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Volumn 76, Issue 1, 2010, Pages 196-202

The missing link in linear alkylbenzenesulfonate surfactant degradation: 4-sulfoacetophenone as a transient intermediate in the degradation of 3-(4-sulfophenyl)butyrate by comamonas testosteroni KF-1

Author keywords

[No Author keywords available]

Indexed keywords

ACETYL-COA; ALKYLBENZENESULFONATE; BACTERIAL COMMUNITY; BAEYER-VILLIGER; COENZYME A; COMAMONAS TESTOSTERONI; CRUDE EXTRACT; CULTURE MEDIUM; DEGRADATION PATHWAYS; DEGRADATIVE PATHWAYS; ENZYME REACTION; MONOOXYGENATION; OXYGENASES; RING CLEAVAGE; SULFITE OXIDATION; SULFOPHENYL; SURFACTANT DEGRADATION; TRANSIENT FORMATION; TRANSIENT INTERMEDIATE;

EID: 76149107167     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.02181-09     Document Type: Article
Times cited : (13)

References (37)
  • 1
    • 0023506950 scopus 로고
    • Biodegradation of anionic surfactants
    • Cain, R. B. 1987. Biodegradation of anionic surfactants. Biochem. Soc. Trans. 15:7-22.
    • (1987) Biochem. Soc. Trans. , vol.15 , pp. 7-22
    • Cain, R.B.1
  • 2
    • 0034932579 scopus 로고    scopus 로고
    • Cloning of the genes for a 4-sulphocatechoi-oxidizing protocatechuate 3,4-dioxygenase from Hydrogenophaga intermedia S1 and identification of the amino acid residues responsible for the ability to convert 4-sulphocatechol
    • Contzen, M., S. Bürger, and A. Stolz. 2001. Cloning of the genes for a 4-sulphocatechoi-oxidizing protocatechuate 3,4-dioxygenase from Hydrogenophaga intermedia S1 and identification of the amino acid residues responsible for the ability to convert 4-sulphocatechol. Mol. Microbiol. 41:199-205.
    • (2001) Mol. Microbiol. , Issue.41 , pp. 199-205
    • Contzen, M.1    Bürger, S.2    Stolz, A.3
  • 3
    • 0000082006 scopus 로고
    • Hydroquinone as the ring-fission substrate in the catabolism of 4-ethylphenol and 4-hydroxyacetophenone by Pseudomonas pulida JD1
    • Darby, J. M., D. G. Taylor, and D. J. Hopper. 1987. Hydroquinone as the ring-fission substrate in the catabolism of 4-ethylphenol and 4-hydroxyacetophenone by Pseudomonas pulida JD1. J. Gen. Microbiol. 133:2137-2146.
    • (1987) J. Gen. Microbiol. , vol.133 , pp. 2137-2146
    • Darby, J.M.1    Taylor, D.G.2    Hopper, D.J.3
  • 4
    • 38849129995 scopus 로고    scopus 로고
    • Bacterial sulfite dehydrogenases in organotrophic metabolism: Separation and identification in Cupriavidus necator H16 and in Delftia acidovorans SPH-1
    • DOI 10.1099/mic.0.2007/011650-0
    • 4. Denger, K., S. Weinitschke, T. H. Smils, D. Schleheck, and A. M. Cook. 2008. Bacterial sulfite dehydrogenases in organotrophic metabolism: separation and identification in Cupriavidus necator H16 and in Delftia acidovorans SPH-1. Microbiology 154:256-263. (Pubitemid 351201405)
    • (2008) Microbiology , vol.154 , Issue.1 , pp. 256-263
    • Denger, K.1    Weinitschke, S.2    Smits, T.H.M.3    Schleheck, D.4    Cook, A.M.5
  • 5
    • 0002389080 scopus 로고
    • Some microbial enzymes involved in the biodégradation of sulphated surfactants
    • Dodgson, K. S., and F. F. White. 1983. Some microbial enzymes involved in the biodégradation of sulphated surfactants. Top. Enzyme Ferment. Biotechnol. 7:90-155.
