Conversion of 3-chlorocatechol by various catechol 2,3-dioxygenases and sequence analysis of the chlorocatechol dioxygenase region of Pseudomonas putida GJ31

Journal of Bacteriology

Volumn 181, Issue 4, 1999, Pages 1309-1318

  Mars, Astrid E ^a   Kingma, Jaap ^a   Kaschabek, Stefan R ^b   Reineke, Walter ^b   Janssen, Dick B ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY OF WUPPERTAL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3 CHLOROCATECHOL; BACTERIAL ENZYME; CATECHOL 2,3 DIOXYGENASE; CATECHOL DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BACTERIAL METABOLISM; CARBOXY TERMINAL SEQUENCE; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INACTIVATION; ENZYME SPECIFICITY; ENZYME SUBSTRATE; GENE LOCUS; MOLECULAR CLONING; NONHUMAN; NUCLEOTIDE SEQUENCE; OPEN READING FRAME; PLASMID; PRIORITY JOURNAL; PSEUDOMONAS PUTIDA; SEQUENCE ANALYSIS;

PSEUDOMONAS PUTIDA;

EID: 0033064439     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/jb.181.4.1309-1318.1999     Document Type: Article

References (55)

1. Altschul, S. F., T. L. Madden, A. A. Schäffer, J. Zhang, Z. Zhang, W. Miller, and D. J. Lipman. 1997. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Res. 25:3389-3402.
2. Arensdorf, J. J., and D. D. Focht. 1994. Formation of chlorocatechol meta cleavage products by a pseudomonad during metabolism of monochlorobiphenyls. Appl. Environ. Microbiol. 60:2884-2889.
3. Assinder, S. J., and P. A. Williams. 1990. The TOL plasmids: determinants of the catabolism of toluene and the xylenes. Adv. Microb. Physiol. 31:1-69.
4. Ausubel, F. M., R. Brent, R. E. Kingston, D. D. Moore, J. G. Seidman, J. A. Smith, and K. Struhl. 1994. Current protocols in molecular biology. Green Publishing Associates, Inc., New York, N.Y.
5. Bartels, I., H.-J. Knackmuss, and W. Reineke. 1984. Suicide inactivation of catechol 2,3-dioxygenase from Pseudomonas putida mt-2 by 3-halocatechols. Appl. Environ. Microbiol. 47:500-505.
6. Cerdan, P., M. Rekik, and S. Harayama. 1995. Substrate specificity differences between two catechol 2,3-dioxygenases encoded by the TOL and NAH plasmids from Pseudomonas putida. Eur. J. Biochem. 229:113-118.
7. Dehmel, U. Personal communication.
8. Duetz, W. A., M. K. Winson, J. G. van Andel, and P. A. Williams. 1991. Mathematical analysis of catabolic function loss in a population of Pseudomonas putida mt-2 during non-limited growth on benzoate. J. Gen. Microbiol. 137:1363-1368.
9. Eltis, L. D., and J. T. Bolin. 1996. Evolutionary relationships among extradiol dioxygenases. J. Bacteriol. 178:5930-5937.
10. Haigler, B. E., and J. C. Spain. 1989. Degradation of p-chlorotoluene by a mutant of Pseudomonas sp. strain JS6. Appl. Environ. Microbiol. 55:372-379.
11. Han, S., L. D. Eltis, K. N. Timmis, S. W. Muchmore, and J. T. Bolin. 1995. Crystal structure of the biphenyl-cleaving extradiol dioxygenase from a PCB-degrading pseudomonad. Science 270:976-980.
12. Harayama, S., A. Polissi, and M. Rekik. 1991. Divergent evolution of chloroplast-type ferredoxins. FEBS Lett. 285:85-88.
13. Higson, F. K., and D. D. Focht. 1992. Utilization of 3-chloro-2-methylbenzoic acid by Pseudomonas cepacia MB2 through the meta fission pathway. Appl. Environ. Microbiol. 58:2501-2504.
14. Hofer, B., L. D. Eltis, D. N. Dowling, and K. N. Timmis. 1993. Genetic analysis of a Pseudomonas locus encoding a pathway for biphenyl/polychlorinated biphenyl degradation. Gene 130:47-55.
15. Hollender, J., W. Dott, and J. Hopp. 1994. Regulation of chloro-and methylphenol degradation in Comamonas testosteroni JH5. Appl. Environ. Microbiol. 60:2330-2338.
16. Hugo, N., J. Armengaud, J. Gaillard, K. N. Timmis, and Y. Jouanneau. 1998. A novel [2Fe-2S] ferredoxin from Pseudomonas putida mt2 promotes the reductive reactivation of catechol 2,3-dioxygenase. J. Biol. Chem. 273:9622-9629.
17. Johnson, G. R., and R. H. Olsen. 1995. Nucleotide sequence analysis of genes encoding a toluene/benzene-2-monooxygenase from Pseudomonas sp. strain JS150. Appl. Environ. Microbiol. 61:3336-3346.
18. Kado, C. I., and S.-T. Liu. 1981. Rapid procedure for detection and isolation of large and small plasmids. J. Bacteriol. 145:1365-1373.
19. Kaschabek, S. R., T. Kasberg, D. Müller, A. E. Mars, D. B. Janssen, and W. Reineke. 1998. Degradation of chloroaromatics: purification and characterization of a novel type of chlorocatechol 2,3-dioxygenase of Pseudomonas putida GJ31. J. Bacteriol. 180:296-302.
20. Keil, H., M. R. Lebens, and P. A. Williams. 1985. TOL plasmid pWW15 contains two nonhomologous, independently regulated catechol 2,3-oxygenase genes. J. Bacteriol. 163:248-255.
21. Kitayama, A., T. Achioku, T. Yanagawa, K. Kanou, M. Kikuchi, H. Ueda, E. Suzuki, H. Nishimura, T. Nagamune, and Y. Kawakami. 1996. Cloning and characterization of extradiol aromatic ring-cleavage dioxygenases of Pseudomonas aeruginosa J1104. J. Ferment. Bioeng. 82:217-223.
22. Klečka, G. M., and D. T. Gibson. 1981. Inhibition of catechol 2,3-dioxygenase from Pseudomonas putida by 3-chlorocatechol. Appl. Environ. Microbiol. 41:1159-1165.
23. Kukor, J. J., and R. H. Olsen. 1996. Catechol 2,3-dioxygenases functional in oxygen-limited (hypoxic) environments. Appl. Environ. Microbiol. 62:1728-1740.
24. Lendenmann, U., and J. C. Spain. 1996. 2-Aminophenol 1,6-dioxygenase: a novel aromatic ring cleavage enzyme purified from Pseudomonas pseudoalcaligenes JS45. J. Bacteriol. 178:6227-6232.
25. Mars, A. E., T. Kasberg, S. R. Kaschabek, M. H. van Agteren, D. B. Janssen, and W. Reineke. 1997. Microbial degradation of chloroaromatics: use of the meta-cleavage pathway for mineralization of chlorobenzene. J. Bacteriol. 179:4530-4537.
26. