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Genetics and biochemistry of 1,2-dichloroethane degradation

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Abstract

Dichloroethane (1,2-DCE) is a synthetic compound that is not known to be formed naturally. Nevertheless, several pure microbial cultures are able to use it as a sole carbon source for growth. Degradation of 1,2-DCE proceeds via 2-chloroethanol, chloroacetaldehyde and chloroacetate to glycolate. The genes encoding the enzymes responsible for the conversion of 1,2-DCE to glycolic acid have been isolated. The haloalkane dehalogenase and an aldehyde dehydrogenase are plasmid encoded. Two other enzymes, the alcohol dehydrogenase and the haloacid dehalogenase, are chromosomally encoded. Sequence analysis indicates that the haloacid dehalogenase belongs to the L-specific 2-chloroproprionic acid dehalogenases. From the three-dimensional structure and sequence similarities, the haloalkane dehalogenase appears to be a member of the α/β hydrolase fold hydrolytic enzymes, of which several are involved in the degradation of aromatic and aliphatic xenobiotic compounds.

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References

  • Anthony C & Zatman LJ (1967) The microbial oxidation of methanol. Purification and properties of the alcohol dehydrogenase ofPseudomonas sp. M27. Biochem. J. 104: 953–959

    Google Scholar 

  • Franken SM, Rozeboom HJ, Kalk KH & Dijkstra BW (1991) Crystal structure of haloalkane dehalogenase: an enzyme to detoxify halogenated alkanes. EMBO J. 10: 1297–1302

    Google Scholar 

  • Frantz B, Ngai KL, Chatterjee DK, Ornston LN & Chakrabarty AM (1987) Nucleotide sequence and expression ofclcD, a plasmidborne dienelactone hydrolase gene fromPseudomonas sp. strain B13. J. Bacteriol. 169: 704–709

    Google Scholar 

  • Greer CW, Baumier D & Samson R (1989) Application of on-line sensors during growth of the DCE degrading bacteriumXanthobacter autotrophicus. J. Biotechnol. 12: 261–274

    Google Scholar 

  • Gschwend PM, Macfarlane JK & Newman KA (1985) Volatile halogenated organic compounds released to seawater from temperate marine macroalgae. Science 227: 1033–1035

    Google Scholar 

  • Hardman DJ & Slater JH (1981) Dehalogenases in soil bacteria. J. Gen. Microbiol. 123: 117–128

    Google Scholar 

  • Horn JM, Harayama S & Timmis KN (1991) DNA sequence determination of the TOL plasmid (pWWO)xylGFJ genes ofPseudomonas putida: implications for the evolution of aromatic catabolism. Mol. Microbiol. 5: 2459–2474

    Google Scholar 

  • Janssen DB, Scheper A & Witholt BW (1984) Biodegradation of 2-chloroethanol and 1,2-dichloroethane by pure bacterial cultures. In: Houwink EH & Van der Meer RR (Eds) Innovations in Biotechnology, pp 169–178. Elsevier, Amsterdam

    Google Scholar 

  • Janssen DB, Scheper A, Dijkhuizen L & Witholt B (1985) Degradation of halogenated aliphatic compounds byXanthobacter autotrophicus GJ10. Appl. Environ. Microbiol. 49: 673–677

    Google Scholar 

  • Janssen DB, Keuning S & Witholt B (1987a) Involvement of a quinoprotein alcohol dehydrogenase and an NAD-dependent aldehyde dehydrogenase in 2-chloroethanol metabolism inXanthobacter autotrophicus GJ10. J. Gen. Microbiol. 133: 85–92

    Google Scholar 

  • Janssen DB, Jager D & Witholt B (1987b) Degradation of n-haloalkanes and α,ω-dihaloalkanes by wild-type and mutants ofAcinetobacter sp. strain GJ70. Appl. Environ. Microbiol. 53: 561–566

    Google Scholar 

  • Janssen DB, Pries F, Van der Ploeg J, Kazemier B, Terpstra P & Witholt B (1989) Cloning of 1,2-dichloroethane degradation genes ofXanthobacter autotrophicus GJ10, and expression and sequencing of thedhlA gene. J. Bacteriol. 171: 6791–6799

    Google Scholar 

  • 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

    Google Scholar 

  • Kawasaki H, Tsuda K, Matsushita I & Tonomura K (1992) Lack of homology between two haloacetate dehalogenase genes encoded on a plasmid fromMoraxella sp. strain B. J. Gen. Microbiol. 138: 1317–1323

    Google Scholar 

  • Keuning S, Janssen DB & Witholt B (1985) Purification and characterization of hydrolytic haloalkane dehalogenase fromXanthobacter autotrophicus GJ10. J. Bacteriol. 163: 635–639

