Abstract
Due to their persistence, haloaromatics are compounds of environmental concern. Aerobically, bacteria degrade these compounds by mono- or dioxygenation of the aromatic ring. The common intermediate of these reactions is (halo)catechol. Halocatechol is cleaved either intradiol (ortho-cleavage) or extradiol (meta-cleavage). In contrast to ortho-cleavage, meta-cleavage of halocatechols yields toxic metabolites. Dehalogenation may occur fortuitously during oxygenation. Specific dehalogenation of aromatic compounds is performed by hydroxylases, in which the halo-substituent is replaced by a hydroxyl group. During reductive dehalogenation, haloaromatic compounds may act as electron-acceptors. Herewith, the halosubstituent is replaced by a hydrogen atom.
Similar content being viewed by others
Abbreviations
- CBz:
-
chlorobenzene
- DCBz:
-
dichlorobenzene
- TrCBz:
-
trichlorobenzene
- TCBz:
-
tetrachlorobenzene
- PCBz:
-
pentachlorobenzene
- HCBz:
-
hexachlorobenzene
- CBA:
-
chlorobenzoic acid
- BBA:
-
bromobenzoic acid
- FBA:
-
fluorobenzoic acid
- IBA:
-
iodobenzoic acid
- CP:
-
chlorophenol
- CA:
-
chloroaniline
- PCBs:
-
polychlorinated biphenyls
- CB:
-
chlorobiphenyl
- 2,4-D:
-
2,4-dichlorophenoxyacetic acid
- 2,4,5-T:
-
2,4,5-trichlorophenoxyacetic acid
References
Adriaens, P, Kohler, H-PE, Kohler-Staub, D & Focht, DD (1989) Bacterial dehalogenation of chlorobenzoates and coculture biodegradation of 4,4′-dichlorobiphenyl. Appl. Environ. Microbiol. 55: 887–892
Adriaens, P & Focht, DD (1990) Continuous coculture degradation of selected polychlorinated biphenyl congeners by Acinetobacter spp. in an aerobic reactor system. Environ. Sci. Technol. 24: 1042–1049
Allard, A-S, Remberger, M & Neilson, AH (1985) Bacterial O-methylation of chloroguaiacols: Effect of substrate concentration, cell density, and growth conditions. Appl. Environ. Microbiol. 49: 279–288
Apajalatiti, JHA & Salkinoja-Salonen, MS (1987a) Dechlorination and para-hydroxylation of polychlorinated phenols by Rhodococcus chlorophenolicus. J. Bacteriol. 169: 675–681
Apajalatiti, JHA & Salkinoja-Salonen, MS (1987b) Complete dechlorination of tetrachlorohydroquinone by cell extracts of pentachlorophenol-induced Rhodococcus chlorophenolicus. J. Bacteriol. 169: 5125–5130
Bailey, RE, Gonsior, SJ & Rhinehart, WL (1983) Biodegradation of the monochlorobiphenyls and biphenyl in river water. Environ. Sci. Technol. 17: 617–624
Ballschmiter, K & Scholz, C (1981) Primärschritte der Umwandlung von Chlorbenzol-Derivaten durch Pseudomonas putida. Angew. Chem. 93: 1026–1027
Baxter, RM & Sutherland, DA (1984) Biochemical and photochemical processes in the degradation of chlorinated biphenyls. Environ. Sci. Technol. 18: 608–610
Bedard, DL, Unterman, R, Bopp, LH, Brennan, MJ, Haberl, ML & Johnson, C (1986) Rapid assay for screening and characterizing microorganisms for the ability to degrade polychlorinated biphenyls. Appl. Environ. Microbiol. 51: 761–768
Bedard, DL, Wagner, RE, Brennan, MJ, Haberl, ME & Brown Jr, JF (1987a) Extensive degradation of Arochlors and environmentally transformed polychlorinated biphenyls by Alcaligenes eutrophus H850. Appl. Environ. Microbiol. 53: 1094–1102
Bedard, DL, Haberl, ML, May, RJ & Brennan, MJ (1987b) Evidence for novel mechanisms of polychlorinated biphenyl metabolism in Alcaligenes eutrophus H850. Appl. Environ. Microbiol. 53: 1103–1112
