Diversity of alkane hydroxylase systems in the environment;Diversité des systèmes alcane hydroxylase dans l'environnement

Oil and Gas Science and Technology

Volumn 58, Issue 4, 2003, Pages 427-440

  van Beilen, J B ^a   Li, Z ^a   Duetz, W A ^a   Smits, T H M ^a,b   Witholt, B ^a  

^a ETH ZURICH   (Switzerland)

^b EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AQUIFERS; BACTERIA; BIODEGRADATION; BIOREMEDIATION; CATALYSIS; CHEMICAL ACTIVATION; CRUDE PETROLEUM; ENZYMES; HYDROGEN BONDS; OXIDATION; SOILS; YEAST;

COMETABOLIC DEGRADATION;

PARAFFINS;

ALKANE; BIOREMEDIATION; ENZYME; MICROORGANISM; OIL POLLUTION;

EID: 0041916075     PISSN: 12944475     EISSN: None     Source Type: Journal    
DOI: 10.2516/ogst:2003026     Document Type: Article

References (120)

1. Rosenberg, E., and Ron, E.Z. (1996) Bioremediation of Petroleum Contamination, in Bioremediation: Principles and Applications, Crawford, R.L., and Crawford, D.L. (Eds.) Cambridge University Press, Cambridge.
2. National Research Council (2002) Oil in the Sea III: Inputs, Fates, and Effects, National Academy Press, Washington DC.
3. Söhngen, N.L. (1906) Ueber Bakterien, welche Methan als Kohlenstoffnahrung und Energiequelle gebrauchen. Centralbl. Bakt. etc. Abt. II, 15, 513-517.
4. Söhngen, N.L. (1913) Benzin, Petroleum, Paraffinöl und Paraffin als Kohlenstoff- und Energiequelle für Mikroben. Zentr. Bacteriol. Parasitenk., Abt. II, 37, 595-609.
5. Brisbane, P.G., and Ladd, J.N. (1965) The Role of Microorganisms in Petroleum Exploration. Annu. Rev. Microbiol., 19.
6. Boulton, C.A., and Ratledge, C. (1984) The Physiology of Hydrocarbon-Utilizing Microorganisms. Top, Enzyme Ferment, Biotechnol., 9, 11-77.
7. Bühler, M., and Schindler, J. (1984) Aliphatic Hydrocarbons. In: Biotransformations, Kieslich, K. (Ed.), Verlag Chemie Weinheim, Weinheim.
8. Steffan, R.J., McClay, K., Vainberg, S., Condee, C.W., and Zhang, D. (1997) Biodegradation of the Gasoline Oxygenates Methyl Tert-Butyl Ether, Ethyl Tert-Butyl Ether, and Tert-Amyl Methyl Ether by Propane-Oxidizing Bacteria. Appl. Environ. Microbiol., 63, 4216-4222.
9. Chang, H.S., and Alvarez Cohen, L. (1995) Transformation Capacities of Chlorinated Organics by Mixed Cultures Enriched on Methane, Propane, Toluene, or Phenol. Biotechnol. Bioeng., 45, 440-449.
10. Britton, L.N. (1984) Microbial Degradation of Aliphatic Hydrocarbons. In: Microbial Degradation of Organic Compounds Gibson, D.T. (Ed.) Marcel Dekker, New York.
11. Hamamura, N., Storfa, R.T., Semprini, L., and Arp, D.J. (1999) Diversity in Butane Monooxygenases Among Butane-Grown Bacteria. Appl. Environ. Microbiol., 65, 4586-4593.
12. Murrell, J.C., Gilbert, B., and McDonald, I.R. (2000) Molecular Biology and Regulation of Methane Monooxygenase. Arch. Microbiol., 173, 325-332.
13. Labinger, J.A., and Bercaw, J.E. (2002) Understanding and Exploiting C-H Bond Activation. Nature, 417, 507-514.
14. Heider, J., Spormann, A.M., Beller, H.R., and Widdel, F. (1998) Anaerobic Bacterial Metabolism of Hydrocarbons. FEMS Microbiol. Rev., 22, 5, 459-473.
15. Hayaishi, O., Katagiri, M., and Rothberg, S. (1955) Mechanism of the Pyrocatechase Reaction. J. Am. Chem. Soc., 77, 5450-5451.
16. Witholt, B., de Smet, M.J., Kingma, J., van Beilen, J.B., Kok, M., Lageveen, R.G., and Eggink, G. (1990) Bioconversions of Aliphatic Compounds by Pseudomonas oleovorans in Multiphase Biorectors: Background and Economic Potential. Trends Biotechnol., 8, 46-52.
17. Li, Z., Feiten, H.J., Chang, D., Duetz, W.A., van Beilen, J.B., and Witholt, B. (2001) Preparation of (R)- and (S)-N-Protected-3-Hydroxypyrrolidines by Hydroxylation with Sphingomonas sp. HXN-200, a Highly Active, Regio-and Stereoselective, and Easy to Handle Biocatalyst. J. Org. Chem., 66, 8424-8430.
18. Watkinson, R.J., and Morgan, P. (1990) Physiology of Aliphatic Hydrocarbon-Degrading Micro-Organisms. Biodegradation, 1, 79-92.
19. Ashraf, W., Mihdhir, A., and Murrell, J.C. (1994) Bacterial Oxidation of Propane. FEMS Microbiol. Lett., 122, 1-6.
20. Sullivan, J.P., Dickinson, D., and Chase, H.A. (1998) Methanotrophs. Methylosinus trichosporium OB3b, sMMO, and their Application to Bioremediation. Crit. Rev. Microbiol., 24, 335-373.
21. Whyte, L.G., Hawari, J., Zhou, E., Bourbonnière, L., Inniss, W.E., and Greer, C.W. (1998) Biodegradation of Variable-Chain-Length Alkanes at Low Temperatures by a Psychrotrophic Rhodococcus sp. Appl. Environ. Microbiol., 64, 2578-2584.
22. Forney, F.W., and Markovetz, A.J. (1970) Subterminal Oxidation of Aliphatic Hydrocarbons. J. Bacteriol., 102, 281-282.
23. Forney, F.W., and Markovetz, A.J. (1968) Oxidative Degradation of Methyl Ketones II. Chemical Pathway for Degradation of 2-Tridecanone by Pseudomonas multivorans and Pseudomonas aeruginosa. J. Bacteriol., 96, 1055-1064.
24. Forney, F.W., Markovetz, A.J., and Kallio, R.E. (1967) Bacterial Oxidation of 2-Tridecanone to 1-Undecanol. J. Bacteriol., 93, 649-655.
25. Britton, L.N., and Markovetz, A.J. (1977) A Novel Ketone Monooxygenase from Pseudomonas cepacia. Purification and Properties. J. Biol. Chem., 252, 8561-8566.
26. Shum, A.C., and Markovetz, A.J. (1974) Purification and Properties of Undecyl Acetate Esterase from Pseudomonas cepacia Grown on 2-Tridecanone. J. Bacteriol., 118, 880-889.
27. Scheller, U., Zimmer. T., Becher, D., Schauer, F., and Schunck, W.H. (1998) Oxygenation Cascade in Conversion of n-Alkanes to α,ω-Dioic Acids Catalyzed by Cytochrome P450 52A3. J. Biol. Chem., 273, 32528-32534.
28. Broadway, N.M., Dickinson, F.M., and Ratledge, C. (1993) The Enzymology of Dicarboxylic Acid Formation by Corynebacterium sp. Strain 7E1C Grown on n-Alkanes. J. Gen. Microbiol., 139, 1337-1344.
29. Iida, T., Sumita, T., Ohta, A., and Takagi, M. (2000) The Cytochrome P450ALK Multigene Family of an n-Alkane-Assimilating Yeast, Yarrowia lipolytica: Cloning and Characterization of Genes Coding for New CYP52 Family Members. Yeast, 16, 1077-1087.
30. Maier, T., Foerster, H.H., Asperger, O., and Hahn, U. (2001) Molecular Characterization of the 56-kDa CYP153 from Acinetobacter sp. EB104. Biochem. Biophys. Res. Commun., 286, 652-658.
31. Cardini, G., and Jurtshuk, P. (1968) Cytochrome P-450 Involvement in the Oxidation of n-Octane by Cell-Free Extracts of Corynebacterium sp. Strain 7E1C. J. Biol. Chem., 243, 6070-6072.
32. Hamamura, N., Yeager, C. M., and Arp, D. J. (2001) Two Distinct Monooxygenases for Alkane Oxidation in Nocardioides sp. Strain CF8. Appl. Environ. Microbiol., 67, 4992-4998.
33. Sluis, M.K., Sayavedra Soto, L.A., and Arp, D.J. (2002) Molecular Analysis of the Soluble Butane Monooxygenase from "Pseudomonas butanovora". Microbiology, 148, 3617-3629.
34. Smits, T.H.M., Balada, S.B., Witholt, B., and van Beilen, J.B. (2002) Functional Analysis of Alkane Hydroxylases from Gram-Negative and Gram-Positive Bacteria. J. Bacteriol., 184, 1733-1742.
35. Maeng, J.H., Sakai, Y., Tani, Y., and Kato, N. (1996) Isolation and Characterization of a Novel Oxygenase that Catalyzes the First Step of n-Alkane Oxidation in Acinetobacter sp Strain M-1. J. Bacteriol., 178, 3695-3700.
36. Pandey, K.K., Mayilray, S., and Chakrabarti, T. (2002) Pseudomonas indica sp. Nov., a Novel Butane Utilizing Species. Int. J. Syst. Evol. Microbiol., 52, 1559-1567.
37. Padda, R S., Pandey, K.K., Kaul, S., Nair, V D., Jain, R.K., Basu, S.K., and Chakrabarti, T. (2001) A Novel Gene Encoding a 54 kDa Polypeptide is Essential for Butane Utilization by Pseudomonas sp. IMT37. Microbiology, 147, 2479-2491.
38. Babu, J.P., and Brown, L.R. (1984) New Type of Oxygenase Involved in the Metabolism of Propane and Isobutane. Appl. Environ. Microbiol., 48, 260-264.
39. Baptist, J.N., Gholson, R.K., and Coon, M.J. (1963) Hydrocarbon Oxidation by a Bacterial Enzyme System: I Products of Octane Oxidation. Biochim. Biophys. Acta, 69, 40-47.
40. van Beilen, J.B., Wubbolts, M.G., and Witholt, B. (1994) Genetics of Alkane Oxidation by Pseudomonas oleovorans. Biodegradation. 5, 161-174.
41. van Beilen, J.B., Panke, S., Lucchini, S., Franchini, A.G., Röthlisberger, M., and Witholt, B. (2001) Analysis of Pseudomonas putida Alkane Degradation Gene Clusters and Flanking Insertion Sequences: Evolution and Regulation of the Alk-Genes. Microbiology, 147, 1621-1630.
42. McKenna, E.J., and Coon, M.J. (1970) Enzymatic ω-Oxidation. IV. Purification and Properties of the ω-Hydroxylase of Pseudomonas Oleovorans. J. Biol. Chem., 245, 3882-3889.
43. Kok, M., Oldenhuis, R., van der Linden, M.P.G., Raatjes, P., Kingma, J., van Lelyveld, P.H., and Witholt, B. (1989) The Pseudomonas oleovorans Alkane Hydroxylase Gene. Sequence and Expression. J. Biol. Chem., 264, 5435-5441.
44. van Beilen, J.B., Penninga, D., and Witholt, B. (1992) Topology of the Membrane-Bound Alkane Hydroxylase of Pseudomonas oleovorans. J. Biol. Chem., 267, 9194-9201.
45. Peterson, J.A., and Coon, M J. (1968) Enzymatic ω-oxidation. III. Purification and Properties of Rubredoxin, a Component of the ω-Hydroxylation System of Pseudomonas oleovorans. J. Biol. Chem., 243, 329-334.
46. Kok, M., Oldenhuis, R., van der Linden, M.P.G., Meulenberg, C.H.C., Kingma, J., and Witholt, B. (1989) The Pseudomonas oleovorans AlkBAC Operon Encodes Two Structurally Related Rubredoxins and an Aldehyde Dehydrogenase. J. Biol. Chem., 264, 5442-5451.
47. van Beilen, J.B., Neuenschwander, M., Smits, T.H.M., Roth, C., Balada, S.B., and Witholt, B. (2002) Rubredoxins Involved in Alkane Oxidation. J. Bacteriol., 184, 1722-1732.
48. Ueda, T., and Coon, M.J. (1972) Enzymatic ω-Oxidation. VII. Reduced Diphosphopyridine Nucleotide-Rubredoxin Reductase: Properties and Function as an Electron Carrier in ω-Hydroxylation. J. Biol. Chem., 247, 5010-5016.
49. Eggink, G., Engel, H., Vriend, G., Terpstra, P., and Witholt, B. (1990) Rubredoxin Reductase of Pseudomonas oleovorans. Structural Relationship to Other Flavoprotein Oxidoreductases Based on One NAD and Two FAD Fingerprints. J. Mol. Biol., 212, 135-142.
50. Smits, T.H.M., Röthlisberger, M., Witholt, B., and van Beilen, J.B. (1999) Molecular Screening for Alkane Hydroxylase Genes in Gram-Negative and Gram-Positive Strains. Environ. Microbiol., 1, 307-318.
51. Shanklin, J., Whittle, E., and Fox, B.G. (1994) Eight Histidine Residues are Catalytically Essential in a Membrane-Associated Iron Enzyme, Stearoyl-CoA Desaturase, and are Conserved in Alkane Hydroxylase and Xylene Monooxygenase. Biochem., 33, 12787-12794.
52. Ratajczak, A., Geißdörfer, W., and Hillen, W. (1998) Alkane Hydroxylase from Acinetobacter sp. Strain ADP-I is Encoded by alkM and Belongs to a New Family of Bacterial Integral-Membrane Hydrocarbon Hydroxylases. Appl. Environ. Microbiol., 64, 1175-1179.
53. Marin, M.M., Smits, T.H.M., van Beilen, J.B., and Rojo, F. (2001) The Alkane Hydroxylase Gene of Burkholderia Cepacia RR10 is Under Catabolite Repression Control. J. Bacteriol., 183, 4202-4209.
54. Tani, A., Ishige, T., Sakai, Y., and Kato, N. (2001) Gene Structures and Regulation of the Alkane Hydroxylase Complex in Acinetobacter sp. Strain M-1. J. Bacteriol., 183, 1819-1823.
55. van Beilen, J.B., Kingma, J., and Witholt, B. (1994) Substrate Specificity of the Alkane Hydroxylase of Pseudomonas oleovorans GPol. Enzyme Microb. Technol., 16, 904-911.
56. Yadav, J.S., and Loper, J.C. (1999) Multiple P450alk (Cytochrome P450 Alkane Hydroxylase) Genes from the Halotolerant Yeast Debaryomyces Hansenii. Gene, 226, 139-146.
57. Ohkuma, M., Zimmer, T., Iida, T., Schunck, W.H., Ohta, A., and Takagi, M. (1998) Isozyme Function of n-Alkane-Inducible Cytochromes P450 in Candida Maltosa Revealed by Sequential Gene Disruption. J. Biol. Chem., 273, 3948-3953.
58. Schmitz, C., Goebel, I., Wagner, S., Vomberg, A., and Klinner, U. (2000) Competition Between n-Alkane-Assimilating Yeasts and Bacteria During Colonization of Sandy Soil Microcosms. Appl. Microbiol. Biotechnol., 54, 126-132.
59. Cardini, G., and Jurtshuk, P. (1970) The Enzymatic Hydroxylation of n-Octane by Corynebacterium sp. Strain 7E1C. J. Biol. Chem., 245, 2789-2796.
60. Müller, R., Asperger, O., and Kleber, H.P. (1989) Purification of Cytochrome P-450 from n-Hexadecane-Grown Acinetobacter Calcoaceticus. Biomed. Biochem. Acta., 48, 243-254.
61. Munro, A.W., and Lindsay, J.G. (1996) Bacterial Cytochromes P-450. Mol. Microbiol., 20, 1115-1125.
62. Jenkins, P.G., Raboin, D., and Moran, F. (1972) Mutants of Mycobacterium Rhodochrous with Modified Patterns of n-Paraffin Utilization. J. Gen. Microbiol., 72, 395-398.
63. Van der Linden, A.C., and Van Ravenswaay Claasen, J.C. (1971) Hydrophobic Enzymes in Hydrocarbon Degradation. Lipids, 6, 437-443.
64. Azoulay, E., Chouteau, J., and Davidovics, G. (1963) Isolement et Caractérisation des enzymes responsables de l'oxydation des hydrocarbures. Biochim. Biophys. Acta, 77, 554-567.
65. Vandecasteele, J.P., Blanchet, D., Tassin, J.P., Bonamy, A. M., and Guerrillot, L. (1983) Enzymology of Alkane Degradation in Pseudomonas aeruginosa. Acta Biotechnol., 3, 339-344.
66. Macham, L.P., and Heydeman, M.T. (1974) Pseudomonas aeruginosa Mutants Defective in Heptane Oxidation. J. Gen. Microbiol., 85, 77-84.
67. van Beilen, J.B., Veenhoff, L., and Witholt, B. (1998) Alkane Hydroxylase Systems in Pseudomonas aeruginosa Strains Able to Grow on n-Octane. In: New Frontiers in Screening for Microbial Biocatalysts Kieslich, K., van der Beek, C.P., de Bont, J.A.M., and van den Tweel, W.J.J. (Ed.), Elsevier Science B.V., Amsterdam.
68. Cole, S.T., Brosch, R., Parkhill, J., Garnier, T., Churcher C., Harris, D., Gordon, S.V., Eiglmeier, K., Gas, S., Barry, C.E., III. Tekaia, F., Badcock, K., Basham, D., Brown, D., Chillingworth, T., Connor, R., Davies, R., Devlin, K., Feltwell, T., Gentles, S., Hamlin, N., Holroyd, S., Hornsby, T., Jagels, K., Krogh, A., McLeah, J., Moule, S., Murphy, L., Oliver, K., Osborne, J., Quail, M.A., Rajandream, M.A., Rogers, J., Rutter, S., Soeger, K., Skelton, J., Squares, R., Squares, S., Sulston, J.E., Taylor, K., Whitehead, S., and Barrett, B.G. (1998) Deciphering the Biology of Mycobacterium tuberculosis from the Complete Genome Sequence. Nature, 393, 537-544.
69. Andreoni, V., Bernasconi, S., Colombo, M., van Beilen, J.B., and Cavalca, L. (2000) Detection of Genes for Alkane and Naphthalene Catabolism in Rhodococcus sp. Strain 1BN. Environ. Microbiol., 2, 572-577.
70. Juni, E., and Janik, A. (1969) Transformation of Acinetobacter calcoaceticus (Bacterium Anitratum). J. Bacteriol., 98, 281-288.
71. Asperger, O., and Kleber, H.P. (1991) Metabolism of Alkanes by Acinetobacter. In: The biology of Acinetobacter Towner, K. J. (Ed.), Plenum Press, New York.
72. Fewson, C.A. (1967) The Growth and Metabolic Versatility of the Gram-Negative Bacterium NCIB 8250 ('Vibrio 01'). J. Gen. Microbiol., 46, 255-266.
73. Yakimov, M.M., Golyshin, P.N., Lang, S., Moore, E.R.B., Abraham, W.R., Lünsdorf, H., and Timmis, K.N. (1998) Alcanivorax borkumensis Gen. Nov., sp. Nov., a New, Hydrocarbon-Degrading and Surfactant-Producing Marine Bacterium. Int. J. Syst. Bacteriol., 48, 339-348.
74. Palleroni, N.J., Kunisawa, R., Contopoulou, R., and Douderoff, M. (1973) Nucleic acid Homologies in the Genus Pseudomonas. Int. J. Syst. Bacteriol., 23, 333-339.