    Google Scholar 

  • Kimbara K, Hashimoto T, Fukuda M, Koana T, Takagi M, Oishi M & Yano K (1989) Cloning and sequencing of two tandem genes involved in degradation of 2,3-dihydroxybiphenyl to benzoic acid in the polychlorinated biphenyl-degrading soil bacteriumPseudomonas sp. strain KKS102. J. Bacteriol. 171: 2740–2747

    Google Scholar 

  • La Roche SD & Leisinger T (1991) Identification ofdcmR, the regulatory gene governing expression of dichloromethane dehalogenase inMethylobacterium sp. strain DM4. J. Bacteriol. 173: 6714–6721

    Google Scholar 

  • Menn F-M, Zylstra GJ & Gibson DT (1991) Location and sequence of thetodF gene encoding 2-hydroxy-6-oxohepta-2,4-dienoate hydrolase inPseudomonas putida F1. Gene 104: 91–94

    Google Scholar 

  • Motosugi K & Soda K (1983) Microbial degradation of synthetic organochlorine compounds. Experientia 39: 1214–1220

    Google Scholar 

  • 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

    Google Scholar 

  • Murdiyatmo U, Asmara W, Tsang JSH, Baines AJ, Bull AT & Hardman DJ (1992) Molecular biology of the 2-haloacid halidohydrolase IVa fromPseudomonas cepacia MBA4. Biochem. J. 284: 87–93

    Google Scholar 

  • 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 γ-hexachlorohexane inPseudomonas paucimobilis. J. Bacteriol. 175: 6403–6410

    Google Scholar 

  • Nordlund I & Shingler V (1990) Nucleotide sequence of themeta-cleavage pathway enzymes 2-hydroxymuconic semialdehyde dehydrogenase and 2-hydroxymuconic semialdehyde hydrolase fromPseudomonas CF600. Biochim. Biophys. Acta 1049: 227–230

    Google Scholar 

  • Ollis DL, Cheah E, Cygler M, Dijkstra BW, Frolow F, Franken SM, Harel M, Remington SJ, Silman I, Schrag J, Sussman JL, Verschueren KHG & Goldman A (1992) The α/β hydrolase fold. Prot. Engin. 5: 197–211

    Google Scholar 

  • Perkins EJ, Gordon MP, Caceres O & Lurquin PF (1992) Organization and sequence analysis of the 2,4-dichlorophenol hydroxylase and dichlorocatechol oxidative operons of plasmid pJP4. J. Bacteriol. 172: 2351–2359

    Google Scholar 

  • Pries F, Kingma J, Pentenga M, van Pouderoyen G, Jeronimus-Stratingh CM, Bruins AP & Janssen DB. (1994a) Site-directed mutagenesis and oxygen isotope incorporation studies of the nucleophilic aspartate of haloalkane dehalogenase. Biochemistry. 33: 1242–1247

    Google Scholar 

  • Pries F, van den Wijngaard AJ, Bos R, Pentenga M & Janssen DB (1994b). The role of spontaneous cap domain mutations in haloalkane dehalogenase specificity and evolution. J. Biol. Chem. 269: 17490–17494

    Google Scholar 

  • Pries F, Van der Ploeg JR, Dolfing J & Janssen DB. (1994c) Microbial degradation of halogenated aliphatic compounds: the role of adaptation. FEMS Microbiol. Rev., in press

  • Schanstra JP, Rink R, Pries F & Janssen DB (1993) Construction of an expression and site-directed mutagenesis system of haloalkane dehalogenase inEscherichia coli. Prot. Expr. Purif. 4: 479–489

    Google Scholar 

  • 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 sp. strain CBS3. J. Bacteriol. 173: 1530–1535

    Google Scholar 

  • Scholtz R, Schmuckle A, Cook AM & Leisinger T (1987) Degradation of eighteen 1-monohaloalkanes byArthrobacter sp. strain HA1. J. Gen. Microbiol. 133: 267–274

    Google Scholar 

  • Slater JH, Weightman AJ & Hall BG (1985) Dehalogenase genes ofPseudomonas putida PP3 on chromosomally located transposable elements. Mol. Biol. Evol. 2: 557–567

    Google Scholar 

  • Stroeher UH, Karageorgos LE, Morona R & Manning PA (1992) Serotype conversion inVibrio cholerae O1. Proc. Natl. Acad. Sci. USA 89: 2566–2570

    Google Scholar 

  • Strotmann UJ, Pentenga M & Janssen DB (1990) Degradation of 2-chloroethanol by wild type and mutants ofPseudomonas putida US2. Arch. Microbiol. 154: 294–300