Bollag, JM, Helling, CS & Alexander, M (1968a) 2,4-D Metabolism: Enzymatic hydroxylation of chlorinated phenols. J. Agric. Food Chem. 16: 826–828
Bollag, JM, Briggs, GG, Dawson, JE & Alexander, M (1968b) 2,4-D Metabolism: Enzymatic degradation of chlorocatechols. J. Agric. Food Chem. 16: 829–833
de Bont, JAM, Vorage, MJAW, Hartmans, S & van den Tweel, WJJ (1986) Microbial Degradation of 1,3-Dichlorobenzene. Appl. Environ. Microbiol. 52: 677–680
Bopp, LH (1986) Degradation of highly chlorinated PCBs by Pseudomonas strain LB400. J. Ind. Microbiol. 1: 23–29
Bosma, TNP, Van der Meer, JR, Schraa, G, Tros, ME & Zehnder, AJB (1988) Reductive dechlorination of all trichloro- and dichlorobenzene isomers. FEMS Microbiol. Ecol. 53: 223–229
Boyd, SA & Shelton, DR (1984) Anaerobic biodegradation of chlorophenols in fresh and acclimated sludge. Appl. Environ. Microbiol. 47: 272–277
Brown Jr, JF, Bedard, DL, Brennan, MJ, Carnahan, JC, Feng, H & Wagner, RE (1987a) Polychlorinated biphenyl dechlorination in aquatic sediments. Science 236: 709–712
Brown Jr, JF, Wagner, RE, Feng, H, Bedard, DL, Brennan, MJ, Carnahan, JC & May, RJ (1987b) Environmental dechlorination of PCBs. Environ. Toxicol. Chem. 6: 579–593
Brunner, W, Sutherland, FH & Focht, DD (1985) Enhanced biodegradation of polychlorinated biphenyls in soil by analog enrichment and bacterial inoculation. J. Environ. Qual. 14: 324–328
Cain, RB, Trantner, EK & Darrah, JA (1968) The utilization of some halogenated aromatic acids by Nocardia: oxidation and metabolism. Biochem. J. 106: 211–227
Carney, BF, Kröckel, L, Leary, JV & Focht, DD (1989a) Identification of Pseudomonas alcalignes chromosomal DNA in the plasmid DNA of the chlorobenzene-degrading recombinant Pseudomonas putida strain CB1–9. Appl. Environ. Microbiol. 55: 1037–1039
Carney, BF & Leary, JV (1989b) Novel alterations in plasmid DNA associated with aromatic hydrocarbon utilization by Pseudomonas putida R5–3. Appl. Environ. Microbiol. 55: 1523–1530
Chatterjee, DK, Hamada, S & Chakrabarty, AM (1981) Plasmid specifying total degradation of 3-chlorobenzoate by a modified ortho pathway. J. Bacteriol. 146: 639–646
Chu, JP & Kirsch, EJ (1972) Metabolism of pentachlorophenol by an axenic bacterial culture. Appl. Environ. Microbiol. 23: 1033–1035
Clarke, KF, Callely, AG, Livingstone, A & Fewson, CA (1975) Metabolism of monofluorobenzoates by Acinetobacter calcoaceticus N.C.I.B. 8250: formation of monofluorocatechols. Biochim. Biophys. Acta 404: 169–179
Corke, CT, Bunce, NJ, Beaumont, AL & Merrick, RL (1979) Diazonium cations as intermediates in the microbial transformation of chloroanilines to chlorinated biphenyls, azo compounds, and triazenes. J. Agric. Food Chem. 27: 644–646
DeWeerd, KA, Suflita, JM, Linkfield, T, Tiedje, JM & Pritchard, PH (1986) The relationship between reductive dehalogenation and other aryl substituent removal reactions catalyzed by anaerobes. FEMS Microbiol. Ecol. 38: 331–339
DeWeerd, KA, Mandelco, L, Tanner, RS, Woese, CR & Suflita, JM (1990) Desulfomonile tiedjei gen nov and sp nov, a novel anaerobic dehalogenating sulfate-reducing bacterium. Arch. Microbiol. 154: 23–30
Dolfing, J & Tiedje, JM (1986) Hydrogen cycling in a three-tiered food web growing on the methanogenic conversion of 3-chlorobenzoate. FEMS Microbiol. Ecol. 38: 293–298
