Controlling regiospecific oxidation of aromatics and the degradation of chlorinated aliphatics via active site engineering of toluene monooxygenases

Pseudomonas

Volumn 4, Issue , 2006, Pages 237-286

  Fishman, Ayelet ^a   Tao, Ying ^a   Vardar, Gönül ^a   Rui, Lingyun ^a   Wood, Thomas K ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 64449086530     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/0-387-28881-3_8     Document Type: Chapter

References (135)

1. Azerad, R., 2001, Chemical biotechnology better enzyme for green chemistry. Curr. Opin. Biotechnol., 12:533-534.
2. Bainbridge, G., Anralojc, P.J., Madgwick, P.J., Pitts, J.E., and Parry, M.A.J., 1998, Effect of mutation of lysine-128 of the large subunit of ribulose bisphosphate carboxylase/oxygenase from Anacystis nidulans. Biochem. J., 336:387-393.
3. Bertoni, G., Bolognese, F., Galli, E., and Barbieri, P., 1996, Cloning of the genes for and characterization of the early stages of toluene and o-xylene catabolism in Pseudomonas stutzeri OX1. Appl. Environ. Microbiol., 62:3704-3711.
4. Bhushan, B., Samanta, S.K., and Jain, R.K., 2000, Indigo production by naphthalenedegrading bacteria. Lett. Appl. Microbiol., 31:5-9.
5. Bradley, P.M., and Chapelle, F.H., 1998, Effect of contaminant concentration on aerobic microbial mineralization of DCE and VC in stream-bed sediments. Environ. Sci. Technol., 32:553-557.
6. Branden, C., andTooze, J., 1999, Introduction to Protein Structure, 2nd ed. Garland Publishing Inc., New York, USA.
7. Buhler, B., Witholt, B., Hauer, B., and Schmid, A., 2002, Characterization and application of xylene monooxygenase for multistep biocatalysis. Appl. Environ. Microbiol., 68:560- 568.
8. Bui, V.P., Hansen, T.V., Stenstrom, Y., and Hudlicky, T., 2000, Direct biocatalytic synthesis of functionalized catechols: A green alternative to traditional methods with high effective mass yield. Green Chem., 2:263-265.
9. Buolamwini, J.K., 2000, Cell cycle molecular targets in novel anticancer drug discovery. Curr. Pharm. Des., 6:379-392.
10. Burton, S.G., 2003, Oxidizing enzymes as biocatalysts. Trends Biotechnol., 21:543-549.
11. Bylina, E.J., Coleman, W.J., Dilworth, M.R., Robles, S.J., Tanner, M.A., Yang, M.M., and Youvan, D.C., 2000, Solid-phase enzyme screening. ASM News, 66:211-217.
12. Byrne, AM., Kukor, J.J., and Olsen, R.H., 1995, Sequence analysis of the gene cluster encoding toluene-3-monooxygenase from Pseudomonas pickettii PKO1. Gene, 154:65-70.
13. Byrne, A.M., and Olsen, R.H., 1996, Cascade regulation of the toluene-3-monooxygenase operon (tbuA1UBVA2C) of Burkholderia pickettii PKO1: role of the tbuA1 promoter (PtbuA1) in the expression of its cognate activator, TbuT. J. Bacteriol., 178:6327-6337.
14. Cafaro, V., Izzo, V., Scognamiglio, R., Notomista, E., Capasso, P., Casbarra, A., Pucci, P., and Di Donato, A., 2004, Phenol hydroxylase and toluene/o-xylene monooxygenase from Pseudomonas stutzeri OX1: interplay between two enzymes. Appl. Environ. Microbiol., 70:2211- 2219.
15. Canada, K.A., Iwashita, S., Shim, H., and Wood, T.K., 2002, Directed evolution of toluene ortho-monooxygenase for enhanced 1-naphthol synthesis and chlorinated ethene degradation. J. Bacteriol., 184:344-349.
16. Carter, S.R., and Jewell, W.J., 1993, Biotransformation of tetrachloroethylene by anaerobic attached-films at low temperatures. Water Res., 27:607-615.