75. Golyshin, P.N., Chernikova, T., Abraham, W.R., Luensdorf, H., Timmis, K.N., and Yakimov, M.M. (2002) Oleiphilaceae Fam. Nov., to Include Oleiphilus messinensis Gen. Nov., sp. Nov., a Novel Marine Bacterium that Obligately Utilizes Hydrocarbons. Int. J. Syst. Evol. Microbiol., 52. 901-911.
76. Vomberg, A., and Klinner, U. (2000) Distribution of alkB Genes Within n-Alkane-Degrading Bacteria. J. Appl. Microbiol. 89, 339-348.
77. Panicker, G., and Bej, A.K. (2001) Detection of Biodegradative Genes Using Polymerase Chain Reaction in Antarctic Isolates. Genbank Entry AAK56792.
78. Schwartz, R.D., and McCoy, C.J. (1973) Pseudomonas oleovorans Hydroxylation-Epoxidation System: Additional Strain Improvements. Appl. Microbiol., 26, 217-218.
79. Stutz, E.W., Défago, G., and Kern, H. (1986) Naturally Occuring Fluorescent Pseudomonads Involved in Suppression of Black Root Rot of Tobacco. Phytopathology. 76, 181-185.
80. Holloway, B.W. (1969) Genetics of Pseudomonas. Bacteriol. Rev., 33, 419-443.
81. Guerra-Santos, L.H., Káppeli, O., and Fiechter, A. (1986) Dependence of Pseudomonas Aeruginosa Continuous Culture Biosurfactant Production on Nutritional and Environmental Factors. Appl. Microbiol. Biotechnol., 24, 443-448.
82. Thysse, G.J.E., and van der Linden, A.C. (1958) n-Alkane Oxidation by a Pseudomonas. Studies on the Intermediate Metabolism. Anton. Leeuwenhoek, 24, 298-308.
83. Fuhs, G.W. (1961) Der mikrobielle Abbau von Kohlen-wasserstoffen. Arch. Mikrobiol., 39, 374-422.
84. Lukins, H.B., and Foster, J.W. (1963) Utilization of Hydrocarbons and Hydrogen by Mycobacteria. Z. Allg. Mikrobiol., 3, 251-264.
85. Hou, C.T., Jackson, M.A., Bagby, M.O., and Becker, L.A. (1994) Microbial Oxidation of Cumene by Octane-Grown Cells. Appl. Microbiol. Biotechnol., 41. 178-182.
86. van Beilen, J.B.. Smits, T.H.M., Whyte, L.G., Schorcht, S., Röthlisberger, M., Plaggemeier, T., Engesser, K.H., and Witholt, B. (2002) Alkane Hydroxylases in Gram-Positive Strains. Environ. Microbiol., 4, 676-682
87. Schorcht, S. (1998) Mikrobiologische und Molekularbiologische Charakterisierung Alkanabbauender Bakteriengemeinschaften. PhD Thesis, Universität Bremen.
88. Plaggemeier, T. (2000) Elimination der Schwer Wasserlöslichen Modellabluftinhaltsstoffe n-Hexan und Toluol in Biorieselbettverfahren. PhD Thesis, Universität Stuttgart.
89. Whyte, L.G., Smits, T.H.M., Labbé, D., Witholt, B., Greer, C.W., and van Beilen, J.B. (2002) Cloning and Characterization of Multiple Alkane Hydroxylase Systems in Rhodococcus spp. Strains Q15 and 16531. Appl. Environ. Microbiol., 68, 5933-5942.
90. Higgins, D.G., and Sharp, P.M. (1988) CLUSTAL: a Package for Performing Multiple Sequence Alignment on a Microcomputer. Gene, 73, 237-244.
91. Smits, T.H.M., Seeger, M.A., Witholt, B., and van Beilen, J.B. (2001) New Alkane-Responsive Expression Vectors for E. coli and Pseudomonas. Plasmid, 46, 16-24.
92. Chakrabarty, A.M., Chou, G., and Gunsalus, I.C. (1973) Genetic Regulation of Octane Dissimulation Plasmid in Pseudomonas. Proc. Natl. Acad. Sci. USA, 70, 1137-1140.