    • (1983) Top. Enzyme Ferment. Biotechnol. , vol.7 , pp. 90-155
    • Dodgson, K.S.1    White, F.F.2
  • 6
    • 1542329592 scopus 로고    scopus 로고
    • Parvibaculum lavamentivorans converts linear alkylbenzenesulfonate (LAS) surfactant to sulfophenylcarboxylates, α,β-unsaturated sulfophenylcarboxyiates and sulfophenyldicarboxylates, which are degraded in communities
    • Dong, W., P. Eichhorn, S. Radajewski, D. Schleheck, K. Denger, T. P. Knepper, J. C. Murrell, and A. M. Cook. 2004. Parvibaculum lavamentivorans converts linear alkylbenzenesulfonate (LAS) surfactant to sulfophenylcarboxylates, α,β-unsaturated sulfophenylcarboxyiates and sulfophenyldicarboxylates, which are degraded in communities. J. Appl. Microbiol. 96:630-640.
    • (2004) J. Appl. Microbiol. , vol.96 , pp. 630-640
    • Dong, W.1    Eichhorn, P.2    Radajewski, S.3    Schleheck, D.4    Denger, K.5    Knepper, T.P.6    Murrell, J.C.7    Cook, A.M.8
  • 7
    • 0036139397 scopus 로고    scopus 로고
    • α,β-Unsaturated sulfophenylcarboxylate intermediates detected during aerobic degradation of linear alkylbenzenesulfonate (LAS) surfactant: Direct evidence for ω-oxygenation followed by β-oxidations by liquid chromatography-electrospray mass spectrometry
    • Eichhorn, P., and T. P. Knepper. 2002. α,β-Unsaturated sulfophenylcarboxylate intermediates detected during aerobic degradation of linear alkylbenzenesulfonate (LAS) surfactant: direct evidence for ω-oxygenation followed by β-oxidations by liquid chromatography- electrospray mass spectrometry. Environ. Toxicol. Chem. 21:1-8.
    • (2002) Environ. Toxicol. Chem. , vol.21 , pp. 1-8
    • Eichhorn, P.1    Knepper, T.P.2
  • 9
    • 0037134521 scopus 로고    scopus 로고
    • Identification of coenzyme M biosynthetic phosphosulfolactate synthase: A new family of sulfonate biosynthesizing enzymes
    • Graham, D. E., H. Xu, and R. H. White. 2002. Identification of coenzyme M biosynthetic phosphosulfolactate synthase: a new family of sulfonate biosynthesizing enzymes. J. Biol. Chem. 277:13421-13429.
    • (2002) J. Biol. Chem. , vol.277 , pp. 13421-13429
    • Graham, D.E.1    Xu, H.2    White, R.H.3
  • 10
    • 33750960096 scopus 로고    scopus 로고
    • Characterization of the genes encoding the 3-carboxy-cis,cis-muconate- lactonizing enzymes from the 4-sulfocatechol degradative pathways of Hydrogenophaga intermedia S1 and Agrobacterium radiobacter S2
    • DOI 10.1099/mic.0.29136-0
    • 10. Halak, S., T. Basta, S. Burger, M. Contzen, and A. Stolz. 2006. Characterization of the genes encoding the 3-carboxy-cis, cis-muconate- lactonizing enzymes from the 4-sulfocatechol degradative pathways of Hydrogenophaga intermedia Sl and Agrobacterium radiobacter S2. Microbiology 152:3207-3216. (Pubitemid 44734325)
    • (2006) Microbiology , vol.152 , Issue.11 , pp. 3207-3216
    • Halak, S.1    Basta, T.2    Burger, S.3    Contzen, M.4    Stolz, A.5
  • 11
    • 34948838374 scopus 로고    scopus 로고
    • 4-Sulfomuconolactone hydrolases from Hydrogenophaga intermedia Sl and Agrobacterium radiobacter S2
    • Halak, S., T. Basta, S. Burger, M. Contzen, V. Wray, D. H. Pieper, and A. Stolz. 2007. 4-Sulfomuconolactone hydrolases from Hydrogenophaga intermedia Sl and Agrobacterium radiobacter S2. J. Bacteriol. 189:6998-7006.
    • (2007) J. Bacteriol. , Issue.189 , pp. 6998-7006
    • Halak, S.1    Basta, T.2    Burger, S.3    Contzen, M.4    Wray, V.5    Pieper, D.H.6    Stolz, A.7
  • 12
    • 0033778868 scopus 로고    scopus 로고
    • Possible interactions within a methanotrophic-heterotrophic groundwater community able to transform linear alkylbenzenesulfonates
    • Hrsák, D., and A. Begonja. 2000. Possible interactions within a methanotrophic-heterotrophic groundwater community able to transform linear alkylbenzenesulfonates. Appl. Environ. Microbiol. 66:4433-4439.