17. Casellas, M., Grifoll, M., Bayona, J.M., and Solanas, A.M., 1997, New metabolites in the degradation of fluorene by Arthrobacter sp. strain F101. Appl. Environ. Microbiol. 63:819- 826.
18. Cheng, L. Feb 16 1999, Forthcoming production reduction of 2-naphthol for environmental protection. China Chem. Rep. Accessed from High Beam Research, Inc., July 15 2004 www.highbeam.com.
19. Dolfing, J., van den Wijngaard, A.J., and Janssen, D.B., 1993, Microbiological aspects of the removal of chlorinated hydrocarbons from air. Biodegradation, 4:261-282.
20. Draths, K.M., and Frost, J.W., 1991, Conversion of D-glucose into catechol: The not-socommon pathway of aromatic biosynthesis. J. Am. Chem. Soc. 113:9361-9363.
21. Draths, K.M., and Frost, J.W., 1995, Environmentally compatible synthesis of catechol from D-glucose. J. Am. Chem. Soc. 117:2395-2400.
22. Dressler, H. 1994, Resorcinol, Its Uses and Derivatives, 1st ed. Plenum Press, New York.
23. Egli, C., Scholtz, R., Cook, A.M., and Leisinger, T., 1987, Anaerobic dechlorination of tetrachloromethane and 1, 2-dichloroethane to degradable products by pure cultures of Desulfobacterium sp. and Methanobacterium sp. FEMS Microbiol. Lett., 43:257-261.
24. Elango, N., Radhakrishnan, R., Froland, W.A., Wallar, B.J., Earhart, C.A., Lipscomb, J.D., and Ohlendorf, D.H., 1997, Crystal structure of the hydroxylase component of methane monooxygenase from Methylosinus trichosporium OB3b. Protein. Sci., 6:556-568.
25. Ensley, B.D., 1991, Biochemical diversity of trichloroethylene metabolism. Annu. Rev. Microbiol., 45:283-299.
26. Ensley, B.D., Ratzkin, B.J., Osslund, T.D., Simon, M.J., Wackett, L.P., and Gibson, D.T., 1983, Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo. Science, 222:167-169.
27. Fishman, A., Tao, Y., Bentley, W., and Wood., T.K., 2004, Protein engineering of toluene 4-monooxygenase of Pseudomonas mendocina KR1 for synthesizing 4-nitrocatechol from nitrobenzene. Biotechnol. Bioeng., 87:779-790.
28. Fishman, A., Tao, Y., Rui, L., and Wood, T.K., 2005, Controlling the regiospecific oxidation of aromatics via active site engineering of toluene para-monooxygenase of Ralstonia pickettii PKO1. J. Biol. Chem., 290:506-514.
29. Fishman, A., Tao, Y., and Wood, T.K., 2004, Physiological relevance of successive hydroxylations of toluene by toluene para-monooxygenase of Ralstonia pickettii PKO1. Biocatalysis Biotransformation, 22:283-289.
30. Fishman, A., Tao, Y., and Wood, T.K., 2004, Toluene 3-monooxygenase of Ralstonia pickettii PKO1 is a para-hydroxylating enzyme. J. Bacteriol., 186:3117-3123.
31. Fox, B.G., Borneman, J.G., Wackett, L.P., and Lipscomb, J.D., 1990, Haloalkene oxidation by the soluble methane monooxygenase from Methylosinus trichosporium OB3b: mechanistic and environmental implications. Biochem., 29:6419-6427.
32. Frost, J.W., and Lievense, J., 1994, Prospects for biocatalytic synthesis of aromatics in the 21st century. New J. Chem., 18:341-348.
33. Gillam, E.M.J., Notley, L.M., Cai, H., De Voss, J.J., and Guengerich, F.P., 2000, Oxidation of indole by cytochrome P450 enzymes. Biochem., 39:13817-13824.
34. Gillner, M., Moore, G.S., Cederberg, H., and Gustafsson, K., 1994, Hydroquinone, environmental health criteria 157. International Programme on Chemical Safety.
