Abstract
Halogenated alkanes constitute a significant group among the organic pollutants of environmental concern. Their industrial and agricultural uses are extensive, but until 1978 they were considered to be non-biodegradable. In recent years, microorganisms were described that could degrade, partially or fully, singly or in consortia, many of the compounds tested. The first step in haloalkane degradation appears to be universal: removal of the halogen atom(s). This is mediated by a group of enzymes, generally known as dehalogenases, acting in most cases either as halidohydrolases or oxygenases. Nevertheless, information is still severely lacking regarding the biochemical pathways involved in these processes, as well as their genetic control.
A recently isolated Pseudomonas strain, named ES-2, was shown to possess a very wide degradative spectrum, and to contain at least one hydrolytic dehalogenase. The utilization by this organism of water-insoluble haloalkanes, such as 1-bromooctane, appears to consist of three phases: extracellular emulsification by a constitutively excreted surface active agent, periplasmic dehalogenation by an inducible dehalogenase, and intracellular degradation of the residual carbon skeleton.
Similar content being viewed by others
References
Alexander M (1981) Biodegradation of chemicals of environmental concern. Science 211: 132–38
Alexander M (1985) Biodegradation of organic chemicals. Environ. Sci. Technol. 19: 106–111
Baldauf G (1981) Der Fall Grenzach—Beispiel einer Grundwasserverschmutzung mit umweltrelevanten Stoffen. In: Halogenkohlenwasserstoffe in Grundwassern. DVGW-Schriftenreihe. Wasser Nr. 29, Frankfurt.
Bouwer EJ & McCarty PL (1983a) Transformations of 1- and 2-carbon halogenated aliphatic organic compounds under methanogenic conditions. Appl. Environ. Microbiol. 4: 1286–1294
Bouwer EJ & McCarty PL (1983b) Transformations of halogenated organic compounds under denitrification conditions. Appl. Environ. Microbiol. 45: 1295–1299
Brunner W, Staub D & Leisinger T (1980) Bacterial degradation of dichloromethane. Appl. Environ. Microbiol. 40: 950–958
Castro CE & Belser NO (1968) Biodehalogenation. Reductive dehalogenation of the biocides ethylene dibromide, 1,2-dibromo-3-chloropropane, and 2,3-dibromobutane in soil. Environ. Sci. Technol. 2: 779–783
Chaudhry GR & Chapalamadugu S (1991) Biodegradation of halogenated organic compounds. Microbiol. Rev. 55: 59–79
Dalton H & Stirling DI (1982) Co-metabolism. Phil. Trans. R. Soc. Lond. B. 297: 481–496
Edwards PR, Campbell I & Milne GS (1982) The impact of chloromethanes on the environment. Part 2: methyl chloride and methylene chloride. (pp 619–622) Chem. Ind. Lond.
Ghosal D, You I-S, Chatterjee DK & Chakrabarty AM (1985) Microbial degradation of halogenated compounds. Science 228: 135–142
Gschwend PM, MacFarlane JK & Newman KA (1985) Volatile halogenated organic compounds released to seawater from temperate marine microalgae. Science 227: 1033–1035
Hardman DJ, Gowland PC & Slaater JH (1986) Plasmids from soil bacteria enriched on halogenated alkanoic acids. Appl. Environ. Microbiol. 51: 44–51
f09Hartmans S, Schmuckle A, Cook AM & Leisinger T (1986) Methyl chloride: naturally occurring toxicant and C-1 growth substrate. J. Gen Microbiol. 132: 1139–1142
Janssen DB, Scheper A, Dijkhuizen L & Witholt B (1985) Degradation of halogenatedc aliphatic compounds byXanthobacter autotrophicus GJ10. Appl. Enviro. Microbiol. 49: 673–677
