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References

  • 1
    Streitwieser, A. and Heathcock, C.H. (1980) Organische Chemie. Verlag Chemie, Weinheim.
  • 2
    Morrison, R.T. and Boyd, R.N. (1986) Lehrbuch der organischen Chemie. VCH, Weinheim.
  • 3
    Pine, S.H. (1987) Organic Chemistry. McGraw-Hill, New York.
  • 4
    March, J. (1992) Advanced Organic Chemistry: Reactions, Mechanisms and Structure. John Wiley and Sons, New York.
  • 5
    Dennis, M. and Kolattukudy, P.E. (1992) A cobalt-porphyrin enzyme converts a fatty aldehyde to a hydrocarbon and CO. Proc. Natl. Acad. Sci. USA 89, 53065310.
  • 6
    Fukuda, H., Ogawa, T. and Tanase, S. (1993) Ethylene production by microorganisms. Adv. Microb. Physiol. 35, 275306.
  • 7
    Cheesbrough, T.M. and Kolattukudy, P.E. (1988) Microsomal preparation from an animal tissue catalyzes release of carbon monoxide from a fatty aldehyde to generate an alkane. J. Biol. Chem. 263, 27382743.
  • 8
    Görgen, G. and Boland, W. (1989) Biosynthesis of 1-alkenes in higher plants: stereochemical implications: a model study with Carthamus tinctorius (Asteraceae). Eur. J. Biochem. 185, 237242.
  • 9
    Reed, J.R., Vanderwel, D., Choi, S., Pomonis, J.G., Reitz, R.C., Blomquist, G.J. (1994) Unusual mechanism of hydrocarbon formation in the housefly: cytochrome P450 converts aldehyde to the sex pheromone component (Z)-9-tricosene and CO2. Proc. Natl. Acad. Sci. USA, 91, 1000010004.
  • 10
    Calvin, M. (1980) Hydrocarbons from plants: analytical methods and observations. Naturwissenschaft 67, 525533.
  • 11
    Jüttner, F. and Henatsch, J.J. (1986) Anoxic hypolimnion is a significant source of biogenic toluene. Nature 323, 797799.
  • 12
    Pons, J.L., Rimbault, A., Darbord, J.C. and Leluan, G. (1984) Biosynthèse de toluene chez Clostridium aerofoetidum souche WS. Ann. Microbiol. (Inst. Pasteur) 135B, 219–222.
  • 13
    Fischer-Romero, C., Tindall, B.J. and Jüttner, F. (1996) Tolumonas auensis gen. nov., sp. nov., a toluene-producing bacterium from anoxic sediments of a freshwater lake. Int. J. Syst. Bacteriol. 46, 183188.
  • 14
    Chen, J., Henderson, G., Grimm, C.C., Lloyd, S.W. and Laine, R.A. (1998) Termites fumigate their nests with naphthalene. Nature 392, 558559.
  • 15
    Harwood, C.S. and Parales, R.E. (1996) The β-ketoadipate pathway and the biology of self-identity. Annu. Rev. Microbiol. 50, 553590.
  • 16
    Dolfing, J., Zeyer, P., Binder-Eicher, P. and Schwarzenbach, R.P. (1990) Isolation and characterisation of a bacterium that mineralises toluene in the absence of molecular oxygen. Arch. Microbiol. 154, 336341.
  • 17
    Altenschmidt, U. and Fuchs, G. (1991) Anaerobic degradation of toluene in denitrifying Pseudomonas sp.: indication of toluene methylhydroxylation and benzoyl-CoA as central aromatic intermediate. Arch. Microbiol. 156, 152158.
  • 18
    Schocher, R.J., Seyfried, B., Vazquez, F. and Zeyer, J. (1991) Anaerobic degradation of toluene by pure cultures of denitrifying bacteria. Arch. Microbiol. 157, 712.
  • 19
    Evans, P.J., Mang, D.T., Kim, K.S. and Young, L.Y. (1991) Anaerobic degradation of toluene by a denitrifying bacterium. Appl. Environ. Microbiol. 57, 11391145.
  • 20
    Fries, M.R., Zhou, J., Chee-Sanford, J. and Tiedje, J.M. (1994) Isolation, characterisation and distribution of denitrifying toluene-degraders from a variety of habitats. Appl. Environ. Microbiol. 60, 28012810.
  • 21
    Rabus, R. and Widdel, F. (1995) Anaerobic degradation of ethylbenzene and other aromatic hydrocarbons by new denitrifying bacteria. Arch. Microbiol. 163, 96103.
  • 22
    Ball, H.D., Johnson, H.A., Reinhard, M. and Spormann, A.M. (1996) Initial reactions in anaerobic ethylbenzene oxidation by a denitrifying bacterium, strain EB1. J. Bacteriol. 178, 57555761.