35. Guex, N., and Peitsch, M.C., 1997, SWISS-MODEL and the Swiss-PdbViewer: An environment for comparative protein modelling. Electrophoresis, 18:2714-2723.
36. Hamel, P., and Girard, Y., 1994, Synthesis of Dephostatin, a novel protein tyrosine phosphatase inhibitor. Tetrahedron Lett., 35:8101-8102.
37. Hartog, J., and Wouters, W., 1988, Flesinoxan hydrochloride. Drugs future 1:31-33.
38. Held, M., Suske, W., Schmid, A., Engesser, K.-H., Kohler, H.-P.E., Witholt, B., andWubbolts, M.G., 1998, Preparative scale production of 3-substituted catechols using a novel monooxygenase from Pseudomonas azelaica HBP1. J. Mol. Catalysis B: Enzymatic, 5:87-93.
39. Hisaindee, S., and Clive, D.L.J., 2001, A synthesis of puraquinonic acid. Tetrahedron Lett., 42:2253-2255.
40. Hoessel, R., Leclerc, S., Endicott, J.A., Noble, M.E.M., Lawrie, A., Tunnah, P., Leost, M., Damiens, E., Marie, D., Marko, D., Niederberger, E., Tang, W., Eisenbrand, G., and Meijer, L., 1999, Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases. Nat. Cell Biol., 1:60-67.
41. M. Howe-Grant (ed.), 1991, Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed, Vol. 13. Wiley-Interscience Publishers, New York.
42. Hua, D.H., Tamura, M., Huang, X., Stephany, H.A., Helfrich, B.A., Perchellet, E.M., Sperfslage, B.J., Perchellet, J.-P., Jiang, S., Kyle, D.E., and Chiang, P.K., 2002, Syntheses and bioactivities of substituted 9, 10-dihydro-9, 10-[1, 2] benzenoanthracene-1, 4, 5, 8-tetrones. Unusual reactivities with amines. J. Org. Chem., 67:2907-2912.
43. Jahng, D., Kim, C.S., Hanson, R.S., and Wood, T.K., 1996, Optimization of trichloroethylene degradation using soluble methane monooxygenase of Methylosinus trichosporium OB3b expressed in recombinant bacteria. Biotechnol. Bioeng., 51:349-359.
44. Jahng, D., and Wood, T.K., 1994, Trichloroethylene and chloroform degradation by a recombinant pseudomonad expressing soluble methane monooxygenase from Methylosinus trichosporium OB3b. Appl. Environ. Microbiol., 60:2473-2482.
45. Johnson, G.R., and Olsen, R.H., 1997, Multiple pathways for toluene degradation in Burkholderia sp. strain JS150. Appl. Environ. Microbiol., 63:4047-4052.
46. Kadiyala, V., and Spain, J.C., 1998, A two-component monooxygenase catalyzes both the hydroxylation of p-nitrophenol and the oxidative release of nitrite from 4-nitrocatechol in Bacillus sphaericus JS905. Appl. Environ. Microbiol., 64:2479-2484.
47. Keenan, B., Leungsakul, T., Smets, B., and Wood, T.K., 2004, Saturation mutagenesis of Burkholderia cepacia R34 2, 4-DNT dioxygenase at DntAc Valine 350 for synthesizing nitrohydroquinone, methylhydroquinone, and methoxyhydroquinone. Appl. Environ. Microbiol., 70:3222-3231.
48. Kirk, O., Borchert, T.V., and Fuglsang, C.C., 2002, Industrial enzyme applications. Curr. Opin. Biotechnol., 13:345-351.
49. Krolikowska, A., Bokszczanin, W., Kozlowski, A., and Dzikowicz, T., April 1991, Mixtures of dihydroxybenzene derivatives and alkylphenols as rust inhibitors for paints. Polland patent 153, 464.
50. Kukor, J.J., and Olsen, R.H., 1992, Complete nucleotide sequence of tbuD, the gene encoding phenol/cresol hydroxylase from Pseudomonas pickettii PKO1, and functional analysis of the encoded enzyme. J. Bacteriol., 174:6518-6526.
