References
Alexander M (1981) Biodegradation of chemicals of environmental concern. Science 211: 132–138
Armfield SJ, Sallis PJ, Baker PB, Bull AT & Hardman DJ (1995) Biodegradation of haloalkanes byRhodococcus erythropolis Y2: the presence of an oxygenase-type dehalogenase complements a halidohydrolase activity. Biodegradation (in press)
Barth PT, Bolton L & Thomson JC (1992) Cloning and partial sequencing of an operon encoding twoPseudomonas putida haloalkanoate dehalogenases of opposite stereospecificity. J. Bacteriol. 174: 2612–2619
Bouwer EJ, Rittman BE & McCarty PL (1981) Anaerobic degradation of halogenated 1- and 2-carbon organic compounds. Env. Sci. Tech. 15: 596–599
Brokamp A & Schmidt FRJ (1991) Survival ofAlcaligenes xylosoxidans degrading 2,2-dichloropropionate and horizontal transfer of its halidohydrolase gene in a soil microcosm. Curr. Microbiol. 22: 299–306
Bull AT, Hardman DJ & Stubbs BM (1992) Dehalogenation of organohalogen-containing compounds. US Patent P10504.901
Cairus SS (1994) The cloning and analysis ofRhizobium dehalogenase genes. Ph.D. Thesis, University of Leicester, Leicester
Castro CE & Bartnicki EW (1965) Biological cleavage of carbonhalogen bonds in the metabolism of 3-bromopropanol. Biochimica et Biophysica Acta 100: 384–392
—— (1968) Biodehalogenation. Epoxidation of halohydrins, epoxide opening, and transdehalogenation by aFlavobacterium species. Biochemistry 7: 3213–3218
Chang KH, Liang PH, Beck W, Scholten JD & Dunaway-Marino D (1992) Isolation and characterization of the three polypeptide components of 4-chlorobenzoate dehalogenase fromPseudomonas sp. strain CBS-3. Biochemistry 31: 5605–5610
Chaudhry GR & Chapalamadugu S (1991) Biodegradation of halogenated organic compounds. Microbiol. Rev. 55: 59–79
Commandeur LCM & Parsons JR (1994) Biodegradation of halogenated aromatic compounds. In: Ratledge C (Ed) Biochemistry of Microbial Degradation. (pp 423–458) Kluwer Academic Publ. Dordrecht, The Netherlands
Den Dooren Jong LE de (1926) Bijdrage tot de kennis van het mineralisatieproces. Nijgh van Ditmar, Rotterdam
DeWeerd KA, Mandelco L, Tanner RS, Woese CR & Sulflita JM (1990)Desulfomonile tiedjei gen. nov. and sp. nov., a novel anaerobic dehalogenating sulfate-reducing bacterium. Arch. Microbiol. 154: 23–30
Elsner A, Müller R & Lingens F (1991) Separate cloning and expression analysis of two protein components of 4-chlorobenzoate dehalogenase fromPseudomonas sp. CBS3. J. Gen. Microbiol. 137: 477–481
Fathepure BZ & Boyd SA (1988) Dependence of tetrachloroethylene dechlorination on methanogenic substrate consumption byMethanosarcina sp. strain DCM. Appl. Env. Microbiol. 54: 2976–2980
Fathepure BZ & Vogel TM (1991) Complete degradation of poly-chlorinated hydrocarbons by a two-stage biofilm reactor. Appl. Env. Microbiol. 53: 2671–2674
Fogel MM, Taddeo AR & Fogel S (1986) Biodegradation of chlorinated ethanes by a methane-utilizing mixed culture. Appl. Env. Microbiol. 51: 720–724
Franken SM, Rozeboom HJ, Kalk KH & Dijkstra BW (1991) Crystal structure of haloalkane dehalogenase: an enzyme to detoxify halogenated alkanes. EMBO Journal 10: 1297–1302
Gibson SA & Sulflita JM (1990) Anaerobic degradation of 2,4,5-trichlorophenoxyacetic acid in samples from methanogenic aquifer. stimulation by short-chain organic acids and alcohols. Appl Env. Microbiol. 56: 1825–1832
Goldman P, Milne GWA & Keister DB (1968) Carbon-halogen bond cleavage. III. Studies on bacterial halidohydrolases. J. Biol. Chem. 243: 428–434
Häggblom MM & Young LY (1990) Chlorophenol degradation coupled to sulfate reduction. Appl. Env. Microbiol. 56: 3255–3260
Harayama S, Kok M & Neidle EL (1992) Functional and evolutionary relationships among diverse monooxygenases. Ann. Rev. Microbiol. 46: 565–601
Hardman DJ & Slater JH (1981) Dehalogenases in soil bacteria. J. Gen. Microbiol. 123: 117–128
Hardman DJ (1991) Biotransformation of halogenated compounds. Crit. Rev. Biotechnol. 11: 1–40