  • 23
    Harms, G., Rabus, R. and Widdel, F. (1998) Anaerobic oxidation of the aromatic hydrocarbon, p-isopropyltoluene (p-cymene) by two new types of denitrifying bacteria. Arch. Microbiol., in press.
  • 24
    Biegert, T., Fuchs, G. and Heider, J. (1996) Evidence that oxidation of toluene in the denitrifying bacterium Thauera aromatica is initiated by formation of benzylsuccinate from toluene and fumarate. Eur. J. Biochem. 238, 661668.
  • 25
    Lovley, D.R. and Lonergan, D.J. (1990) Anaerobic oxidation of toluene, phenol and p-cresol by the dissimilatory iron reducing organism GS-15. Appl. Environ. Microbiol. 56, 18581864.
  • 26
    Lovley, D.R., Woodward, J.C. and, Chapelle, F.H. (1995) Stimulated anoxic biodegradation of aromatic hydrocarbons using Fe(III) ligands. Nature 370, 128131.
  • 27
    Lovley, D.R., Woodward, J.C. and Chapelle, F.H. (1996) Rapid anaerobic benzene oxidation with a variety of chelated Fe(III) forms. Appl. Environ. Microbiol. 62, 288291.
  • 28
    Langenhoff, A.A.M., Nijenhuis, I., Tan, N.C.G., Briglia, M., Zehnder, A.J.B. and Schraa, G. (1997) Characterisation of a manganese-reducing, toluene-degrading enrichment culture. FEMS Microbiol. Ecol. 24, 113125.
  • 29
    Aeckersberg, F., Bak, F. and Widdel, F. (1991) Anaerobic oxidation of saturated hydrocarbons to CO2 by a new type of sulfate-reducing bacterium. Arch. Microbiol. 156, 514.
  • 30
    Aeckersberg, F., Rainey, F.A. and Widdel, F. (1998) Growth, natural relationships, cell fatty acids and metabolic adaptation of sulfate-reducing bacteria utilising long-chain alkanes under anoxic conditions. Arch. Microbiol., 170, 361369.
  • 31
    Rueter, P., Rabus, R. Wilkes, H., Aeckersberg, F., Rainey, F.A., Jannasch, H.W. and Widdel, F. (1994) Anaerobic oxidation of hydrocarbons in crude oil by denitrifying bacteria. Nature 372, 455458.
  • 32
    Rabus, R., Nordhaus, R., Ludwig, W. and Widdel, F. (1993) Complete oxidation of toluene under strictly anaerobic conditions by a new sulfate-reducing bacterium. Appl. Environ. Microbiol. 59, 14441451.
  • 33
    Beller, H.R., Spormann, A.M., Sharma, P.K., Cole, J.R. and Reinhard, M. (1996) Isolation and characterisation of a novel toluene-degrading sulfate-reducing bacterium. Appl. Environ. Microbiol. 62, 11881196.
  • 34
    Harms, G., Zengler, K., Aeckersberg, F., Minz, D., Rosselló-Mora, R., Rabus, R. and Widdel, F. (1998) Anaerobic oxidation of o-xylene, m-xylene, and homologous alkylbenzenes by new types of sulfate-reducing bacteria. Appl. Environ. Microbiol. (in press).
  • 35
    Lovley, D.R., Coates, J.D., Woodward, J.C. and Phillips, E.J.P. (1995) Benzene oxidation coupled to sulfate reduction. Appl. Environ. Microbiol. 61, 953958.
  • 36
    Coates, J.D., Anderson, R.T. and Lovley, D.R. (1996) Oxidation of polycyclic aromatic hydrocarbons under sulfate-reducing conditions. Appl. Environ. Microbiol. 62, 10991101.
  • 37
    Vogel, T.M. and Grbic-Galic, D. (1986) Incorporation of oxygen from water into toluene and benzene during anaerobic fermentative transformation. Appl. Environ. Microbiol. 52, 200202.
  • 38
    Edwards, E.A. and Grbic-Galic, D. (1994) Anaerobic degradation of toluene and o-xylene by a methanogenic consortium. Appl. Environ. Microbiol. 60, 313322.
  • 39
    Kuhn, E.P., Colberg, P.J., Schnoor, J.L., Wanner, O., Zehnder, A.J.B. and Schwarzenbach, R.P. (1985) Microbial transformations of substituted benzenes during infiltration of river water to groundwater: laboratory column studies. Environ. Sci. Technol. 19, 961968.
  • 40
    Wilson, B.H., Smith, G.B., Rees, J.F. (1986) Biotransformations of selected alkylbenzenes and halogenated aliphatic hydrocarbons in methanogenic aquifer material: a microcosm study. Environ. Sci. Technol. 20, 9971002.
  • 41
    Rabus, R., Fukui, M., Wilkes, H. and Widdel, F. (1996) Degradative capacities and 16S rRNA-targeted whole-cell hybridisation of sulfate-reducing bacteria in an anaerobic enrichment culture utilising alkylbenzenes from crude oil. Appl. Environ. Microbiol. 62, 36053613.
  • 42
    Anders, A., Kaetzke, A., Kämpfer, P., Ludwig, W. and Fuchs, G. (1995) Taxonomic position of aromatic degrading denitrifying pseudomonad strains K172 and KB740 and their description as new members of the genera Thauera, T. aromatica sp. nov., and Azoarcus, A. evansii sp. nov., respectively, members of the beta subclass of Proteobacteria. Int. J. Syst. Bacteriol. 45, 327333.
  • 43
    Beller, H.R., Grbic-Galic, D. and Reinhard, M. (1992) Metabolic by-products of anaerobic toluene degradation by sulfate-reducing enrichment cultures. Appl. Environ. Microbiol. 58, 31923195.
  • 44
    Evans, P.J., Ling, W., Goldschmidt, B., Ritter, E.R. and Young, L.Y. (1992) Metabolites formed during anaerobic transformations of toluene and o-xylene and their proposed relationship to the initial steps of toluene mineralisation. Appl. Environ. Microbiol. 58, 496501.
  • 45
    Seyfried, B., Glod, G., Schocher, R., Tschech, A. and Zeyer, J. (1994) Anaerobic degradation of toluene by pure cultures of denitrifying bacteria. Appl. Environ. Microbiol. 60, 40474052.
  • 46
    Chee-Sanford, J.C., Frost, J.W., Fries, M.R., Zhou, J. and Tiedje, J.M. (1996) Evidence for acetyl-coenzyme A and cinnamoyl-coenzyme A in the anaerobic mineralisation pathway in Azoarcus tolulyticus Tol-4. Appl. Environ. Microbiol. 62, 964973.
  • 47
    Beller, H.R. and Spormann, A.M. (1997) Anaerobic activation of toluene and o-xylene by addition to fumarate in denitrifying strain T. J. Bacteriol. 179, 670676.
  • 48
    Beller, H.R. and Spormann, A.M. (1998) Analysis of the novel benzylsuccinate synthase reaction for anaerobic toluene activation based on structural studies of the product. J. Bacteriol. 180, 54545457.
  • 49
    Beller, H.R., Spormann, A.M. (1997) Benzylsuccinate formation as a means of anaerobic toluene activation by sulfate-reducing strain PRTOL1. Appl. Environ. Microbiol. 63, 37293731.
  • 50
    Rabus, R. and Heider, J. (1998) Initial reactions of anaerobic metabolism of alkylbenzenes in denitrifying and sulfate-reducing bacteria. Arch. Microbiol. 170, 337384.
  • 51
    Gibson, D.T. and Subramanian, V. (1984) Microbial degradation of aromatic hydrocarbons. In: Microbial Degradation of Organic Compounds (Gibson, D.T., Ed.), pp. 181–252. Marcel Dekker, New York.
  • 52
    Harayama, S. and Timmis, K.N. (1990) Catabolism of aromatic hydrocarbons by Pseudomonas, In: Genetics of Bacterial Diversity (Hopwood, D. and Chater, K., Eds.), pp. 151–174. Academic press, London.
  • 53
    Abeles, R.H., Frey, P.A. and Jencks, W.P. (1992) Biochemistry. Jones and Bartlett Publishers, Boston.
  • 54
    Leuthner, B., Leutwein, C., Schulz, H., Hörth, P., Haehnel, W., Schiltz, E., Schägger, H. and Heider, J. (1998) Biochemical and genetic characterisation of benzylsuccinate synthase from Thauera aromatica: a new glycyl radical enzyme catalysing the first step in anaerobic toluene metabolism. Mol. Microbiol. 28, 615628.
  • 55
    Knappe, J. and Sawers, G. (1990) A radical-chemical route to acetyl-CoA: the anaerobically induced pyruvate formate-lyase system of Escherichia coli. FEMS Micobiol. Rev. 75, 383398.
  • 56
    Kessler, D. and Knappe, J. (1996) Anaerobic dissimilation of pyruvate, In: Escherichia coli and Salmonella (Neidhardt, F.C., Ed.), pp. 199–205. ASM Press, Washington.
  • 57
    Coschigano, P.W., Wehrman, T.S. and Young, L.Y. (1998) Identification and analysis of genes involved in anaerobic toluene metabolism by strain T1: putative role of a glycine free radical. Appl. Environ. Microbiol. 64, 16501656.
