Protein engineering of toluene-o-xylene monooxygenase from Pseudomonas stutzeri OX1 for oxidizing nitrobenzene to 3-nitrocatechol, 4-nitrocatechol, and nitrohydroquinone

Journal of Biotechnology

Volumn 115, Issue 2, 2005, Pages 145-156

  Vardar, Gönül ^a   Ryu, Kang ^a   Wood, Thomas K ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

DNA shuffling; Saturation mutagenesis; Toluene o xylene monooxygenase

Indexed keywords

NITRO AROMATICS; NITROBENZENE;

AROMATIC HYDROCARBONS; DNA; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; TOLUENE;

PROTEINS;

3 NITROCATECHOL; 3 NITROPHENOL; 4 NITROPHENOL; AGAR; BACTERIAL ENZYME; CATECHOL DERIVATIVE; NITRO DERIVATIVE; NITROBENZENE; NITROHYDROQUINONE; OXYGENASE; PARA CRESOL; TOLUENE; TOLUENE OXYLENE MONOOXYGENASE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ARTICLE; BACTERIAL CELL; BACTERIAL METABOLISM; BACTERIUM MUTANT; BURKHOLDERIA CEPACIA; DNA SHUFFLING; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME SPECIFICITY; ESCHERICHIA COLI; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MUTAGENESIS; NONHUMAN; OXIDATION; PRIORITY JOURNAL; PROTEIN ENGINEERING; PROTEIN SYNTHESIS; PSEUDOMONAS MENDOCINA; PSEUDOMONAS STUTZERI; STRAIN DIFFERENCE; WILD TYPE;

CATECHOLS; DNA SHUFFLING; ENZYME ACTIVATION; ESCHERICHIA COLI; GENETIC ENHANCEMENT; HYDROQUINONES; MUTAGENESIS, SITE-DIRECTED; NITROBENZENES; OXIDATION-REDUCTION; OXYGENASES; PROTEIN ENGINEERING; PSEUDOMONAS STUTZERI; RECOMBINANT PROTEINS;

BURKHOLDERIA; BURKHOLDERIA CEPACIA; ESCHERICHIA COLI; PSEUDOMONAS; PSEUDOMONAS MENDOCINA; PSEUDOMONAS STUTZERI;

EID: 10644230021     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2004.08.008     Document Type: Article

References (48)