(1987) Growth yield increase linked to reductive dechlorination in a defined 3-chlorobenzoate degrading methanogenic coculture. Arch. Microbiol. 149: 102–105
Dolfing, J (1990) Reductive dechlorination of 3-chlorobenzoate is coupled to ATP production and growth in an anaerobic bacterium, strain DCB-1. Arch. Microbiol. 153: 264–266
Engelhardt, G, Rast, HG & Wallnöfer, PR (1979) Cometabolism of phenol and substituted phenols by Nocardia spec. DSM 43251. FEMS Microbiol. Lett. 5: 377–383
Engesser, KH & Schulte, P (1989) Degradation of 2-bromo-2-chloro- and 2-fluorobenzoate by Pseudomonas putida CLB 250. FEMS Microbiol. Lett. 60: 143–148
Engesser, KH, Auling, G, Busse, J & Knackmuss, H-J (1990) 3-Fluorobenzoate enriched bacterial strain FLB 300 degrades benzoate and all three isomeric monofluorobenzoates. Arch. Microbiol. 153: 193–199
Evans, WC, Smith, BSW, Fernley, HN & Davies, JI (1971) Bacterial Metabolism of 2,4-Dichlorophenoxyacetate. Biochem. J. 122: 543–552
Fathepure, BZ, Tiedje, JM & Boyd, SA (1988) Reductive dechlorination of hexachlorobenzene to tri- and dichlorobenzenes in anaerobic sewage sludge. Appl. Environ. Microbiol. 54: 327–330
Fetzner, S, Müller, R & Lingens, F (1989) A novel metabolite in the microbial degradation of 2-chlorobenzoate. Biochem. Biophys. Res. Commun. 161: 700–705
Focht, DD & Shelton, D (1987) Growth kinetics of Pseudomonas alcaligenes C-0 relative to inoculation and 3-chlorobenzoate metabolism in soil. Appl. Environ. Microbiol. 53: 1846–1849
Fries, GF & Marrow, GS (1984) Metabolism of chlorobiphenyls in soil. Bull. Environ. Contam. Toxicol. 33: 6–12
Furukawa, K (1982) Microbial degradation of polychlorinated biphenyls (PCBs). In: Chakrabarty, AM (Ed) Biodegradation and Detoxification of Environmental Pollutants CRC Boca Raton FLA (pp 33–57)
Gibson, SA & Suflita, JM (1990) Anaerobic degradation of 2,4,5-trichlorophenoxyacetic acid in samples from methanogenic aquifer: Stimulation by short-chain organic acids and alcohols. Appl. Environ. Microbiol. 56: 1825–1832
Goldman, P, Milne, GWA & Pignataro, MT (1967) Fluorine containing metabolites formed from 2-fluorobenzioc acid by Pseudomonas species. Arch. Biochem. Biophys. 118: 178–184
Groenewegen, PEJ, Driessen, AJM, Konings, WN & de Bont, JAM (1990) Energy-dependent uptake in the Coryneform bacterium NTB-1. J. Bacteriol. 172: 419–423
Haigler, BE, Nishino, SF & Spain, JC (1988) Degradation of 1,2-dichlorobenzene by a Pseudomonas sp. Appl. Environ. Microbiol. 54: 294–301
Haigler, BE & Spain, JC (1989) Degradation of p-chlorotoluene by a mutant of Pseudomonas sp. strain JS6. Appl. Environ. Microbiol. 55: 372–379
Häggblom, MM, Nohynek, LJ & Salkinoja-Salonen, MS (1988) Degradation and O-methylation of chlorinated phenolic compounds by Rhodococcus and Mycobacterium strains. Appl. Environ. Microbiol. 54: 3043–3052
Häggblom, MM, Janke, D & Salkinoja-Salonen, MS (1989a) Hydroxylation and dechlorination of tetrachlorohydroquinone by Rhodococcus sp. strain CP-2 cell extracts. Appl. Environ. Microbiol. 55: 516–519
Häggblom, MM, Janke, D, Middeldorp, PJM & Salkinoja-Salonen, MS (1989b) O-methylation of chlorinated phenols in the genus Rhodococcus. Arch. Microbiol. 152: 6–9
Hankin, L & Sawhney, BL (1984) Microbial Degradation of Polychlorinated Biphenyls in Soil. Soil Sci. 137: 401–407
Harms, H, Wittich, R-M, Sinnwell, V, Meyer, H, Fortnagel, P & Francke, W (1990) Transformation of dibenzo-p-dioxin by Pseudomonas sp. strain HH69. Appl. Environ. Microbiol. 56: 1157–1159