  • 58
    Wagner, A.F.V., Frey, M., Neugebauer, F.A., Schäfer, W. and Knappe, J. (1992) The free radical in pyruvate formate lyase is located on glycine-734. Proc. Natl. Acad. Sci. USA 89, 9961000.
  • 59
    Knappe, J., Elbert, S., Frey, M. and Wagner, A.F.V. (1993) Pyruvate formate lyase mechanism involving the protein-based glycyl-radical. Biochem. Soc. Trans. 21, 731734.
  • 60
    Coschigano, P.W. and Young, L.Y. (1997) Identification and sequence analysis of two regulatory genes involved in anaerobic toluene metabolism by strain T1. Appl. Environ. Microbiol. 63, 652660.
  • 61
    Platen, H. and Schink, B. (1989) Anaerobic degradation of acetone and higher ketones via carboxylation by newly isolated denitrifying bacteria. J. Gen. Microbiol. 135, 883891.
  • 62
    Ensign, S.A., Small, F.J., Allen, J.R. and Sluis, M.K. (1998) New roles for CO2 in the microbial metabolism of aliphatic epoxides and ketones. Arch. Microbiol. 169, 179187.
  • 63
    Heider, J., Boll, M., Breese, K., Breinig, S., Ebenau-Jehle, C., Feil, U., Gad'on, N., Laempe, D., Leuthner, B., Mohamed, M., Schneider, S., Burchhardt, G. and Fuchs, G. (1998) Differential induction of enzymes involved in anaerobic metabolism of aromatic compounds in the denitrifying bacterium Thauera aromatica. Arch. Microbiol. 170, 120131.
  • 64
    Leuthner, B. and Heider, J. (1998) A two-component system involved in regulation of anaerobic toluene metabolism in Thauera aromatica. FEMS Microbiol. Lett. 166, 3541.
  • 65
    Simoneit, B.R.T. and Lonsdale, P.F. (1982) Hydrothermal petroleum in mineralised mounds at the seabed of Guaymas Basin. Nature 295, 198202.
  • 66
    Hunkeler, D., Höhener, P. Häner, A., Bregnard, T. and Zeyer, J. (1995) Quantification of hydrocarbon mineralisation in a diesel fuel contaminated aquifer treated by in situ biorestoration. In: Ground Water Quality: Remediation and Protection (Kovar, K. and Krasny, J. Eds.), pp. 421–430. IAHS Press, Wallingford, UK.
  • 67
    Reinhard, M., Shnag, S., Kitanidis, P.K., Orwin, E., Hopkins, G.D. and LeBron, C.A. (1997) In situ BTEX biotransformation under intrinsic and enhanced nitrate- and sulfate-reducing conditions. Environ. Sci. Technol. 31, 2836.
  • 68
    Rabus, R. and Widdel, F. (1995) Conversion studies with substrate analogues of toluene in a sulfate-reducing bacterium, strain Tol2. Arch. Microbiol. 164, 448451.
  • 69
    Edwards, E.A. and Grbic-Galic, D. (1992) Complete mineralisation of benzene by aquifer microorganisms under strictly anaerobic conditions. Appl. Environ. Microbiol. 58, 26632666.
  • 70
    Zhang, X. and Young, L.Y. (1997) Carboxylation as an initial reaction in the anaerobic metabolism of naphthalene and phenanthrene by sulfidogenic consortia. Appl. Environ. Microbiol. 63, 47594764.
  • 71
    Zehnder, A.J.B. and Brock, T.D. (1980) Anaerobic methane oxidation: occurrence and ecology. Appl. Environ. Microbiol. 39, 194204.
  • 72
    Harder, J. (1997) Anaerobic methane oxidation by bacteria employing 14C-methane uncontaminated with 14C-carbon monoxide. Mar. Geol. 137, 1323.
  • 73
    Song, B., Young, L.Y. and Palleroni, N.J. (1998) Identification of denitrifier strain T1 as Thauera aromatica and proposal for emendation of the genus Thauera definition. Int. J. Syst. Bacteriol. 48, 889894.
  • 74
    Zhou, J., Fries, M.R., Chee-Sanford, J.C. and Tiedje, J.M. (1995) Phylogenetic analysis of a new group of denitrifiers capable of anaerobic growth on toluene and description of Azoarcus tolulyticus sp. nov. Int. J. Syst. Bacteriol. 45, 500506.
  • 75
    Hess, A., Zarda, B., Hahn, D., Häner, A., Stax, D., Höhener, P. and Zeyer, J. (1997) In situ analysis of denitrifying toluene- and m-xylene-degrading bacteria in a diesel fuel-contaminated laboratory aquifer column. Appl. Environ. Microbiol. 63, 21362141.