1. Y. Abe, M. Takeo, and S. Negoro Biodegradation of nitrophenols by Rhodococcus sp. strain PN1 Mizu Shori Gijutsu 43 2002 615 621
2. H. Akiyoshi, N. Toriu, and A. Sugino Electrophotographic Photoreceptor Containing Hydroquinones, its Manufacture, and Electrophotographic Apparatus (JP 2000075514) 2000 Ricoh Co. Ltd Japan
3. F.H. Arnold When blind is better: protein design by evolution Nat. Biotechnol. 16 1998 617 618
4. F.H. Arnold, and J.C. Moore Optimizing industrial enzymes by directed evolution Adv. Biochem. Eng./Biotechnol. 1997 58
5. G. Bertoni, F. Bolognese, E. Galli, and P. Barbieri 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 1996 3704 3711
6. J. Borgulya, H. Bruderer, K. Bernauer, G. Zuercher, and M. Da Prada Catechol-o-methyltransferase-inhibiting pyrocatechol derivatives: synthesis and structure-activity studies Helvetica Chim. Acta 72 1989 952 968
7. V. Cafaro, R. Scognamiglio, A. Viggiani, V. Izzo, I. Passaro, E. Notomista, F.D. Piaz, A. Amoresano, A. Casbarra, P. Pucci, and A.D. Donato Expression and purification of the recombinant subunits of toluene/o-xylene monooxygenase and reconstitution of the active complex Eur. J. Biochem. 269 2002 5689 5699
8. K.A. Canada, S. Iwashita, H. Shim, and T.K. Wood Directed evolution of toluene ortho-monooxygenase for enhanced 1-naphthol synthesis and chlorinated ethene degradation J. Bacteriol. 184 2002 344 349
9. S. Chauhan, P. Barbieri, and T.K. Wood Oxidation of trichloroethylene, 1,1-dichloroethylene, and chloroform by toluene/o-xylene monooxygenase from Pseudomonas stutzeri OX1 Appl. Environ. Microbiol. 64 1998 3023 3024
10. J.F. Corbett Relation between color and structure for simple nitro dyes J. Soc. Dyers Colourists 83 1967 273 276
11. S. El Fantroussi, R. Giot, H. Naveau, and S.N. Agathos Acclimation of a methanogenic consortium to a mixture of hydroxylated aromatic compounds Chemosphere 36 1998 1575 1583
12. M.D. Ennis, and N.B. Ghazal The Synthesis of (+)- and (-)-Flesinoxan: application of enzymatic resolution methodology Tetrahedron Lett. 33 1992 6287 6290
13. A. Fishman, Y. Tao, W.E. Bentley, and T.K. Wood Protein engineering of toluene 4-monooxygenase of Pseudomonas mendocina KR1 for synthesizing 4-nitrocatechol from nitrobenzene Biotechnol. Bioeng. 87 2004 779 790
14. A. Fishman, Y. Tao, and T.K. Wood Toluene 3-monooxygenase of Ralstonia pickettii PKO1 is a para-hydroxylating enzyme J. Bacteriol. 186 2004 3117 3123
15. N. Guex, A. Diemand, and M.C. Peitsch Protein modeling for all Trends Biotechnol. 24 1999 364 367
16. N. Guex, and M.C. Peitsch SWISS-MODEL and the Swiss-PdbViewer: an environment for comparative protein modeling Electrophoresis 18 1997 2714 2723
17. B.E. Haigler, and J.C. Spain Biotransformation of nitrobenzene by bacteria containing toluene degradative pathways Appl. Environ. Microbiol. 57 1991 3156 3162
18. P. Hamel, and Y. Girard Synthesis of dephostatin, a novel protein tyrosine phosphatase inhibitor Tetrahedron Lett. 35 1994 8101 8102
19. Z. He, and J.C. Spain A novel 2-aminomuconate deaminase in the nitrobenzene degradation pathway of Pseudomonas pseudoalcaligenes JS45 J. Bacteriol. 180 1998 2502 2506
20. H. Joo, Z. Lin, and F.H. Arnold Laboratory evolution of peroxide-mediated cytochrome P450 hydroxylation Nature 399 1999 670 673
21. K. Karim, and S.K. Gupta Continuous biotransformation and removal of nitrophenols under denitrifying conditions Water Res. 37 2003 2953 2959
22. J. Kieboom, H. Van den Brink, J. Frankena, and J.A.M. De Bont Production of 3-nitrocatechol by oxygenase-containing bacteria: optimization of the nitrobenzene biotransformation by Nocardia S3 Appl. Microbiol. Biotechnol. 55 2001 290 295
23. L. Krab-Husken Production of Catechols: Microbiology and Technology 2002 Wageningen University Netherlands
24. D.A. Learmonth, and A.P. Freitas Chemical synthesis and characterization of conjugates of a novel catechol-o-methyltransferase inhibitor Bioconjug. Chem. 13 2002 1112 1118
25. D.A. Learmonth, M.A. Vieira-Coelho, J. Benes, P.C. Alves, N. Borges, A.P. Freitas, and P. Soares-da-Silva 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 2002 685 695