Hartmann, J, Reineke, W & Knackmuss, H-J (1979) Metabolism of 3-chloro-, 4-chloro-, and 3,5-dichlorobenzoate by a Pseudomonad. Appl. Environ. Microbiol. 37: 421–428
Hartmann, J, Engelberts, K, Nordhaus, B, Schmidt, E & Reineke, W (1989) Degradation of 2-chlorobenzoate by in vivo constructed hybrid Pseudomonads. FEMS Microbiol. Lett. 61: 17–22
Haugland, RA, Schlemm, DJ, Lyons III, RP, Sferra, PR & Chakrabarty, AM (1990) Degradation of the chlorinated phenoxyacetate herbicides 2,4-dichlorophenoxyacetic acid and 2,4,5-trichlorophenoxyacetic acid by pure and mixed bacterial cultures. Appl. Environ. Microbiol. 56: 1357–1362
Higson, FK & Focht, DD (1990) Degradation of 2-Bromobenzoic Acid by a Strain of Pseudomonas aeruginosa. Appl. Environ. Microbiol. 56: 1615–1619
Hiramoto, M, Ohtake, H & Toda, K (1989) A kinetic study on total degradation of 4-chlorobiphenyl by a two-step culture of Arthrobacter and Pseudomonas strains. J. Fermentation Bioeng. 1: 68–70
Horowitz, A, Suflita, JM & Tiedje, JM (1983) Reductive dehalogenations of halobenzoates by anaerobic lake sediment microorganisms. Appl. Environ. Microbiol. 45: 1459–1461
Horvath, M, Ditzelmüller, G, Loidl, M & Streichsbier, F (1990) Isolation and characterization of a 2-(2,4-dichlorophenoxy) propionic acid-degrading soil bacterium. Appl. Microbiol. Biotechnol. 33: 213–216
Janke, D, Al-Mofarji, T, Straube, G, Schumann, P & Prauser, H (1988a) Critical steps in the degradation of chloroaromatics by Rhodococci. I. Initial enzyme reactions involved in catabolism of aniline, phenol and benzoate by Rhodococcus sp. An 117 and An 213. J. Basic Microbiol. 8: 509–518
Janke, D, Al-Mofarji, T & Schukat, B (1988b) Critical steps in degradation of chloroaromatics by Rhodococci. II. Whole-cell turnover of different monochloroaromatic non-growth substrates by Rhodococcus sp. An 117 and An 213 in the absence/presence of glucose. J. Basic Microbiol. 8: 519–528
Johston, HW, Briggs, GG & Alexander, M (1972) Metabolism of 3-chlorobenzoic acid by a Pseudomonad. Soil. Biol. Biochem. 4: 187–190
Karns, JS, Kilbane, JJ, Duttagupta, S & Chakrabarty, AM (1983a) Metabolism of halophenols by 2,4,5-trichlorophenoxyacetic acid-degrading Pseudomonas cepacia. Appl. Environ. Microbiol. 46: 1176–1181
Karns, JS, Duttagupta, S & Chakrabarty, AM (1983b) Regulation of 2,4,5-trichlorophenoxyacetic acid and chlorophenol metabolism in Pseudomonas cepacia AC 1100. Appl. Environ. Microbiol. 46: 1182–1186
Keil, H, Klages, U & Lingens, F (1981) Degradation of 4-chlorobenzoate by Pseudomonas sp. CBS3: induction of catabolic enzymes. FEMS Microbiol. Lett. 10: 213–215
Kimbara, K, Hashimoto, T, Fukuda, M, Koana, T, Takagi, M, Oishi, M & Yano, K (1988) Isolation and characterization of a mixed culture that degrades polychlorinated biphenyls. Agric. Biol. Chem. 52: 2885–2891
King, GM (1988) Dehalogenation in marine sediments containing natural sources of halophenols. Appl. Environ. Microbiol. 54: 3079–3085
Klecka, GM & Gibson, DT (1980) Metabolism of dibenzo-p-dioxin and chlorinated dibenzo-p-dioxins by a Beijerinckia species. Appl. Environ. Microbiol. 39: 288–296
Knackmuss, H-J & Hellwig, M (1978) Utilization and cooxidation of chlorinated phenols by Pseudomonas sp. B13. Arch. Microbiol. 117: 1–7