93. Asperger, O., Wirkner, K., Schmidt, M., and Flechsig, E. (1994) Detection of Diverse Cytochrome P450-Dependent Biooxygenation Catalysts in Microorganisms Using a Multipurpose Inducer. Biocatalysis. 10, 233-246.
94. Morris, S.A., Radajewski, S., Willison, T.W., and Murrell, J.C. (2002) Identification of the Functionally Active Methanotroph Population in a Peat Soil Microcosm by Stable-Isotope Probing. Appl. Envipon. Microbiol., 68, 1446-1453.
95. Horz, H.P., Yimga, M.T., and Liesack, W. (2001) Detection of Methanotroph Diversity on Roots of Submerged Rice Plants by Molecular Retrieval of pmoA, mmoX, mxaF, and 16S rRNA and Ribosomal DNA, Including pmoA-Based Terminal Restriction Fragment Length Polymorphism Profiling. Appl. Environ. Microbiol., 67, 4177-4185.
96. Baker, P.W., Futamata, H., Harayama, S., and Watanabe, K. (2001) Molecular Diversity of pMMO and sMMO in a TCE-Contaminated Aquifer During Bioremediation. FEMS Microbiol. Ecol., 38, 161-167.
97. Sotsky, J.B., Greer, C.W., and Atlas, R.M. (1994) Frequency of Genes in Aromatic and Aliphatic Hydrocarbon Biodegradation Pathways Within Bacterial Populations from Alaskan Sediments. Can. J. Microbiol., 40, 981-985.
98. Knaebel, D.B., and Crawford, R.L. (1995) Extraction and Purification of Microbial DNA from Petroleum-Contaminated Soils and Detection of Low Numbers of Toluene, Octane and Pesticide Degraders by Multiplex Polymerase Chain Reaction and Southern Analysis. Mol. Ecol., 4, 579-591.
99. Whyte, L.G., Greer, C.W., and Inniss, W.E. (1996) Assessment of the Biodegradation Potential of Psychrotrophic Microorganisms. Can. J. Microbiol., 42, 99-106.
100. Guo, C., Sun, W., Harsh, J.B., and Ogram, A. (1997) Hybridisation Analysis of Microbial DNA from Fuel Oil-Contaminated and Noncontaminated Soil. Microb. Ecol., 34, 178-187.
101. Stapleton, R.D., and Sayler, G.S. (1998) Assessment of the Microbiological Potential for the Natural Attenuation of Petroleum Hydrocarbons in a Shallow Aquifer System. Microb. Ecol., 36, 349-361.
102. Stapleton, R.D.. Sayler, G.S., Boggs, J. M., Libelo, E.L., Stauffer, T., and MacIntyre, W.G. (2000) Changes in Subsurface Catabolic Gene Frequencies During Natural Attenuation of Petroleum Hydrocarbons. Environ. Sci. Technol., 34, 1991-1999.
103. Siciliano, S.D., Fortin, N., Mihoc, A., Wisse, G., Labelle, S., Beaumier, D., Ouellette, D., Roy, R., Whyte, L.G., Banks, M.K., Schwab, P., Lee, K., and Greer, C.W. (2001) Selection of Specific Endophytic Bacterial Genotypes by Plants in Response to Soil Contamination. Appl. Environ. Microbiol., 67, 2469-2475.
104. Whyte, L.G., Schultz, A., van Beilen, J.B., Luz, A.P., Pellizari, D., Labbé, D., and Greer, C.W. (2002) Prevalence of Alkane Monooxygenase Genes in Arctic Hydrocarbon-Contaminated and Pristine Soils. FEMS Microbiol. Ecol., 41, 141-150.
105. Whyte, L.G., Schultz, A., van Beilen, J.B., Luz, A.P., Pellizari, D., Labbé, D., and Greer, C.W. (2002) Prevalence of Alkane Monooxygenase Genes in Arctic and Antarctic Hydrocarbon-Contaminated and Pristine Soils. FEMS Microbiol. Ecol., 41, 141-150.
106. Abbott, B.J., and Hou, C.T. (1973) Oxidation of 1-Alkenes to 1,2-Epoxyalkanes by Pseudomonas oleovorans. Appl Microbiol, 26, 86-91.