Higgins IJ, Hammond RC, Sariaslani FS, Best D, Davies MM, Tryhorn SE & Taylor F (1979) Biotransformation of hydrocarbons and related compounds by whole organism suspension of methane-grownMethylosinus trichosporium OB3b. Biochem. Biophys. Res. Comm. 89: 671–677
Horowitz A, Sulflita JM & Tiedje JM (1983) Reductive dehalogenation of halobenzoates by anaerobic lake sediment microorganisms. Appl. Env. Microbiol. 45: 1459–1461
Hughes S (1988) Microbial growth on 3-chloropropionic acid. PhD Thesis University of Wales, Cardiff
Hylckama Vlieg JET & Janssen DB (1991) Bacterial degradation of 3-chloroacrylic acid and the characterization ofcis- andtrans- specific dehalogenases. Biodegradation 2: 25–31
Imai R, Nagata Y, Fukada M, Tagaki M & Yano K (1991) Molecular cloning of aPseudomonas paucimobilis gene encoding a 17-kilodalton polypeptide that eliminates HC1 molecules from γ-hexachlorocyclohexane. J. Bacteriol. 173: 6811–6819
Janssen DB, Gerritse J, Brackman J, Kalk C, Jager D & Witholt B (1988) Purification and characterization of a bacterial dehalogenase with activity toward halogenated alkanes, alcohols and ethers. Eur. J. Biochem. 171: 67–72
Janssen DB, Pries F, Ploeg J van der, Kazemier B, Terpstra P & Witholt B (1989) Cloning of 1,2-dichloroethane degradation genes ofXanthobacter autotrophicus GJ10 and expression and sequencing of thedh1A gene. J. Bacteriol. 171: 6791–6799
—— (1994) Genetics and biochemistry of dehalogenating enzymes. Ann. Rev. Microbiol. 48: 163–191
Jensen HL (1951) Decomposition of chlorosubstituted aliphatic acids by soil bacteria. Can. J. Microbiol. 3: 151–164
—— (1957) Decomposition of chloroorganic acids by fungi. Nature London 180: 1416
—— (1959) Decomposition of chlorine-substituted organic acids by fungi Acta. Agriculturae Scandinavica 9: 421–434
—— (1960) Decomposition of chloroacetates and chloropropionates by bacteria. Acta Agriculturae Scandinavica 10: 83–103
Jones DHA, Barth PT, Byrom D & Thomas CM (1992) Nucleotide sequence of the structural gene encoding a 2-haloalkanoic acid dehalogenase ofPseudomonas putida strain AJ1 and purification of the encoded protein. J. Gen. Microbiol. 138: 675–683
Kasai N, Tsujimura K, Unoura K & Suzuki T (1990) Degradation of 2,3-dichloro-1-propanol byPseudomonas sp. Agric. Biol. Chem. 54: 3185–3190
Kawasaki H, Toyama T, Maeda T, Nishino H & Tonomura K (1994) Cloning and sequence analysis of a plasmid-encoded 2-haloacid dehalogenase gene fromPseudomonas putida no. 109. Biosci. Biotech. Biochem. 58: 160–163
Kawasaki H, Tsuda K, Matsushita I & Tonomura K (1992) Lack of homology between two haloacetate dehalogenase genes encoded on a plasmid fromMoraxella species strain B. J. Gen. Microbiol. 138: 1317–1323
Keuning S, Janssen De Beers & Witholt B (1985) Purification and characterization of hydrolytic haloalkane dehalogenase fromXanthobacter autotrophicus GJ10. J. Bacteriol. 163: 635–639
Knackmuss HJ (1981) Degradation of halogenated and sulfonated hydrocarbons. In: Leisinger T, Hütter R, Cook AM & Nüesch J (Eds) Microbial Degradation of Xenobiotics and Recalcitrant Compounds. (pp 189–212) Academic Press, New York
Kohler-Staub D & Kohler HPE (1989) Microbial degradation of β-chlorinated four-carbon aliphatic acids. J. Bacteriol. 171: 1428–1434
Kohler-Staub D & Leisinger T (1985) Dichloromethane dehalogenase ofHyphomicrobium species strain DM2. J. Bacteriol. 162: 676–681
Kohler-Staub D, Hartmans S, Gälli R, Suter F & Leisinger T (1986) Evidence for identical dichloromethane dehalogenases in different methylotrophic bacteria. J. Gen. Microbiol. 132: 2837–2843
La Roche SD & Leisinger T (1990) Sequence analysis and expression of the bacterial dichloromethane dehalogenase structural gene, a member of the glutathione S-transferase supragene family. J. Bacteriol. 172: 164–171
Leigh JA, Skinner AJ & Cooper RA (1988) Partial purification, stereospecificity and stoichiometry of three dehalogenases from aRhizobium species. FEMS Microbiol. Lett. 49: 353–356