Kong, H-Y & Sayler, GS (1983) Degradation and total mineralization of monohalogenated biphenyls in natural sediment and mixed microbial culture. Appl. Environ. Microbiol. 46: 666–672
Konopka, A, Knight, D & Turco, RF (1989) Characterization of a Pseudomonas sp. capable of aniline degradation in the presence of secondary carbon sources. Appl. Environ. Microbiol. 55: 385–389
Kröckel, L & Focht, DD (1987) Construction of chlorobenzeneutilizing recombinants by progressive manifestation of a rare event. Appl. Environ. Microbiol. 53: 2470–2475
Kuhn, EP & Suflita, JM (1989) Sequential reductive dehalogenation of chloroanilines by microorganisms from a methanogenic aquifer. Environ. Sci. Technol. 23: 848–852
Lammerding, AM, Bunce, NJ, Merrick, RL & Corke, CT (1982) Structural effects on the microbial diazotization of anilines. J. Agric. Food Chem. 30: 644–647
Lehrbach, RP, Zeyer, J, Reineke, W, Knackmuss, H-J & Timmis, KN (1984) Enzyme Recruitment in vitro: Use of Clones Genes to Extend the Range of Haloaromatics Degraded by Pseudomonas sp. strain B13. J. Bacteriol. 158: 1025–1032
Linkfield, TG & Tiedje, JM (1990) Characterization of the requirements and substrates for reductive dehalogenation by strain DCB-1. J. Ind. Microbiol. 5: 9–16
Marinucci, AC & Bartha, R (1979) Biodegradation of 1,2,3- and 1,2,4-trichlorobenzene in soil and in liquid enrichment culture. Appl. Environ. Microbiol. 38: 811–817
Marks, TS, Smith, ARW & Quirk, AV (1984a) Degradation of 4-chlorobenzoic acid by Arthrobacter sp. Appl. Environ. Microbiol. 48: 1020–1025
Marks, TS, Wait, R, Smith, ARW & Quirk, AV (1984b) The origin of the oxygen incorporated during the dehalogenation/hydroxylation of 4-chlorobenzoic acid by an Arthrobacter sp. Biochem. Biophys. Res. Commun. 124: 669–674
van der Meer, JR, Roelofsen, W, Schraa, G & Zehnder, AJB (1987) Degradation of Low Concentrations of Dichlorobenzenes and 1,2,4-Trichlorobenzene by Pseudomonas sp. P51 in Nonsterile Soil Columns. FEMS Microbiol. Ecol. 45: 333–341
Mikesell, MD & Boyd, SA (1986) Complete reductive dechlorination and mineralization of pentachlorophenol by anaerobic microorganisms. Appl. Environ. Microbiol. 52: 861–865
Milne, GWA, Goldman, P & Holtzman, JL (1968) The metabolism of 2-fluorobenzoic acid: studies with 18O2. J. Biol. Chem. 243: 5374–5376
Minard, RD, Russel, S & Bollag, JM (1977) Chemical transformation of 4-chloroaniline to a triazene in a bacterial culture medium. J. Agric. Food Chem. 25: 841
Mohn, WW, Linkfield, TG, Pankratz, HS & Tiedje, JM (1990) Involvement of a collar structure in polar growth and cell division of strain DCB-1. Appl. Environ. Microbiol. 56: 1206–1211
Mohn, WM & Tieje, JM (1990) Strain DCB-1 conserves energy for growth from reductive dechlorination coupled to formate oxidation. Arch. Microbiol. 153: 267–271
Müller, R, Thiele, J, Klages, U & Lingens, F (1984) Incorporation of [18O H2O] water into 4-hydroxybenzoic acid in the reaction of 4-chlorobenzoate dehalogenase from Pseudomonas spec. CBS3. Biochem. Biophys. Res. Commun. 124: 178–182
Müller, R, Oltmans, RH & Lingens, F (1988) Enzymic dehalogenation of 4-chlorobenzoate by extracts from Arthrobacter sp. SU DSM 20407. Biol. Chem. Hoppe-Seyler 369: 567–571
Neilson, AH, Lindgren, C, Hynning, P-A & Remberger, M (1988) Methylation of halogenated phenols and thiophenols by cell extracts of Gram-positive and Gram-negative bacteria. Appl. Environ. Microbiol. 54: 524–530.