51. Laufer, W., Niederer, J.P.M., and Hoelderich, W.F., 2002, Newdirect hydroxylation of benzene with oxygen in the presence of hydrogen over bifunctional palladium/platinum catalysts. Adv. Synth. Catalysis, 344:1084-1089.
52. Leahy, J.G., Batchelor, P.J., and Morcomb, S.M., 2003, Evolution of the soluble diiron monooxygenases. FEMS Microbiol. Rev., 27:449-479.
53. Leahy, J.G., Byrne, A.M., and Olsen, R.H., 1996, Comparison of factors influencing trichloroethylene degradation by toluene-oxidizing bacteria. Appl. Environ. Microbiol., 62:825-833.
54. Leahy, J.G., Johnson, G.R., and Olsen, R.H., 1997, Cross-regulation of toluene monooxygenases by the transcriptional activators TbmR and TbuT. Appl. Environ. Microbiol., 63:3736- 3739.
55. Learmonth, D.A., and Freitas, A.P., 2002, Chemical synthesis and characterization of conjugates of a novel catechol-o-methyltransferase inhibitor. Bioconj. Chem., 13:1112-1118.
56. Learmonth, D.A., Vieira-Coelho, M.A., Benes, J., Alves, P.C., Borges, N., Freitas, A.P., and Soares-da-Silva, P., 2002, Synthesis of 1-(3, 4-dihydroxy-5-nitrophenyl)-2-phenyl-ethanone and derivatives as potent and long acting peripheral inhibitors of catechol-o-methyltransferase. J. Med. Chem., 45:685-695.
57. Leung, S.W., Watts, R.J., and Miller, G.C., 1992, Degradation of perchloroethylene by Fenton's reagent: Speciation and pathway. J. Environ. Qual., 21:377-381.
58. Li, Z., van Beilen, J.B., Duetz, W.A., Schmid, A., de Raadt, A., Grienge, H., and Witholt, B., 2002, Oxidative biotransformations using oxygenases. Curr. Opin. Chem. Biol., 6:136- 144.
59. Liptakova, B., Bahidsky, M., and Hronec, M., 2004, Preparation of phenol from benzene by one-step reaction. Appl. Catalysis A: Gen. 263:33-38.
60. Low, D.W., and Hill, M.G., 2000, Backbone-engineered high-potential iron proteins: effects of active-site hydrogen bonding on reduction potential. J. Am. Chem. Soc., 122:11039- 11040.
61. Luu, P.P., Yung, C.W., Sun, A.K.-Y., and Wood, T.K., 1995, Monitoring trichloroethylene mineralization by Pseudomonas cepacia G4 PR1. Appl. Microbiol. Biotechnol., 44:259-264.
62. Macias, F.A., Marin, D., Chinchilla, D., and Molinillo, J.M.G., 2002, First total synthesis of (+/-)-helibisabonol A. Tetrahedron Lett. 43:6417-6420.
63. Masumoto, Y., Hamada, R., Yokota, K., Nishiyama, S., and Tsuruya, S., 2002, Liquid-phase oxidation of benzene to phenol by vanadium catalysts in aqueous solvent with high acetic acid concentration. J. Mol. Catalysis A: Chem., 184:215-222.
64. Maugard, T., Enaud, E., de La Sayette, A., Choisy, P., and Legoy, M.D., 2002, Beta-glucosidasecatalyzed hydrolysis of indican from leaves of Polygonum tinctorium. Biotechnol. Prog., 18:1104-1108.
65. Maymo-Gatell, X., Chien, Y.-T., Gossett, J.M., and Zinder, S.H., 1997, Isolation of a bacterium that reductively dechlorinates tetrachloroethene to ethene. Science, 276:1568-1571.
66. McCarty, P.L., 1997, Breathing with chlorinated solvents. Science, 276:1521-1522.
67. McClay, K., Fox, B.G., and Steffan, R.J., 1996, Chloroform mineralization by tolueneoxidizing bacteria. Appl. Environ. Microbiol., 62:2716-2722.
68. McMurry, J., 2004, Organic Chemistry, 6th ed. Thomson Learning Inc., Belmont, CA, USA.
69. Meloni, D., Monaci, R., Rombi, E., Guimon, C., Martinez, H., Fechete, I., and Dumitriu, E., 2002, Synthesis and characterization of MCM-22 zeolites for the N2O oxidation of benzene to phenol. Stud. Surface Sci. Catalysis, 142A:167-174.
70. Meng, M., Lee, C., Bagdasarian, M., and Zeikus, J.G., 1991, Switching substrate preference of the thermophilic xylose isomerase from D-xylose to D-glucose by redesigning the substrate binding pocket. Proc. Natl. Acad. Sci. USA, 88:4015-4019.
71. Meyer, A., Schmid, A., Held, M., Westphal, A.H., Rothlisberger, M., Kohler, H.-P.E., van Berkel, W. J. H., and Witholt, B., 2002, Changing the substrate reactivity of 2-hydroxybiphenyl 3-monooxygenase from Pseudomonas azelaica HBP1 by directed evolution. J. Biol. Chem. 277:5575-5582.
72. Mitchell, K.H., 2002, Mutagenesis studies revealing the complementary roles of effector protein binding and the hydroxylase active site catalysis by toluene 4-monooxygenase. Ph.D. thesis. University of Wisconsin, Madison.
73. Mitchell, K.H., Studts, J.M., and Fox, B.G., 2002, Combined participation of hydroxylase active site residues and effector protein binding in a para to ortho modulation of toluene-4- monooxygenase regiospecificity. Biochem., 41:3176-3188.
74. Murdock, D., Ensley, B.D., Serdar, C., and Thalen, M., 1993, Construction of metabolic operons catalyzing the de novo biosynthesis of indigo in Escherichia coli. Bio/Technol., 11:381- 386.
75. Nelson, M.J.K., Montgomery, S.O., Mahaffey, W.R., and Pritchard, P.H., 1987, Biodegradation of trichloroethylene and involvement of an aromatic biodegradative pathway. Appl. Environ. Microbiol., 53:949-954.
76. Nelson, M.J.K., Montgomery, S.O., O'Neill, E.J., and Pritchard, P.H., 1986, Aerobic metabolism of trichloroethylene by a bacterial isolate. Appl. Environ. Microbiol., 52:383- 384.
77. Newman, L.M., and Wackett, L.P., 1995, Purification and characterization of toluene 2- monooxygenase from Burkholderia cepacia G4. Biochem., 34:14066-14076.
78. Niwa, S., Eswaramoorthy, M., Nair, J., Raj, A., Itoh, N., Shoji, H., Namba, T., and Mizukami, F., 2002, A one-step conversion of benzene to phenol with a palladium membrane. Science, 295:105-107.
79. Notomista, E., Lahm, A., Di Donato, A., and Tramontano, A., 2003, Evolution of bacterial and archaeal multicomponent monooxygenases. J. Mol. Evol., 56:435-445.
80. O'Connor, K.E., and Hartmans, S., 1998, Indigo formation by aromatic hydrocarbondegrading bacteria. Biotechnol. Lett., 20:219-223.
81. O'Connor, K.E., Dobson, A.D., and Hartmans, S., 1997, Indigo formation by microorganisms expressing styrene monooxygenase activity. Appl. Environ. Microbiol., 63:4287-4291.
82. Olah, G.A., Keumi, T., Lecoq, J.C., Fung, A.P., and Olah, J.A., 1991, Oxyfunctionalization of hydrocarbons. Acid-dependent high regioselectivity hydroxylation of naphthalene with hydrogen peroxide giving 1- or 2-naphthol. J. Org. Chem. 56:6148-6151.
83. Olsen, R.H., Kukor, J.J., and Kaphammer, B., 1994, A novel toluene-3-monooxygenase pathway cloned from Pseudomonas pickettii PKO1. J. Bacteriol., 176:3749-3756.
84. Othmer, K. 1991, Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed, Vol. 13.Wiley- Interscience Publishers, New York.
85. Palumbo, A., Napolitano, A., and d'Ischia, M., 2002, Nitrocatechols versus nitrocatecholamines as novel competitive inhibitors of neuronal nitric oxide synthase: lack of the aminoethyl side chain determines loss of tetrahydrobiopterin-antagonizing properties. Bioorg. Med. Chem. Lett., 12:13-16.