Leisinger T & Bader R (1993) Microbial dehalogenation of synthetic organohalogen compounds: hydrolytic dehalogenases. Chimia 47: 116–121
Little M & Williams PA (1971) A bacterial halidohydrolase. Its purification, some properties and its modification by specific amino acid reagents. Eur. J. Biochem. 21: 99–109
Löffler F, Müller R & Lingens F (1992) Purification and properties of 4-halobenzoate-coenzyme A ligase fromPseudomonas sp. CBS3. Hoppe-Seyler's Zeitschrift für Physiologische Chemie 373: 1001–1007
Morris PJ, Mohn WW, Quensen JF, Tiedje JM & Boyd SA (1992) Establishment of a polychlorinated biphenyl-degrading enrichment culture with predominantlymeta dechlorination. Appl. Env. Microbiol. 58: 3088–3094
Motosugi K, Esaki N & Soda K (1982a) Purification and properties of 2-haloacid dehalogenase fromPseudomonas putida. Agric. Biol. Chem. 46: 837–838
—— (1982b) Bacterial assimilation of D- and L-2-chloropropionates and occurrence of a new dehalogenase. Arch. Microbiol. 131: 179–183
Müller R, Oltmans RH & Lingens F (1988) Enzymic dehalogenation of 4-chlorobenzoate by extracts fromArchrobacter sp. SU DSM 20407. Hoppe-Seyler's Zeitschrift für Physiologische Chemie 369: 567–571
Müller R, Thiele J, Klages U & Lingens F (1984) Incorporation of [18O]-water into 4-hydroxybenzoate dehalogenase fromPseudomonas species CBS3. Biochem. & Biophys. Res. Comm. 124: 178–182
Murdiyatmo U (1991) Molecular genetic analysis of a 2-haloacid halidohydrolase structural gene. PhD Thesis, University of Kent at Canterbury, Canterbury
Murdiyatmo U, Asmara W, Tsang JSH, Baines AJ, Bull AT & Hardman DJ (1992) Molecular biology of the 2-haloacid halidohydrolase fromPseudomonas cepacia MBA4. Biochem. J. 284: 87–93
Nagasawa T, Nakamura T, Yu F, Watanabe I & Yamada H (1992) Purification and characterization of halohydrin hydrogen-halide lyase from a recombinantEscherichia coli containing the gene from aCorynebacterium species. Appl. Microbiol. Biotech. 36: 478–482
Nagata Y, Nariya T, Ohtomo R, Fukuda M, Yano K & Takagi M (1993) Cloning and sequencing of a dehalogenase gene encoding an enzyme with hydrolase activity involved in the degradation of gamma-hexachlorocyclohexane inPseudomonas paucimobilis. J. Bacteriol. 175: 6403–6410
Nakamura T, Nagasawa T, Yu F, Watanabe I & Yamada H (1992) Resolution and some properties of enzymes involved in enantioselective transformation of 1,3-dichloro-2-propanol to (R)-3-chloro-1,2-propanediol byCorynebacterium species strain N-1074. J. Bacteriol. 174: 7613–7619
—— (1994) Characterization of a novel enantioselective halohydrin hydrogen-lyase. Appl. Env. Microbiol. 60: 1297–1301
Nardi-Die V, Kurihara T, Okamura O, Liu JQ, Koshikawa H, Ozaki H, Terashima Y, Esaki N & Soda K (1994) Comparative studies of genes encoding thermostable L-2-halo acid dehalogenase fromPseudomonas species strain YL, other dehalogenases, and two related hypothetical proteins fromEscherichia coli. Appl. Env. Microbiol. 60: 3375–3380
Penfold WJ (1913) The inhibitory selective action on bacteria of bodies related to monochloracetic acid. (A contribution to the theory of cell intoxication.) J. Hygiene 13: 35–48
Peters RA (1952) Lethal synthesis. Proceedings of the Royal Society of London Series B 139: 143–167
Ploeg J van der, Hall G van & Janssen DB (1991) Characterization of the haloacid dehalogenase fromXanthobacter autotrophicus GJ10 and sequencing of thedhlB gene. J. Bacteriol. 173: 7925–7933
Quensen JF, Tiedje JM & Boyd S (1988) Reductive dechlorination of polychlorinated biphenyls by anaerobic microorganisms from sediments. Science 242: 752–754
Reineke W & Knackmuss HJ (1988) Microbial degradation of haloaromatics. Ann. Rev. Microbiol. 42: 263–287
Sallis PJ, Armfield SJ, Bull AT & Hardman DJ (1990) Isolation and characterization of a haloalkane halidohydrolase fromRhodococcus erythropolis Y2. J. Gen. Microbiol. 136: 115–120
Schmitz A, Gartemann KH, Fielder J, Grund E & Eichenlaub R (1992) Cloning and sequence analysis of genes for dehalogenation of 4-chlorobenzoate fromArthrobacter sp. strain SU. Appl. Env. Microbiol. 58: 4068–4071