Ohmori, T, Ikai, T, Minoda, Y & Yamada, K (1973) Utilization of Hydrocarbons by Microorganisms. XXV. Utilization of Polyphenyl and Polyphenyl-related Compounds by Microorganimsms. Agric. Biol. Chem. 37: 1599–1605
Oltmanns, RH, Müller, R, Otto, MK & Lingens, F (1989) Evidence for a new pathway in the bacterial degradation of 4-fluorobenzoate. Appl. Environ. Microbiol. 55: 2499–2504
Pardue, JH, Delaune, RD & Patrick Jr., WH (1988) Effect of sediment pH and oxidation-reduction potential on PCB mineralization. Water Air Soil Pollut. 37: 439–447
Parsons, J, Veerkamp, W & Hutzinger, O (1983) Microbial metabolism of chlorobiphenyls. Toxicol. Environ. Chem. 6: 327–350
Parsons, JR, Sijm, DTHM, van Laar, A & Hutzinger, O (1988) Biodegradation of chlorinated biphenyls and benzoic acids by a Pseudomonas strain. Appl. Microbiol. Biotechnol. 29: 81–84
Parsons, JR & Storms, MCM (1989) Biodegradation of chlorinated dibenzo-p-dioxins in batch and continuous cultures of strain JB1. Chemosphere 19: 1297–1308
Parsons, JR, Ratsak, C & Siekerman, C (1990) Biodegradation of chlorinated dibenzofurans by an Alcaligenes strain. In: Hutzinger, O and Fiedler, H (Eds) Organohalogen Compounds. Proc. Dioxin '90-EPRI Seminar, Sept. 10–14, 1990, Bayreuth, Vol 1 (pp 377–380). Ecoinforma Press, Bayreuth, F.R.G.
Pettigrew, CA, Breen, A, Corcoran, C & Sayler, GS (1990) Chlorinated Biphenyl Mineralization by Individual Populations and Consortia of freshwater Bacteria. Appl. Environ. Microbiol. 56: 2036–2045
Philippi, M, Schmid, J, Wipf, HK & Hütter, RA (1982) A microbial metabolite of TCDD. Experientia 38: 659–661
Pieper DH, Reineke W, Engesser K-H, Knackmuss H-J (1988) Metabolism of 2,4-dichlorophenoxyacetic acid, 4-chloro-2-methylphenoxyacetic acid and 2-methylphenoxyacetic acid by Alcaligenes eutrophus JMP 134.
Quensen III, JF & Matsumura, F (1983) Oxidative degradation of 2,3,7,8-tetrachlorodibenzo-p-dioxin by microorganisms. Environ. Toxicol. Chem. 2: 261–268
Quensen III, JF, Tiedje, JM & Boyd, SA (1988) Reductive dechlorination of polychlorinated biphenyls by anaerobic microorganisms from sediments. Science 242: 752–754
Quensen III, JF, Boyd, SA & Tiedje, JM (1990) Dechlorination of Four Commercial Polychlorinated Biphenyl Mixtures (Aroclors) by Anaerobic Microorganisms from Sediments. Appl. Environ. Microbiol. 56: 2360–2369
Reineke, W (1984) Microbial degradation of halogenated aromatic compounds. Microbiol. Ser. 13: 319–360
Reineke, W & Knackmuss, H-J (1984) Microbial metabolism of haloaromatics. Isolation and properties of a chlorobenzenedegrading bacterium. Appl. Environ. Microbiol. 47: 395–402
Reineke, W & Knackmuss, H-J (1988) Microbial degradation of haloaromatics. Ann. Rev. Microbiol. 42: 263–287
Reineke, W & Knackmuss, H-J (1980) Hybrid pathway for chlorobenzoate metabolism in Pseudomonas sp. B13 derivatives. J. Bacteriol. 142: 467–473
Ruisinger, S, Klages, U & Lingens, F (1976) Abbau der 4-Chlorobenzoesaure durch eine Arthrobacterspecies. Arch. Microbiol. 110: 253–256
Safe, SH (1984) Microbial degradation of polychlorinated biphenyls. Microbiol. Ser. 13: 361–369
Sangodkar, UMX, Aldrich, TL, Haugland, RA, Johnson, J, Rothmel, RK, Chapman, PJ & Chakrabarty, AM (1989) Molecular basis of biodegradation of chloroaromatic compounds. Acta Biotechnol. 9: 301–316
Savard, P, Péloquin, L & Sylvestre, M (1990) Cloning of Pseudomonas strain CBS3 Genes Specifying Dehalogenation of 4-Chlorobenzoate. J. Bacteriol. 168: 81–85
