic conditions. We present data from a lab-scale semi-continuously stirred tank reactor (CSTR) spiked with linear dodecylbenzene sulfonate (C12 LAS), which show that C12 LAS was biodegradable under methanogenic conditions. Sorption of C12 LAS on sewage sludge was described with a Freundlich isotherm. The C12 LAS sorption was determined with different concentrations of total solids (TS). In the semi-continuously stirred tank reactor, 18% of the added C12 LAS was bioavailable and 20% was biotransformed when spiking with 100 mg/L of C12 LAS and a TS concentration of 14.2 mg/L. Enhanced bioavailability of C12 LAS was obtained in an upflow anaerobic sludge blanket (UASB) reactor inoculated with granular sludge and sewage sludge. Biodegradation under thermophilic conditions was 37% with LAS as sole carbon source. Benzaldehyde was produced in the UASB reactor during LAS transformation.

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“…Assimilation of the sulfonate sulfur of taurine (5) can be catalyzed by many anaerobes, e.g. C. pasteurianum and C. beijerinckii EV4 [156,158], and as this reaction also involves a taurine transaminase in C. pasteurianum [157] a sulfoacetaldehyde sulfo-lyase (III) is surely also involved ; the R-SH represents, e.g. a sulfur amino acid.…”

Section: Aerobes Assimilating Sulfonate-sulfurmentioning

confidence: 99%

“…Denger et al initially identi¢ed only strains of Clostridium in their work on arenesulfonates and alkanesulfonates [158,159], but the anaerobic desulfonation is also found in an unidenti¢ed, facultatively anaerobic bacterium [160]. Growth is concomitant with substrate utilization and molar growth yields are independent of the sulfur growth substrate.…”

Section: Anaerobes Assimilating Sulfonate-sulfurmentioning

confidence: 99%

“…Besides the naturally occurring, activated sulfonates taurine, cysteate and isethionate [156], the non-activated compounds ethanesulfonate and 1-heptanesulfonate [159] and arenesulfonates [158^160] are used as sole source of sulfur; all organisms catalyze the same arenesulfonatase reaction [160]. In contrast to Clostridium beijerinckii EV4, able to desulfonate only the activated alkanesulfonate taurine and arenesulfonates [158], three Clostridium spp. are able to utilize in addition the non-activated alkanesulfonates [159] (Table 2).…”

Section: Anaerobes Assimilating Sulfonate-sulfurmentioning

confidence: 99%

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Microbial desulfonation

Cook

1998

FEMS Microbiology Reviews

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Organosulfonates are widespread compounds, be they natural products of low or high molecular weight, or xenobiotics. Many commonly found compounds are subject to desulfonation, even if it is not certain whether all the corresponding enzymes are widely expressed in nature. Sulfonates require transport systems to cross the cell membrane, but few physiological data and no biochemical data on this topic are available, though the sequences of some of the appropriate genes are known. Desulfonative enzymes in aerobic bacteria are generally regulated by induction, if the sulfonate is serving as a carbon and energy source, or by a global network for sulfur scavenging (sulfate starvation induced (SSI) stimulon) if the sulfonate is serving as a source of sulfur. It is unclear whether an SSI regulation is found in anaerobes. The anaerobic bacteria examined can express the degradative enzymes constitutively, if the sulfonate is being utilized as a carbon source, but enzyme induction has also been observed. At least three general mechanisms of desulfonation are recognisable or postulated in the aerobic catabolism of sulfonates: (1) activate the carbon neighboring the C y Q bond and release of sulfite assisted by a thiamine pyrophosphate cofactor; (2) destabilize the C y Q bond by addition of an oxygen atom to the same carbon, usually directly by oxygenation, and loss of the good leaving group, sulfite; (3) an unidentified, formally reductive reaction. Under SSIS control, different variants of mechanism (2) can be seen. Catabolism of sulfonates by anaerobes was discovered recently, and the degradation of taurine involves mechanism (1). When anaerobes assimilate sulfonate sulfur, there is one common, unknown mechanism to desulfonate the inert aromatic compounds and another to desulfonate inert aliphatic compounds; taurine seems to be desulfonated by mechanism (1).

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Anaerobic Desulfonation of 4-Tolylsulfonate and 2-(4-Sulfophenyl) Butyrate by a Clostridium sp

Cited by 39 publications

References 33 publications

Riding the sulfur cycle – metabolism of sulfonates and sulfate esters in Gram-negative bacteria

Riding the sulfur cycle – metabolism of sulfonates and sulfate esters in Gram-negative bacteria

Anaerobic Degradation of Linear Alkylbenzene Sulfonate

Microbial desulfonation

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