Schneider B, Müller R, Frank R & Lingens F (1991) Complete nucleotide sequences and comparison of the structural genes of two 2-haloalkanoic acid dehalogenases fromPseudomonas species strain CBS3. J. Bacteriol. 173: 1530–1535
Scholten JD, Chang KH, Babbitt PC, Charest H, Sylvestre M & Dunaway-Marino D (1991) Novel enzymatic hydrolytic dehalogenation of a chlorinated aromatic. Science 253: 182–185
Scholtz R, Leisinger T, Suter F & Cook AM (1987) Characterization of 1-chlorohexane halidohydrolase, a dehalogenase of wide substrate range from anArthrobacter species. J. Bacteriol. 169: 5016–5021
Scholtz R, Messi F, Leisinger T & Cook AM (1988a) Three dehalogenases and physiological restraints in the biodegradation of haloalkanes byArthrobacter species strain HA1. App. Env. Microbiol. 54: 3034–3038
Scholtz R, Wackett LP, Egli C, Cook AM & Leisinger T (1988b) Dichloromethane dehalogenase with improved catalytic activity isolated from a fast-growing dichloromethane-utilizing bacterium. J. Bacteriol. 170: 5698–5704
Slater JH (1994) Microbial dehalogenation of haloaliphatic compounds. In: Ratledge C (Ed) Biochemistry of Microbial Degradation. (pp 379–421) Kluwer Academic Publ., Dordrecht, The Netherlands
Smith JM, Harrison K & Colby J (1990) Purification and characterization of D-2-haloacid dehalogenase fromPseudomonas putida strain AJ1/23. J. Gen. Microbiol. 136: 881–886
Stucki GR, Gälli R, Ebersold HR & Leisinger T (1981) Dehalogenation of dichloromethane by cell extracts ofHyphomicrobium DM2. Arch. Microbiol. 130: 366–371
Topping AW (1992) An investigation into the transposition and dehalogenase functions ofDEH, a mobile genetic element, fromPseudomonas putida strain PP3. PhD Thesis, University of Wales, Cardiff
Verschueren KHG, Franken SM, Rozeboom HJ, Kalk KH & Dijkstra BW (1993a) Refined X-ray structures of haloalkane dehalogenase at pH 6.2 and pH 8.2 and implications for the reaction mechanism. J. Mol. Biol. 232: 856–872
Verschueren KHG, Seljée F, Rozeboom HJ, Kalk KH & Dijkstra BW (1993b) Crystallographic analysis of the catalytic mechanism of haloalkane dehalogenase. Nature, London 363: 693–698
Vogel TM & McCarty PL (1985) Biotransformation of tetrachloroethylene, dichloroethylene, vinylchloride and carbon dioxide under methanogenic conditions. Appl. Env. Microbiol. 49: 1080–1083
Weightman AJ, Weightman AL & Slater JH (1982) Stereospecificity of 2-monochloropropionate dehalogenation by the two dehalogenases ofPseudomonas putida PP3: evidence of two different dehalogenation mechanisms. J. Gen. Microbiol. 128: 1755–1762
—— (1992) Microbial dehalogenation of trichloroacetic acid. World J. Microbiol. Biotechnol. 8: 512–518
Wijngaard AJ van der, Janssen D & Witholt B (1989) Degradation of epichlorohydrin and halohydrins by bacterial cultures isolated from freshwater sediments. J. Gen. Microbiol. 135: 2199–2208
Wijngaard AJ van der, Reuvekamp PTW & Janssen DB (1991) Purification and characterization of haloalcohol dehalogenase fromArthrobacter sp. strain AD2. J. Bacteriol. 173: 124–129
Wijngaard AJ van der, Kamp KWHJ van der, Ploeg J van der, Pries F, Kazemier B & Janssen DB (1992) Degradation of 1,2-dichloroethane byAncylobacter aquaticus and other facultative methylotrophic bacteria. Appl. Env. Microbiol. 58: 976–983
Yokota T, Fuse H, Omori T & Minoda Y (1986) Microbial dehalogenation of haloalkanes by oxygenase or halidohydrolase. Agric. Biol. Chem. 50: 453–460
Yokota T, Omori T & Kodama T (1987) Purification and properties of haloalkane dehalogenase fromCorynebacterium species strain m15-3. J. Bacteriol. 169: 4049–4054
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Slater, J.H., Bull, A.T. & Hardman, D.J. Microbial dehalogenation. Biodegradation 6, 181–189 (1995). https://doi.org/10.1007/BF00700456
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DOI: https://doi.org/10.1007/BF00700456