Schlömann, M, Fischer, P, Schmidt, E & Knackmuss, H-J (1990) Enzymatic Formation, Stability, and Spontaneous Reactions of 4-Fluoromuconolactone, a Metabolite of the Bacterial Degradation of 4-Fluorobenzoate. J. Bacteriol. 172: 5119–5129
Schmidt, E (1988) Bioconversion of 3-chlorobenzoate to 2-chloromuconate controlled by on line HPLC. Appl. Microbiol. Biotechnol. 27: 347–350
Schmidt, E, Hellwig, M & Knackmuss, H-J (1983) Degradation of chlorophenols by a defined mixed microbial community. Appl. Environ. Microbiol. 46: 1038–1044
Schmidt, E & Knackmuss, H-J (1984) Production of cis, cis-muconate from benzoate and 2-fluoro-cis, cis-muconate from 3-fluorobenzoate by 3-chlorobenzoate degrading bacteria. Appl. Microbiol. Biotechnol. 20: 351–355
Schraa, G, Boone, ML, Jetten, MSM, van Neerven, ARW, Colberg, PJ & Zehnder, AJB (1986) Degradation of 1,4-dichlorobenzene by Alcaligenes sp. strain A175. Appl. Environ. Microbiol. 52: 1374–1381
Schreiber, A, Hellwig, M, Dorn, E, Reineke, W & Knackmuss, H-J (1980) Critical reactions in fluorobenzoic acid degradation by Pseudomonas sp B13. Appl. Environ. Microbiol. 39: 58–67
Schwien, U & Schmidt, E (1982) Improved degradation of monochlorophenols by a constucted strain. Appl. Environ. Microbiol. 44: 33–39
Sharak Genthner, BR, Price II, WA & Pritchard, PH (1989a) Anaerobic degradation of chloroaromatic compounds in aquatic sediments under a variety of enrichment conditions. Appl. Environ. Microbiol. 55: 1466–1471
(1989b) Characterization of anaerobic dechlorinating consortia derived from aquatic sediments. Appl. Environ. Microbiol. 55: 1472–1476
Shelton, DR & Tiedje, JM (1984) Isolation and partial characterization of bacteria in an anaerobic consortium that mineralizes 3-chlorobenzoic acid. Appl. Environ. Microbiol. 48: 840–848
Shiaris, MP & Sayler, GS (1982) Biotransformation of PCBs by natural assemblages of freshwater microorganisms. Environ. Sci. Technol. 16: 367–369
Spain, JC & Nishino, SF (1987) Degradation of 1,4-dichlorobenzene by a Pseudomonas sp. Appl. Environ. Microbiol. 53: 1010–1019
Sperl, GT & Harvey, GJ (1988) Microbial adaptation to bromobenzene in a chemostat. Curr. Microbiol. 17: 99–103
Spokes, JR & Walker, N (1974) Chlorophenol and chlorobenzoic acid co-metabolism by different genera of soil bacterial. Arch. Microbiol. 96: 125–134
Steiert, JG & Crawford, RL (1986) Catabolism of pentachlorophenol by a Flavobacterium bacterium. Biochem. Biophys. Res. Commun. 141: 825–830
Steiert, JG, Pignatello, JJ & Crawford, RL (1987) Degradation of chlorinated phenols by a pentachlorophenol-degrading bacterium. Appl. Environ. Microbiol. 53: 907–910
Stevens, TO, Linkfield, TG & Tiedje, JM (1988) Physiological Characterization of Strain DCB-1, a Unique Sulfidogenic Bacterium. Appl. Environ. Microbiol. 54: 2938–2943
Strubel, V, Rast, HG, Fietz, W, Knackmuss, H-J & Engesser, KH (1989) Enrichment of dibenzofuran utilizing bacteria with high co-metabolic potential towards dibenzodioxin and other anellated aromatics. FEMS Microbiol. Lett. 58: 233–238
Suflita, JM, Robinson, JA & Tiedje, JM (1983) Kinetics of microbial dehalogenation of haloaromatic substrates in methanogenic environments. Appl. Environ. Microbiol. 45: 1466–1473
Sylvestre, M, Mailhiot, K, Ahmad, D & Massé, R (1989) Isolation and preliminary characterization of a 2-chlorobenzoate degrading Pseudomonas. Can. J. Microbiol. 35: 439–443