Janssen DB, Jager D & Witholt B (1987) Degradation of n-haloalkanes and alpha, omega-dihaloalkanes by wild-type and mutants of Acinetobacter sp. strain GJ70. Appl. Environ. Microbiol. 539: 561–566
Jensen HL (1960) Decomposition of chloroacetate by bacteria. Acta. Agric. Scand. 10: 83–103
Kawasaki H, Yahara H & Tonomura K (1981) Isolation and characterization of plasmid PU-01 mediating dehalogenation of haloacetate and mercury resistance in Morasella sp. Agric Biol. Chem. 45: 1477–1482
Keuning S, Janssen DB & Witholt B (1985) Purification and characterization of hydrolytic haloalkane dehalogenase from Xanthobacter autotrophicus GJ10. J. Bacteriol. 163: 635–639
Knackmuss H-J (1981) Degradation of halogenated and sulfonated hydrocarbons. In: Leisinger T, Cook AM, Hutter R & Neusch J (Eds) Microbial Degradation of Xenobiotics and Recalcitrant Compounds (pp 189–212). Academic Press, London
Kobayashi H & Rittmann BE (1982) Microbial removal of hazardous organic compounds. Environ. Sci. Technol. 16: 170A-183A
Kohler-Stabu D & Leisinger T (1985) Dichloromethane dehalogenase of Hyphomicrobium sp. strain DM2. Bacteriol. 162: 676–681
Lal R & Saxena DM (1982) Accumulation, metabolism, and effects of organochlorine insecticides on microorganisms. Microbiol. Rev. 46: 95–127
Leisinger T (1983) Microorganisms and xenobiotic compounds. Experientia 39: 1183–1191
Little CD, Palumbo AV, Herbes SE, Lidstrom ME, Tyndall RL & Gilmer PJ (1988) Trichloroethylene biodegradation by a methane-oxidizing bacterium. Appl. Environ. Microbiol. 54: 951–956
Lovelock JE (1975) Natural halocarbons in the air and in the sea. Nature 256: 193–194
Morgan P & Watkinson RJ (1989) Microbiological methods for the cleanup of soil and ground water contaminated with halogenated organic compounds. FEMS Microbiol. Rev. 63: 277–300
Motosugi K & Soda K (1983) Microbial degradation of synthetic organochlorine compounds. Experientia 39: 1214–1220
Motosugi K, Esaki N & Soda K (1982) Purification and properties of a new enzyme, DL-2-haloacid dehalogenase, from Pseudomonas sp. J. Bacteriol. 150: 522–527
Murphy GL & Perry JJ (1983) Incorporation of chlorinated alkanes into fatty acids of hydrocarbon-utilizing mycobacteria. J. Bacteriol. 156: 1158–1164
Oldenhuis R, Vink RLJM, Janssen DB & Witholt B (1989) Degradation of chlorinated aliphatic hydrocarbons by Methylosinus trichosporium OB3b expressing soluble methane monooxygenase. Appl. Environm. Microbiol. 55: 2819–2826
Omori T & Alexander M (1978a) Bacterial and spontaneous dehalogenation of organic compounds. Appl. Environ. Microbiol. 35: 512–516
Omori T & Alexander M (1978b) Bacterial dehalogenation of halogenated alkanes and fatty acids. Appl. Environ. Microbiol. 35: 867–871
Omori T, Kimura T & Kodama T (1987) Bacterial cometabolic degradation of chlorinated paraffins. Appl. Microbiol. Biotechnol. 25: 553–557
Pearson CR (1982) C1 and C2 halocarbons. In: Hutzinger O (Ed) The Handbook of Environmental Chemistry, Vol 3, Part B (pp 69–88). Springer-Verlag, Berlin, Heidelberg, New York
Perry JJ (1979) Microbial cooxidations involving hydrocarbons. Microbiol. Rev. 43: 59–72
Pignatello JJ (1986) Ethylene dibromide mineralization in soils under aerobic conditions. Appl. Environ. Microbiol. 51: 588–592
Rasche ME, Hyman MR & Arp DJ (1990) Biodegradation of halogenated hydrocarbon fumigants by nitrifying bacteria. Appl. Environ. Microbiol. 56: 2568–2571