    • (2000) Appl. Environ. Microbiol. , vol.66 , pp. 4433-4439
    • Hrsák, D.1    Begonja, A.2
  • 13
    • 0034857466 scopus 로고    scopus 로고
    • 4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB. A novel flavoprotein catalyzing Baeyer-Villiger oxidation of aromatic compounds
    • Kamerbeek, N. M., M. J. Moonen, J. G. Van Der Ven, W. J. Van Berkel, M. W. Fraaije, and D. B. Janssen. 2001. 4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB. A novel flavoprotein catalyzing Baeyer-Villiger oxidation of aromatic compounds. Eur. J. Biochem. 268: 2547-2557.
    • (2001) Eur. J. Biochem. , vol.268 , pp. 2547-2557
    • Kamerbeek, N.M.1    Moonen, M.J.2    Van Der Ven, J.G.3    Van Berkel, W.J.4    Fraaije, M.W.5    Janssen, D.B.6
  • 14
    • 0014270238 scopus 로고
    • Enzymes of the mandelate pathway in bacterium N.C.I.B. 8250
    • Kennedy, S. I. T., and C. A. Fewson. 1968. Enzymes of the mandelate pathway in bacterium N.C.I.B. 8250. Biochem. J. 107:497-506.
    • (1968) Biochem. J. , Issue.107 , pp. 497-506
    • Kennedy, S.I.T.1    Fewson, C.A.2
  • 15
    • 14844295164 scopus 로고    scopus 로고
    • Surfactants: Properties, production, and environmental aspects
    • T. P. Knepper, D. Barceló, and P. de Voogt (ed.), Elsevier, Amsterdam, The Netherlands
    • Knepper, T. P., and J. L. Berna. 2003. Surfactants: properties, production, and environmental aspects, p. 1-50. In T. P. Knepper, D. Barceló, and P. de Voogt (ed.), Analysis and fate of surfactants in the aquatic environment. Elsevier, Amsterdam, The Netherlands.
    • (2003) Analysis and Fate of Surfactants in the Aquatic Environment , pp. 1-50
    • Knepper, T.P.1    Berna, J.L.2
  • 16
    • 0029278181 scopus 로고
    • Non-degraded metabolites arising from the biodegradation of commercial linear alkylbenzenesulfonate (LAS) surfactants in a laboratory trickling filter
    • Kölbener, P., U. Baumann, T. Leisinger, and A. M. Cook. 1995. Non-degraded metabolites arising from the biodegradation of commercial linear alkylbenzenesulfonate (LAS) surfactants in a laboratory trickling filter. Environ. Toxicol. Chem. 14:561-569.
    • (1995) Environ. Toxicol. Chem. , vol.14 , pp. 561-569
    • Kölbener, P.1    Baumann, U.2    Leisinger, T.3    Cook, A.M.4
  • 17
    • 0030980121 scopus 로고    scopus 로고
    • Taurine reduction in anaerobic respiration of Bilophila wadsworthia RZATAU
    • Laue, H., K. Denger, and A. M. Cook. 1997. Taurine reduction in anaerobic respiration of Bilophila wadsworthia RZATAU. Appl. Environ. Microbiol. 63:2016-2021.
    • (1997) Appl. Environ. Microbiol. , vol.63 , pp. 2016-2021
    • Laue, H.1    Denger, K.2    Cook, A.M.3
  • 18
    • 0029974571 scopus 로고    scopus 로고
    • Bacterial desulfonation of the ethanesulfonate metabolite of the chloroacetanilide herbicide metazachlor
    • Laue, H., J. A. Field, and A. M. Cook. 1996. Bacterial desulfonation of the ethanesulfonate metabolite of the chloroacetanilide herbicide metazachlor. Environ. Sci. Technol. 30:1129-1132.
    • (1996) Environ. Sci. Technol. , vol.30 , pp. 1129-1132
    • Laue, H.1    Field, J.A.2    Cook, A.M.3
  • 19
    • 1342329425 scopus 로고    scopus 로고
    • Differentiation and quantification of linear alkyl benzenesulfonate isomers by liquid chromatography-ion-trap mass spectrometry
    • DOI 10.1016/j.chroma.2003.08.071
    • 19. Lunar, L., S. Rubio, and D. Perez-Bendito. 2004. Differentiation and quantification of linear alkyl benzenesulfonate isomers by liquid chromatographyion-trap mass spectrometry. J. Chromatogr. A 1031:17-25. (Pubitemid 38264214)
    • (2004) Journal of Chromatography A , vol.1031 , Issue.1-2 , pp. 17-25
    • Lunar, L.1    Rubio, S.2    Perez-Bendito, D.3
  • 22
    • 2442419885 scopus 로고    scopus 로고
    • Chiralily of pollutants - Effects on metabolism and fate
    • Müller, T. A., and H.-P. E. Kohler. 2004. Chiralily of pollutants - effects on metabolism and fate. Appl. Microbiol. Biotechnol. 64:300-316.