Sylvestre, M, Massé, R, Ayotte, C, Messier, F & Fauteux, J (1985) Total biodegradation of 4-chlorobiphenyl (4-CB) by a two-membered bacterial culture. Appl. Microbiol. Biotechnol. 21: 192–195
Sylvestre, M, Massé, R, Messier, F, Fauteux, J, Bisaillon, J-G & Beaudet, R (1982) Bacterial nitration of 4-chlorobiphenyl. Appl. Environ. Microbiol. 44: 871–877
Thiele, J, Müller, R & Lingens, F (1987) Initial characterization of 4-chlorobenzoate dehalogenase from Pseudomonas sp. CBS3. FEMS Microbiol. Lett. 41: 115–119
(1988a) Enzymatic dehalogenation of 4-chlorobenzoate by 4-chlorobenzoate dehalogenase from Pseudomonas sp. CBS3 in organic solvents. Appl. Microbiol. Biotechnol. 27: 577–580
(1988b) Enzymatic dehalogenation of chlorinated nitroaromatic compounds. Appl. Environ. Microbiol. 54: 1199–1202
Tiedje, JM & Alexander, M (1969) Enzymatic Cleavage of the Ether Bond of 2,4-Dichlorophenoxyacetate. J. Agric. food Chem. 17: 1080–1084
van den Tweel, WJJ, Ter Burg, N, Kok, JB & De Bont, JAM (1986) Bioformation of 4-hydroxybenzoate from 4-chlorobenzoate by Alcaligenes denitrificans NTB-1. Appl. Microbiol. Biotechnol. 25: 289–294
van den Tweel, WJJ, Kok, JB & De Bont, JAM (1987) Reductive dechlorination of 2,4-dichlorobenzoate to 4-chlorobenzoate and hydrolytic dehalogenation of 4-chloro-, 4-bromo-, and 4-iodobenzoate by Alcaligenes denitrificans NTB-1. Appl. Environ. Microbiol. 53: 810–815
Unterman, R, Bedard, DL, Brennan, MJ, Bopp, LH, Mondello, FJ, Brooks, RE, Mobley, DP, McDermott, JB, Schwartz, CC & Dietrich, DK (1988) Biological approaches for polychlorinated biphenyl degradation. Basic Life Sciences 45: 253–269
Vora, KA, Singh, C & Modi, VV (1988) Degradation of 2-fluorobenzoate by a Pseudomonad. Curr. Microbiol. 17: 249–254
Walia, S, Tewari, R, Brieger, G, Thimm, V & McGuie, T (1988) Biochemical and genetic characterization of soil bacteria degrading polychlorinated biphenyl. In: Abbou, R (Ed) Hazardous Waste: Detection Control Treatment (pp 1621–1632). Elsevier Amsterdam
Walker, N & Harris, D (1970) Metabolism of 3-chlorobenzoic acid by Azotobacter species. Soil Biol. Biochem. 2: 27–32
Watanabe, I (1973) Isolation of pentachlorophenol decomposing bacteria from soil. Soil Sci. Plant Nutr. 19: 109–116
Wyndham, RC & Straus, NA (1988a) Chlorobenzoate catabolism and interaction between Alcaligenes and Pseudomonas species from Bloody Run Creek. Arch. Microbiol. 150: 230–236
Wyndham, RC, Singh, RK & Straus, NA (1988b) Catabolic instability, plasmid gene deletion and recombination in Alcaligenes sp. BR60. Arch. Microbiol. 150: 237–243
You, I-S & Bartha, R (1982) Cometabolism of 3,4-dichloroaniline by Pseudomonas putida. J. Agric. Food Chem. 30: 274–277
Zeyer, J & Kearney, PC (1982a) Microbial degradation of parachloroaniline as sole carbon and nitrogen source. Pesticide Biochem. Physiol. 17: 215–223
(1982b) Microbial metabolism of propanil and 3,4-dichloroaniline. Pesticide Biochem. Physiol. 224: 231-biodegradation
Zeyer, J, Wasserfallen, A & Timmis, KN (1985) Microbial mineralization of ring-substituted anilines through an ortho-cleavage pathway. Appl. Environ. Microbiol. 50: 447–453
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Commandeur, L.C.M., Parsons, J.R. Degradation of halogenated aromatic compounds. Biodegradation 1, 207–220 (1990). https://doi.org/10.1007/BF00058837
Issue Date:
DOI: https://doi.org/10.1007/BF00058837