Reineke W & Knackmuss H-J (1988) Microbial degradation of haloaromatics. Annu. Rev. Microbiol. 42: 263–287
Rosenberg E (1986) Microbial surfactants. CRC Crit. Revs. Biotechnol. 3: 109–132
Rosenberg E, Zuckerberg A, Rubinovitz C & Gutnick DL (1979) Emulsifier of Arthrobacter RAG-1: isolation and emulsifying properties. Appl. Environ. Microbiol. 37: 402–408
Sar N & Rosenberg E (1983) Emulsifier production by Acinetobacter calcoaceticus strains. Curr. Microbiol. 9: 309–314
Sar N & Rosenberg E (1989) Colonial differentiation and hydrophobicity of a Vibrio sp. Curr. Microbiol. 18: 331–334
Scholtz R, Scmuckle A, Cook AM & Leisinger T (1987a) Degradation of eighteen 1-monohaloalkanes by Arthrobacter sp. strain HA1. J. Gen. Microbiol. 133: 267–273
Scholtz R, Leisinger T, Suter F & Cook AM (1987b) Characterization of 1-chlorohexane halidohydrolase, a dehalogenase of wide substrate range from an Arthrobacter sp. J. Bacteriol. 169: 5016–5021
Scholtz R, Messi F, Leisinger T & Cook AM (1988) Three dehalogenases and physiological restraints in the biodegradation of haloalkanes by Arthrobacter sp. strain HA1. Appl. Environm. Microbiol. 54: 3034–3038
Slater JH & Bull AT (1982) Environmental microbiology: biodegradation. Phil. Trans. R. Soc. Lond. B. 297: 575–597
Slater H, Lovatt D, Weightman AJ, Senior E & Bull AT (1979) The growth of Pseudomonas putida on chlorinated aliphatic acids and its dehalogenase activity. J. Gen. Microbiol. 114: 125–136
Stucki G, Galli R, Ebersold H-R & Leisinger T (1981) Dehalogenation of dichloromethane by cell extracts of Hyophomicrobium DM2. Arch. Microbiol. 130: 366–371
Stucki G, Krebser U & Leisinger T. (1983) Bacterial growth on 1,2-dichloroethane. Experientia 39: 1271–1273
Swindoll CM, Aelion CM & Pfaender FK (1988) Influence of inorganic and organic nutrients on aerobic biodegradation and on the adaptation response of subsurface microbial communities. Appl. Environ. Microbiol. 54: 212–217
Tsang JSH, Sallis PJ, Bull AT & Hardman DJ (1988) A monobromoacetate dehalogenase from Pseudomonas cepacia MBA4. Arch. Microbiol. 150: 441–446
Vandenbergh PA & Kunka BS (1988) Metabolism of volatile chlorinated aliphatic hydrocarbons by Pseudomonas fluorescens. Appl. Environ. Microbiol. 54: 2578–2579
Veissmann M & Hammer MJ (1985) Water Supply and Pollution Control, 4th edition. Harper & Row, New York.
Vogel TM & McCarty PL (1987) Abiotic and biotic transformations of 1,1,1-trichloroethane under methanogenic conditions. Environ. Sci. Technol. 21: 1208–1213
Vogel TM, Criddle CS & McCarty PL (1987) Transformations of halogenated aliphatic compounds. Environ. Sci. Technol. 21: 722–736
Werner P (1989) Experiences in the use of microorganisms in soil and aquifer decontamination. In: Kobus & Kinzelbach (Eds) Contaminant Transport in Groundwater (pp 59–63). Balkema, Rotterdam
Yokota T, Fuse H, Omori T & Minoda Y (1986) Microbial dehalogenation of haloalkanes mediated by oxygenase or halohydrolase. Agric. Biol. Chem. 5: 453–460
Yokota T, Omori T & Kodam T (1987) Purification and properties of haloalkane dehalogenase from Corynebacterium sp. strain m15–3. J. Bacteriol. 169: 4049–4054
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Belkin, S. Biodegradation of haloalkanes. Biodegradation 3, 299–313 (1992). https://doi.org/10.1007/BF00129090
Issue Date:
DOI: https://doi.org/10.1007/BF00129090