86. Park, J., Kukor, J.J., and Abriola, L.M., 2002, Characterization of the adaptive response to trichloroethylene-mediated stresses in Ralstonia pickettii PKO1. Appl. Environ. Microbiol., 68:5231-5240.
87. Peitsch, M.C., 1995, Protein modeling by e-mail. Bio/Technol. 13:658-660.
88. Peng, J., Shi, F., Gu, Y., and Deng, Y., 2003, Highly selective and green aqueous-ionic liquid biphasic hydroxylation of benzene to phenol with hydrogen peroxide. Green Chem., 5:224- 226.
89. Perry, R.H., and Chilton, C.H., 1973, Chemical Engineers' Handbook, 5th ed. McGraw-Hill Inc., New York, USA.
90. Pikus, J.D., Mitchell, K.H., Studts, J.M., McClay, K., Steffan, R.J., and Fox, B.G., 2000, Threonine 201 in the diiron enzyme toluene-4-monooxygenase is not required for catalysis. Biochem., 39:791-799.
91. Pikus, J.D., Studts, J.M., McClay, K., Steffan, R.J., and Fox, B.G., 1997, Changes in the regiospecificity of aromatic hydroxylation produced by active site engineering in the diiron enzyme toluene 4-monooxygenase. Biochem., 36:9283-9289.
92. Resnick, S.M., Lee, K., and Gibson, D.T., 1996, Diverse reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816. J. Ind. Microbiol., 17:438- 457.
93. Robinson, G.K., Stephens, G.M., Dalton, H., and Geary, P.J., 1992, The production of catechols from benzene and toluene by Pseudomonas putida in glucose fed-batch culture. Biocatalysis, 6:81-100.
94. Rosenzweig, A.C., Brandstetter, H., Whittington, D.A., Nordlund, P., Lippard, S.J., and Frederick, C.A., 1997, Crystal structures of the methane monooxygenase hydroxylase from Methylococcus capsulatus (bath): implications for substrate gating and component interactions. Proteins Struct. Funct. Genet., 29:141-152.
95. Rosenzweig, A.C., Nordlund, P., Takahara, P.M., Frederick, C.A., and Lippard, S.J., 1995, Geometry of the soluble methane monooxygenase catalytic diiron center in two oxidation states. Chem. Biol., 2:409-418.
96. Ross, S., 1997, A First Course in Probability, p. 252. Prentice Hall. Englewood Cliffs, NJ.
97. Rui, L., Cao, L., Chen, W., Reardon, K.F., and Wood, T.K., 2004, Active site engineering of the epoxide hydrolase from Agrobacterium radiobacter AD1 to enhance aerobic mineralization of cis-1, 2-dichloroethylene in cells expressing an evolved toluene ortho-monooxygenase. J. Biol. Chem., 279:46810-46817.
98. Rui, L., Kwon, Y.-M., Fishman, A., Reardon, K.F., andWood, T.K., 2004, Saturation mutagenesis of toluene ortho-monooxygenase of Burkholderia cepacia G4 for enhanced 1-naphthol synthesis and chloroform degradation. Appl. Environ. Microbiol., 70:3246-3252.
99. Rui, L., Kwon, Y.-M., Reardon, K.F., and Wood, T.K., 2004, Metabolic pathway engineering to enhance aerobic degradation of chlorinated ethenes and to reduce their toxicity by cloning a novel glutathione S-transferase an evolved toluene ortho-monooxygenase, and gammaglutamylcysteine synthetase. Environ. Microbiol., 6:491-500.
100. Rui, L., Reardon, K.F., and Wood, T.K., 2005, Altering toluene ortho-monooxygenase of Burkholderia cepacia G4 for regiospecific hydroxylation of indole to form indigoid compounds. Appl. Microbiol. Biotechnol., 66:422-429.