26. K.H. Mitchell, J.M. Studts, and B.G. Fox Combined participation of hydroxylase active site residues and effector protein binding in a para to ortho modulation of toluene 4-monooxygenase regiospecificity Biochemistry 41 2002 3176 3188
27. Y.S. Oh, Y.H. Lee, J.H. Lee, and S.C. Choi Characteristics of nitrobenzene degradation by Mycobacterium chelonae strain NB01 J. Microbiol. Biotechnol. 13 2003 309 312
28. A. Palumbo, A. Napolitano, and M. d'Ischia 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 2002 13 16
29. R.E. Parales, T.A. Ontl, and D.T. Gibson Cloning and sequence analysis of a catechol 2,3-dioxygenase gene from the nitrobenzene-degrading strain Comamonas sp JS765 J. Ind. Microbiol. Biotechnol. 19 1997 385 391
30. M.C. Peitsch Protein modeling by e-mail Bio/Technology 13 1995 658 660
31. J.D. Pikus, J.M. Studts, K. McClay, R.J. Steffan, and B.G. Fox Changes in the regiospecificity of aromatic hydroxylation produced by active site engineering in the diiron enzyme toluene 4-monooxygenase Biochemistry 36 1997 9283 9289
32. J.D. Pikus, K.H. Mitchell, J.M. Studts, K. McClay, R.J. Steffan, and B.G. Fox Threonine 201 in the diiron enzyme toluene 4-monooxygenase is not required for catalysis Biochemistry 39 2000 791 799
33. A.C. Rosenzweig, H. Brandstetter, D.A. Whittington, P. Nordlund, S.J. Lippard, and C.A. Frederick Crystal structures of the methane monooxygenase hydroxylase from Methylococcus capsulatus (Bath): implications for substrate gating and component interactions Proteins Struct. Funct. Genet. 29 1997 141 152
34. L. Rui, Y.M. Kwon, A. Fishman, K.F. Reardon, and T.K. Wood Saturation mutagenesis of toluene ortho-monooxygenase from Burkholderia cepacia G4 for enhanced 1-naphthol synthesis and chloroform degradation Appl. Environ. Microbiol. 70 2004 3246 3252
35. Rui, L., Reardon, K. F., Wood, T. K., in press. Protein engineering of toluene ortho-monooxygenase of Burkholderia cepacia G4 for regiospecific hydroxylation of indole to form various indigoid compounds. Appl. Microbiol. Biotechnol.
36. D. Ryoo, H. Shim, K. Canada, P. Barbieri, and T.K. Wood Aerobic degradation of tetrachloroethylene by toluene-o-xylene monooxygenase of Pseudomonas stutzeri OX1 Nat. Biotechnol. 18 2000 775 778
37. J. Sambrook, E.F. Fritsch, and T. Maniatis Molecular Cloning, A Laboratory Manual 1989 Cold Spring Harbor Laboratory Press Cold Spring Harbor, NY
38. F. Sanger, S. Nicklen, and A.R. Coulson DNA sequencing with chain-terminating inhibitors Proc. Natl. Acad. Sci. 74 1977 5463 5467
39. T. Schwede, J. Kopp, N. Guex, and M.C. Peitsch SWISS-MODEL: an automated protein homology-modeling server Nucleic Acid Res. 31 2003 3381 3385
40. J.C. Spain, and D.T. Gibson Pathway for biodegradation of p-nitrophenol in a Moraxella sp Appl. Environ. Microbiol. 57 1991 812 819
41. W.P.C. Stemmer DNA shuffling by random fragmentation and reassembly: in vitro recombination for molecular evolution Proc. Natl. Acad. Sci. 91 1994 10747 10751
42. Y. Tao, A. Fishman, W.E. Bentley, and T.K. Wood Altering toluene 4-monooxygenase by active-site engineering for the synthesis of 3-methoxycatechol, methoxyhydroquinone, and methylhydroquinone J. Bacteriol. 186 2004 4705 4713
43. K. Umezawa, M. Kawakami, and T. Watanabe Molecular design and biological activities of protein-tyrosine phosphatase inhibitors Pharmacol. Ther. 99 2003 15 24
44. J.B. van Beilen, W.A. Duetz, and B. Witholt Practical issues in the application of oxygenases Trends Biotechnol. 21 2003 170 177
45. G. Vardar, and T.K. Wood Protein engineering of toluene-o-xylene monooxygenase from Pseudomonas stutzeri OX1 for synthesizing 4-methylresorcinol, methylhydroquinone, and pyrogallol Appl. Environ. Microbiol. 70 2004 3253 3262
46. Y. Yamada Capacitor Electrolyte Solution Containing A Hydrogen Absorber (JP 02054921) 1990 Nichicon Corp. Japan
47. J. Zeyer, H.P. Kocher, and K.N. Timmis Influence of para-substituents on the oxidative metabolism of o-nitrophenols by Pseudomonas putida B2 Appl. Environ. Microbiol. 52 1986 334 339
48. J.S. Zhao, and O.P. Ward Cometabolic biotransformation of nitrobenzene by 3-nitrophenol degrading Pseudomonas putida 2NP8 Can. J. Microbiol. 46 2000 643 652