Protein engineering of the 4-methyl-5-nitrocatechol monooxygenase from Burkholderia sp. strain DNT for enhanced degradation of nitroaromatics

Applied and Environmental Microbiology

Volumn 72, Issue 6, 2006, Pages 3933-3939

  Leungsakul, Thammajun ^a,b,d   Johnson, Glenn R ^c   Wood, Thomas K ^a,b  

^a Texas AandM University   (United States)

^b TEXAS A AND M UNIVERSITY   (United States)

^c AIR FORCE RESEARCH LABORATORY   (United States)

^d THAMMASAT UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CATALYSIS; ENZYMES; MUTAGENESIS; NITROGEN COMPOUNDS; PHENOLS; SATURATION (MATERIALS COMPOSITION); SUBSTRATES;

FLAVOPROTEIN; NITRITE; NITROAROMATICS; PROTEIN ENGINEERING;

PROTEINS;

2 HYDROXY 5 METHYLQUINONE; 2,4 DINITROTOLUENE; 3 METHYL 4 NITROPHENOL; 4 METHYL 5 NITROCATECHOL MONOOXYGENASE; AMINO ACID; AROMATIC NITRO COMPOUND; FLAVOPROTEIN; ISOLEUCINE; LEUCINE; METHIONINE; NITRITE; NITROPHENOL; QUINONE DERIVATIVE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

BIODEGRADATION; ENZYME ACTIVITY; ORGANIC NITROGEN COMPOUND;

AMINO ACID SEQUENCE; ARTICLE; BACTERIAL STRAIN; BURKHOLDERIA; CATALYSIS; CATALYST; ENZYME ACTIVITY; ENZYME PURIFICATION; MICROBIAL DEGRADATION; MUTAGENESIS; NONHUMAN; NUCLEOTIDE SEQUENCE; POLYMERASE CHAIN REACTION; PROTEIN ENGINEERING; SEQUENCE ANALYSIS;

BACTERIAL PROTEINS; BASE SEQUENCE; BIODEGRADATION, ENVIRONMENTAL; BURKHOLDERIA; DNA PRIMERS; MIXED FUNCTION OXYGENASES; MOLECULAR SEQUENCE DATA; NITRITES; NITROPHENOLS; PROTEIN ENGINEERING; SUBSTRATE SPECIFICITY; VARIATION (GENETICS);

BURKHOLDERIA SP.;

EID: 33745154145     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/AEM.02966-05     Document Type: Article

References (31)