101. Ryoo, D., Shim, H., Canada, K., Barbieri, P., and Wood, T.K., 2000, Aerobic degradation of tetrachloroethylene by toluene-o-xylene monooxygenase of pseudomonas stutzeri OX1. Nat. Biotechnol., 18:775-778.
102. Sakamoto, T., Joern, J.M., Arisawa, A., and Arnold, F.H., 2001, Laboratory evolution of toluene dioxygenase to accept 4-picoline as a substrate. Appl. Environ. Microbiol., 67:3882- 3887.
103. Sazinsky, M.H., Bard, J., Di Donato, A., and Lippard, S.J., 2004, Crystal structure of the toluene/o-xylene monooxygease hydroxylase from Pseudomonas stutzeri OX1. J. Biol. Chem., 279:30600-30610.
104. Scharrenburg, G.J.M., and Frankena, J., 1996, Biokatalyse helpt farmaceutische industrie bij asymmetrische synthese. Chemisck Weekblad, 284-286.
105. Schmid, A., Dordick, J.S., Hauer, B., Kiener, A., Wubbolts, M., and Witholt, B., 2001, Industrial biocatalysis today and tomorrow. Nature, 409:258-268.
106. Schoemaker, H. E., Mink, D., and Wubbolts, M.G., 2003, Dispelling the myths - biocatalysis in industrial synthesis. Science 299:1694-1697.
107. Schwede, T., Kopp, J., Guex, N., and Peitsch, M.C., 2003, SWISS-MODEL: An Automated Protein Homology-Modeling Server. Nucleic Acids Research 31:3381-3385.
108. Sharma, P.K., and McCarty, P.L., 1996, Isolation and characterization of a facultatively aerobic bacterium that reductively dehalogenates tetrachloroethene to cis-1, 2-dichloroethene. Appl. Environ. Microbiol., 62:761-765.
109. Sheilds, M.S., Reagin, M.J., Gerger, R.R., Campbell, R., and Somerville, C., 1995, TOM, a new aromatic degradative plasmid from Burkholderia cepacia G4. Appl. Environ. Microbiol., 61:1352-1356.
110. Shields, M.S., Montgomery, S.O., Chapman, P.J., Cuskey, S.M., and Pritchard, P.H., 1989, Novel pathway of toluene catabolism in the trichloroethylene-degrading bacterium G4. Appl. Environ. Microbiol., 55:1624-1629.
111. Shim, H., and Wood, T.K., 2000, Aerobic degradation of mixtures of chlorinated aliphatics by cloned toluene-o-xylene monooxygenase and toluene o-monooxygenase in resting cells. Biotechnol. Bioeng., 70:693-698.
112. Spain, J.C., and Gibson, D.T., 1988, Oxidation of substituted phenols by Pseudomonas putida F1 and Pseudomonas sp. strain JS6. Appl. Environ. Microbiol., 54:1399-1404.
113. Steffan, R.J., and McClay, K.R., 2000, Preparation of enantio-specific epoxides. International Patent Application patent WO 00/73425 A1.
114. Straathof, A.J.J., Panke, S., and Schmid, A., 2002, The production of fine chemicals by biotransformations. Curr. Opin. Biotechnol., 13:548-556.
115. Studts, J.M., Mitchell, K.H., Pikus, J.D., McClay, K., Steffan, R.J., and Fox, B.G., 2000, Optimized expression and purification of toluene 4-monooxygenase hydroxylase. Protein Expr. Purif., 20:58-65.
116. Tao, Y., Bentley, W.E., and Wood, T.K., 2005, Phenol and 2-naphthol production by toluene 4-monooxygenases using two liquid phases. Appl. Microbiol. Biotechnol., 68:614-621.
117. Tao, Y., Bentley, W.E., and Wood, T.K., 2005, Regiospecific oxidation of naphthalene and flourene by toluene monooxygenases and engineered toluene 4-monooxygenase of Pseudomonas mendocina KR1. Biotechnol. Bioeng., 90:85-94.
118. Tao, Y., Fishman, A., Bentley, W.E., and Wood, T.K., 2004, Altering toluene 4-monooxygenase by active-site engineering for the synthesis of 3-methoxycatechol, methoxyhydroquinone, and methylhydroquinone. J. Bacteriol., 186:4705-4713.