107. Van Ravenswaay Claasen, J.C., and Van der Linden, A C. (1971) Substrate Specificity of the Paraffin Hydroxylase of Pseudomonas aeruginosa. Ant. Leeuwenhoek, 37, 339-352.
108. Kiener, A. (1992) Enzymatic Oxidation of Methyl Groups on A romatic Heterocycles: a Versatile Method for the Preparation of Heteroaromatic Carboxylic Acids. Angew. Chem. Int. Ed. Engl., 31, 774-775.
109. Johnstone, S.L., Phillips, G.T., Robertson, B.W., Watts, P.D., Bertola, M.A., Koger, H.S., and Marx, A.F. (1986) Stereoselective Synthesis of S-(-)-ß-blockers via Microbially Produced Epoxide Intermediates. In: Biocatalysis in Organic Media Laane, C., Tramper, J., and Lilly, M.D. (Ed.), Elsevier. Amsterdam,
110. Li, Z., Feiten, H.J., van Beilen, J.B., Duetz, W., and Witholt, B. (1999) Preparation of Optically Active N-benzyl-3-Hydroxypyrrolidine by Enzymatic Hydroxylation. Tetrahedron: Asymmetry, 10, 1323-1333.
111. Fu, H., Newcomb. M., and Wong, C.H. (1991) Pseudomonas oleovorans Monooxygenase Catalyzed Asymmetric Epoxidation of Allyl Alcohol Derivatives and Hydroxylation of a Hypersensitive Radical Probe with the Radical Ring Opening State Exceeding the Oxygen Rebound State. J. Am. Chem. Soc., 113, 5878-5880.
112. Chang, D., Witholt, B., and Li, Z. (2000) Preparation of (S)-N-Substituted 4-Hydroxy-Pyrrolidine-2-Ones by Regio- and Stereoselective Hydroxylation with Sphingomonas sp. HXN-200. Org. Lett., 2, 3949-3952.
113. Chang, D., Feiten, H.J., Engesser, K.H., van Beilen, J.B., Witholt, B., and Li, Z. (2002) Practical Syntheses of N-Substituted 3-Hydroxyazetidines and 4-Hydroxypiperidines by Hydroxylation with Sphingomonas sp. HXN-200. Org. Lett., 4, 1859-1862.
114. Clifford, K.H., Phillips, G.T., and Marx, A.F. (1988) Process for the Preparation of Substituted Phenoxy Propanoic Acids. US Patent 5 037 .759.
115. Matsui, T., and Furuhashi, K. (1995) Asymmetric Oxidation of Isopropylmoieties of Aliphatic and Aromatic Hydrocarbons by Rhodococcus sp. 11B. Biosci, Biotech. Biochem., 59, 1342-1344.
116. Wilcox, D.W., Autenrieth, R.L., and Bonner, J.S. (1995) Propane-Induced Biodegradation of Vapor Phase Trichloroethylene. Biotechnol. Bioeng., 46, 333-342.
117. Dupasquier, D., Revah, S., and Auria, R. (2002) Biofiltration of Methyl Yert-Butyl Ether Vapors by Cometabolism with Pentane: Modeling and Experimental Approach. Environ. Science Technol., 36, 247-253.
118. Liu, C.Y., Speitel, G.E.J., and Georgiou, G. (2001) Kinetics of Methyl Tertiary-Butyl Ether Cometabolism at Low Concentrations by Pure Cultures of Butane-Degrading Bacteria. Appl. Environ. Microbiol., 67, 2197-2201.
119. Garnier, P.M., Auria, R., Augur, C., and Revah, S. (2000) Cometabolic Biodegradation of Methyl Tertiary-Butyl Ether by a Soil Consortium: Effect of Components Present in Gasoline. J. Gen. Appl. Microbiol., 46, 79-84.
120. Garnier, P.M., Auria, R., Augur. C., and Revah, S. (1999) Cometabolic Biodegradation of Methyl Tertiary-Butyl Ether by Pseudomonas aeruginosa Grown on Pentane. Appl. Microbiol. Biotechnol., 51, 498-503.