    • (2004) Appl. Microbiol. Biotechnol. , vol.64 , pp. 300-316
    • Müller, T.A.1    Kohler, H.-P.E.2
  • 23
    • 0032786892 scopus 로고    scopus 로고
    • Acetone formation in the Vibrio family: A new pathway for bacterial leucine catabolism
    • Nemecek-Marshall, M., C. Wojciechowski, W. P. Wagner, and R. Fall. 1999. Acetone formation in the Vibrio family: a new pathway for bacterial leucine catabolism. J. Bacteriol. 181:7493-7499.
    • (1999) J. Bacteriol. , vol.181 , pp. 7493-7499
    • Nemecek-Marshall, M.1    Wojciechowski, C.2    Wagner, W.P.3    Fall, R.4
  • 24
    • 66249142686 scopus 로고    scopus 로고
    • Cloning, expression, characterization, and biocatalytic investigation of the 4-hydroxyacetophenone monooxygenase from Pseudomonas pulida JD1
    • Rehdorf, J., C. L. Zimmer, and U. T. Bornscheuer. 2009. Cloning, expression, characterization, and biocatalytic investigation of the 4-hydroxyacetophenone monooxygenase from Pseudomonas pulida JD1. Appl. Environ. Microbiol. 75:3106-3114.
    • (2009) Appl. Environ. Microbiol. , vol.75 , pp. 3106-3114
    • Rehdorf, J.1    Zimmer, C.L.2    Bornscheuer, U.T.3
  • 25
    • 0347600146 scopus 로고
    • Anionic synthetic detergents and water supply problems
    • Sawyer, C. N., and D. W. Ryckman. 1957. Anionic synthetic detergents and water supply problems. J. Am. "Water "Works Assoc. 49:480-490.
    • (1957) J. Am. "Water "Works Assoc. , vol.49 , pp. 480-490
    • Sawyer, C.N.1    Ryckman, D.W.2
  • 26
    • 0037334268 scopus 로고    scopus 로고
    • Saccharin as a sole source of carbon and energy for Sphingomonas xenophaga SKN
    • Schleheck, D., and A. M. Cook. 2003. Saccharin as a sole source of carbon and energy for Sphingomonas xenophaga SKN. Arch. Microbiol. 179:191-196.
    • (2003) Arch. Microbiol. , vol.179 , pp. 191-196
    • Schleheck, D.1    Cook, A.M.2
  • 27
    • 34547797333 scopus 로고    scopus 로고
    • T degrades centrally-substituted congeners of commercial linear alkylbenzenesulfonate (LAS) to sultbphenyl carboxylates and sulfophenyl dicarboxylates
    • T degrades centrally-substituted congeners of commercial linear alkylbenzenesulfonate (LAS) to sultbphenyl carboxylates and sulfophenyl dicarboxylates. Appl. Environ. Microbiol. 73:4725-4732.
    • (2007) Appl. Environ. Microbiol. , vol.73 , pp. 4725-4732
    • Schleheck, D.1    Knepper, T.2    Eichhorn, P.3    Cook, A.M.4
  • 28
    • 3242753673 scopus 로고    scopus 로고
    • Mineralization of individual congeners of linear alkylbenzenesulfonate (LAS) by defined pairs of heterotrophic bacteria
    • Schlebeck, D., T. P. Knepper, K. Fischer, and A. M. Cook. 2004. Mineralization of individual congeners of linear alkylbenzenesulfonate (LAS) by defined pairs of heterotrophic bacteria. Appl. Environ. Microbiol. 70:4053-4063.
    • (2004) Appl. Environ. Microbiol. , vol.70 , pp. 4053-4063
    • Schlebeck, D.1    Knepper, T.P.2    Fischer, K.3    Cook, A.M.4
  • 29
    • 5444261797 scopus 로고    scopus 로고
    • Parvibaculum lavamentivorans gen. nov., spec, nov., a novel heterotroph that initiates catabolism of linear alkylbenzenesulfonate
    • Schleheck, D., B. Tindall, R. Rossello-Mora, and A. M. Cook. 2004. Parvibaculum lavamentivorans gen. nov., spec, nov., a novel heterotroph that initiates catabolism of linear alkylbenzenesulfonate. Int. J. Syst. Evol. Microbiol. 54:1489-1497.