119. Tao, Y., Fishman, A., Bentley, W.E., and Wood, T.K., 2004, Oxidation of benzene to phenol, catechol, and 1, 2, 3-trihydroxybenzene by toluene 4-monooxygenase of Pseudomonas mendocina KR1 and toluene 3-monooxygenase of Ralstonia pickettii PKO1. Appl. Environ. Microbiol., 70:3814-3820.
120. Tice, R., 1998, Review of toxicological literature, Pyrogallol 87-66-1. National Toxicology Program.
121. Umezawa, K., Kawakami, M., and Watanabe, T., 2003, Molecular design and biological activities of protein-tyrosine phosphatase inhibitors. Pharm. Ther., 99:15-24.
122. van Beilen, J.B., Duetz, W.A., Schmid, A., and Witholt, B., 2003, Practical issues in the application of oxygenases. Trends Biotechnol., 21:170-177.
123. van Hylckama Vlieg, J.E.T., and Janssen, D.B., 2001, Formation and detoxification of reactive intermediates in the metabolism of chlorinated ethenes. J. Biotechnol., 85:81-102.
124. Vardar, G., and Wood, T.K., 2005, Alpha subunit positions methionine 180 and glutamate 214 of Pseudomonas stutzeri OX1 toluene-o-xylene monooxygenase influence catalysis. J. Bacteriol., 187:1511-1514.
125. Vardar, G., Barbieri, P., andWood, T.K., 2005, Chemotaxis of Pseudomonas stutzeri OX1 and Burkholderia cepacia G4 toward chlorinated ethenes. Appl. Microbiol. Biotechnol., 66:696- 701.
126. Vardar, G., and Wood, T.K., 2005, Protein engineering of toluene-o-xylene monooxygenase from Pseudomonas stutzeri OX1 for enhanced chlorinated ethene degradation and o-xylene oxidation. Appl. Microbiol. Biotechnol., 68:510-517.
127. Vardar, G., Ryu, K., and Wood, T.K., 2005, Protein engineering of toluene-o-xylene monooxygenase from Pseudomonas stutzeri OX1 for oxidizing nitrobenzene to 3-nitrocatechol, 4- nitrocatehcol, and nitrohydroquinone. J. Biotechnol., 115:145-156.
128. Vardar, G., and Wood, T.K., 2004, Protein engineering of toluene-o-xylene monooxygenase from Pseudomonas stutzeri OX1 for synthesizing 4-methylresorcinol, methylhydroquinone, and pyrogallol. Appl. Environ. Microbiol., 70:3253-3262.
129. Vlieg, J.E.T.v.H., and Janssen, D.B., 2001, Formation and detoxification of reactive intermediates in the metabolism of chlorinated ethenes. J. Biotechnol., 85:81-102.
130. Westrick, J.J., Mello, J.W., and Thomas, R.F., 1984, The groundwater supply survey. J. Am. Water Works Assoc., 76:52-59.
131. Whited, G.M., and Gibson, D.T., 1991, Separation and partial characterization of the enzymes of the toluene-4-monooxygenase catabolic pathway in Pseudomonas mendocina KR1. J. Bacteriol., 173:3017-3020.
132. Wick, C.B., 1995, Genencor international takes a green route to blue dye. Genet. Eng. News, 15:22.
133. Xu, D., Ballou, D.P., and Massey, V., 2001, Studies of the mechanism of phenol hydroxylase: mutants Tyr289Phe, Asp54Asn, and Arg281Met. Biochem., 40:12369-12378.
134. Yen, K.-M., Karl, M.R., Blatt, L.M., Simon, M.J., Winter, R.B., Fausset, P.R., Lu, H.S., Harcourt, A.A., and Chen, K.K., 1991, Cloning and characterization of a Pseudomonas mendocina KR1 gene cluster encoding toluene-4-monooxygenase. J. Bacteriol., 173:5315-5327.
135. Yonezawa, T., March 2003, Capacitor electrolytes containing dihydroxytoluenes for low specific resistance. Japan patent 2, 003, 068, 585.