1. Bhushan, B., S. K. Samanta, A. Chauhan, A. K. Chakraborti, and R. K. Jain. 2000. Chemotaxis and biodegradation of 3-methyl-4-nitrophenol by Ralstonia sp. SJ98. Biochem. Biophys. Res. Commun. 275:129-133.
2. Brühlmann, F., and W. Chen. 1999. Tuning biphenyl dioxygenase for extended substrate specificity. Biotechnol. Bioeng. 63:544-551.
3. Cadwell, R. C., and G. F. Joyce. 1992. Randomization of genes by PCR mutagenesis. PCR Methods Appl. 2:28-33.
4. Canada, K. A., S. Iwashita, H. Shim, and T. K. Wood. 2002. Directed evolution of toluene ortho-monooxygenase for enhanced 1-naphthol synthesis and chlorinated ethene degradation. J. Bacteriol. 184:344-349.
5. Canyuk, B., P. J. Focia, and A. E. Eakin. 2001. The role for an invariant aspartic acid in hypoxanthine phosphoribosyltransferases is examined using saturation mutagenesis, functional analysis, and X-ray crystallography. Biochemistry 40:2754-2765.
6. Christopher, H. J., G. D. Boardman, and D. L. Freedman. 2000. Aerobic biological treatment of 2,4-dinitrotoluene in munitions plant wastewater. Water Res. 34:1595-1603.
7. Eaton, A. D., L. S. Clesceri, and A. E. Greenberg (ed.). 1995. Standard methods for the examination of water and wastewater. 19th ed. American Public Health Association, Washington, D.C.
8. Edelhoch, H. 1967. Spectroscopic determination of tryptophan and tyrosine in proteins. Biochemistry 6:1948-1954.
9. Farinas, E. T., U. Schwaneberg, A. Glieder, and F. H. Arnold. 2001. Directed evolution of a cytochrome P450 monooxygenase for alkane oxidation. Adv. Synth. Catal. 343:601-606.
10. Fortin, P. D., I. MacPherson, D. B. Neau, J. T. Bolin, and L. D. Eltis. 2005. Directed evolution of a ring-cleaving dioxygenase for polychlorinated biphenyl degradation. J. Biol. Chem. 280:42307-42314.
11. Haigler, B. E., S. F. Nishino, and J. C. Spain. 1994. Biodegradation of 4-methyl-5-nitrocatechol by Pseudomonas sp. strain DNT. J. Bacteriol. 176: 3433-3437.
12. Haigler, B. E., W.-C. Suen, and J. C. Spain. 1996. Purification and sequence analysis of 4-methyl-5-nitrocarechol oxygenase from Burkholderia sp. strain DNT. J. Bacteriol. 178:6019-6024.
13. Johnson, G. R., R. K. Jain, and J. C. Spain. 2002. Origins of the 2,4-dinitrotoluene pathway. J. Bacteriol. 184:4219-4232.
14. Kadiyala, V., B. F. Smets, K. Chandran, and J. C. Spain. 1998. High affinity p-nitrophenol oxidation by Bacillus sphaericus JS905. FEMS Microbiol. Lett. 166:115-120.
15. Kadiyala, V., and J. C. Spain. 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.
16. Keenan, B. G., T. Leungsakul, B. F. Smets, M. Mori, D. E. Henderson, and T. K. Wood. 2005. Protein engineering of the archetypal nitroarene dioxygenase of Ralstonia sp. strain U2 for activity on aminonitrotoluenes and dinitrotoluenes through alpha-subunit residues leucine 225, phenylalanine 350, and glycine 407. J. Bacteriol. 187:3302-3310.
17. Leungsakul, T., B. G. Keenan, H. Yin, B. F. Smets, and T. K. Wood. 2005. Saturation mutagenesis of 2,4-DNT dioxygenase of Burkholderia sp. strain DNT for enhanced dinitrotoluene degradation. Biotechnol. Bioeng. 92:416-426.
18. Malito, E., A. Alfieri, M. W. Fraaije, and A. Mattevi. 2004. Crystal structure of a Baeyer-Villiger monooxygenase. Proc. Natl. Acad. Sci. USA 101:13157-13162.
19. Meyer, A., A. Schmid, M. Held, A. H. Westphal, M. Röthlisberger, H.-P. E. Kohler, W. J. H. van Berkel, and B. Witholt. 2002. Changing the substrate reactivity of 2-hydroxybiphenyl 3-monooxygenase from Pseudomonas azelaica HBP1 by directed evolution. J. Biol. Chem. 277:5575-5582.
20. Meyer, A., M. Würsten, A. Schmid, H.-P. E. Kohler, and B. Witholt. 2002. Hydroxylation of indole by laboratory-evolved 2-hydroxybiphenyl 3-monooxygenase. J. Biol. Chem. 277:34161-34167.
21. Nishino, S. F., G. C. Paoli, and J. C. Spain. 2000. Aerobic degradation of dinitrotoluenes and pathway for bacterial degradation of 2,6-dinitrotoluene. Appl. Environ. Microbiol. 66:2139-2147.
22. Rui, L., Y. M. Kwon, A. Fishman, K. F. Reardon, and T. K. Wood. 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.
23. Sakamoto, T., J. M. Joern, A. Arisawa, and F. H. Arnold. 2001. Laboratory evolution of toluene dioxygenase to accept 4-picoline as a substrate. Appl. Environ. Microbiol. 67:3882-3887.
24. Sambrook, J., E. F. Fritsch, and T. Maniatis (ed.). 1989. Molecular cloning: a laboratory manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.
25. Sanger, F., S. Nicklen, and A. R. Coulson. 1977. DNA sequencing with chain-terminating inhibitors. Proc. Natl. Acad. Sci. USA 74:5463-5467.
26. Spain, J. C., and D. T. Gibson. 1991. Pathway for biodegradation of p-nitrophenol in a Moraxella sp. Appl. Environ. Microbiol. 57:812-819.
27. Spanggord, R. J., J. C. Spain, S. F. Nishino, and K. E. Mortelmans. 1991. Biodegradation of 2,4-dinitrotoluene by a Pseudomonas sp. Appl. Environ. Microbiol. 57:3200-3205.
28. Stemmer, W. P. C. 1994. DNA shuffling by random fragmentation and reassembly: in vitro recombination for molecular evolution. Proc. Natl. Acad. Sci. USA 91:10747-10751.
29. Suen, W.-C., and J. C. Spain. 1993. Cloning and characterization of Pseudomonas sp. strain DNT genes for 2,4-dinitrotoluene degradation. J. Bacteriol. 175:1831-1837.
30. van den Heuvel, R. H. H., W. A. M. van den Berg, S. Rovida, and W. J. H. van Berkel. 2004. Laboratory-evolved vanillyl-alconol oxidase produces natural vanillin. J. Biol. Chem. 279:33492-33500.
31. Zeyer, J., and H. P. Kocher. 1988. Purification and characterization of a bacterial nitrophenol oxygenase which converts ortho-nitrophenol to catechol and nitrite. J. Bacteriol. 170:1789-1794.