    • (2004) Int. J. Syst. Evol. Microbiol. , vol.54 , pp. 1489-1497
    • Schleheck, D.1    Tindall, B.2    Rossello-Mora, R.3    Cook, A.M.4
  • 30
    • 0034095435 scopus 로고    scopus 로고
    • Enantiomeric degradation of 2-(4-sulfophenyl)butyrate via 4-sulfocatechol in Delftia acidovorans SPB1
    • Schulz, S., W. Dong, U. Groth, and A. M. Cook. 2000. Enantiomeric degradation of 2-(4-sulfophenyl)butyrate via 4-sulfocatechol in Delftia acidovorans SPB1. Appl. Environ. Microbiol. 66:1905-1910.
    • (2000) Appl. Environ. Microbiol. , vol.66 , pp. 1905-1910
    • Schulz, S.1    Dong, W.2    Groth, U.3    Cook, A.M.4
  • 31
    • 0029911753 scopus 로고    scopus 로고
    • Enantioselective metabolism of chiral 3-phenylbutyric acid, an intermediate of linear alkylbenzene degradation, by Rhodococcus rhodochrous PB1
    • 31. Simoni, S., S. Klinke, C. Zipper, W. Angst, and H.-P. E. Kohler. 1996. Enantioselective metabolism of chiral 3-phenylbutyric acid, an intermediate of linear alkylbenzene degradation, by Rhodococcus rhodochrous PB1. Appl. Environ. Microbiol. 62:749-755. (Pubitemid 26074175)
    • (1996) Applied and Environmental Microbiology , vol.62 , Issue.3 , pp. 749-755
    • Simoni, S.1    Klinke, S.2    Zipper, C.3    Angst, W.4    Kohler, H.-P.E.5
  • 32
    • 0023082772 scopus 로고
    • Sulfate: Turbidimetric and nephelometric methods
    • Sörbo, B. 1987. Sulfate: turbidimetric and nephelometric methods. Methods Enzymol. 143:3-6.
    • (1987) Methods Enzymol. , vol.143 , pp. 3-6
    • Sörbo, B.1
  • 34
    • 0034459726 scopus 로고    scopus 로고
    • Conversion of 4-hydroxyacetophenone into 4-phenyl acetate by a flavin adenine dinucleotide-containing Baeyer-Villiger-type monooxygenase
    • DOI 10.1128/JB.182.23.6565-6569.2000
    • 34. Tanner, A., and D. J. Hopper. 2000. Conversion of 4-hydroxyacetophenone into 4-phenyl acetate by a flavin adenine dinudeotide-containing Baeyer-Villiger-type monooxygenase. J. Bacteriol. 182:6565-6569. (Pubitemid 32249234)
    • (2000) Journal of Bacteriology , vol.182 , Issue.23 , pp. 6565-6569
    • Tanner, A.1    Hopper, D.J.2
  • 35
    • 0022621550 scopus 로고
    • Orthanilic acid and analogues as carbon sources for bacteria: Growth physiology and enzymic desulphonation
    • Thurnheer, T., T. Köhler, A. M. Cook, and T. Lelsinger. 1986. Orthanilic acid and analogues as carbon sources for bacteria: growth physiology and enzymic desulphonation. J. Gen. Microbiol. 132:1215-1220.
    • (1986) J. Gen. Microbiol. , vol.132 , pp. 1215-1220
    • Thurnheer, T.1    Köhler, T.2    Cook, A.M.3    Lelsinger, T.4
  • 36
    • 0030111634 scopus 로고    scopus 로고
    • Complete degradation of xenobiotic surfactants by consortia of aerobic organisms
    • van Ginkel, C. G. 1996. Complete degradation of xenobiotic surfactants by consortia of aerobic organisms. Biodegradation 7:151-164.
    • (1996) Biodegradation , vol.7 , pp. 151-164
    • Van Ginkel, C.G.1
  • 37
    • 0002228325 scopus 로고
    • Biodegradation of anionic surfactants and related molecules
    • C. Ratledge (ed.), Kluwer Academic Publishers, Dordrecht, the Netherlands
    • White, G. F., and N. J. Russell. 1994. Biodegradation of anionic surfactants and related molecules, p. 143-177. In C. Ratledge (ed.), Biochemistry of microbial degradation. Kluwer Academic Publishers, Dordrecht, the Netherlands.
    • (1994) Biochemistry of Microbial Degradation , pp. 143-177
    • White, G.F.1    Russell, N.J.2


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