    Google Scholar 

  • Stucki G & Leisinger T (1983a) Bacterial degradation of 2-chloroethanol proceeds via 2-chloroacetic acid. FEMS Microbiol. Lett. 16: 123–126

    Google Scholar 

  • Stucki G, Krebser U & Leisinger T (1983b) Bacterial growth on 1,2-dichloroethane. Experientia 39: 1271–1273

    Google Scholar 

  • Stucki G, Thuer M & Bentz R (1992) Biological degradation of 1,2-dichloroethane under groundwater conditions. Water Res. 26: 273–278

    Google Scholar 

  • Tardif G, Greer CW, Labbé D & Lau PCK (1991) Involvement of a large plasmid in the degradation of 1,2-dichloroethane byXanthobacter autotrophicus GJ10. Appl. Environ. Microbiol. 57: 1853–1857

    Google Scholar 

  • Thomas AW, Lewington J, Hope S, Topping AW, Weightman AJ & Slater JH (1992) Environmentally directed mutations in the dehalogenase system ofPseudomonas putida strain PP3. Arch. Microbiol. 158: 176–182

    Google Scholar 

  • Van den Wijngaard AJ, van der Kamp K, van der Ploeg J, Kazemier B, Pries F & Janssen DB (1992) Degradation of 1,2-dichloroethane by facultative methylotrophic bacteria. Appl. Environ. Microbiol. 58: 976–983

    Google Scholar 

  • Van den Wijngaard AJ, Prins J, Smal AJAC & Janssen DB (1993a) Microbial growth on 2-chloroethylvinylether byAncylobacter aquaticus AD25 and AD27. Appl. Environ. Microbiol. 59: 2777–2783

    Google Scholar 

  • Van den Wijngaard AJ, Wind RD & Janssen DB (1993b) Kinetics of bacterial growth on chlorinated aliphatic compounds. Appl. Environ. Microbiol. 59: 2041–2048

    Google Scholar 

  • Van der Meer JR, Eggen RI, Zehnder AJ & de Vos WM (1991) Sequence analysis of thePseudomonas sp strain P51tcb gene cluster, which encodes metabolism of chlorinated catechols: evidence for specialization of catechol 1,2-dioxygenases for chlorinated substrates. J. Bacteriol. 173: 2425–2434

    Google Scholar 

  • Van der Meer JR, de Vos WM, Harayama S & Zehnder AJB (1992) Molecular mechanisms of genetic adaptation to xenobiotic compounds. Microbiol. Rev. 56: 677–694

    Google Scholar 

  • Van der Ploeg JR, Van Hall G & Janssen DB (1991) Characterization of the haloacid dehalogenase fromXanthobacter autotrophicus GJ10 and sequencing of thedhlB gene. J. Bacteriol. 173: 7925–7933

    Google Scholar 

  • Van der Ploeg JR, Smidt MP, Landa AS & Janssen DB (1994). Identification of chloroacetaldehyde dehydrogenase involved in 1,2-dichloroethane degradation. Appl. Environ. Microbiol. 60: 1599–1605

    Google Scholar 

  • Verschueren KHG, Kingma J, Rozeboom HJ, Kalk KH, Janssen DB & Dijkstra BW (1993a) Crystallographic and fluorescence studies of the interaction of haloalkane dehalogenase with halide ions. Studies with halide compounds reveal a halide binding site in the active site. Biochemistry 32: 9031–9037

    Google Scholar 

  • Vershueren KHG, Seljée F, Rozeboom HJ, Kalk KH, Dijkstra BW (1993b) Crystallographic analysis of the catalytic mechanism of haloalkane dehalogenase. Nature 363: 693–698

    Google Scholar 

  • Zhao S, Sandt CH, Feulner G, Vlazny DA, Gray JA & Hill CW (1993)Rhs elements ofEscherichia coli K-12: complex composites of shared and unique components that have different evolutionary histories. J. Bacteriol. 175: 2799–2808

    Google Scholar 

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  1. Department of Biochemistry, University of Groningen, 9747 AG, Groningen, The Netherlands

    Dick B. Janssen, Jan R. van der Ploeg & Frens Pries

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  1. Dick B. Janssen
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  2. Jan R. van der Ploeg
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  3. Frens Pries
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Janssen, D.B., van der Ploeg, J.R. & Pries, F. Genetics and biochemistry of 1,2-dichloroethane degradation. Biodegradation 5, 249–257 (1994). https://doi.org/10.1007/BF00696463

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  • DOI: https://doi.org/10.1007/BF00696463

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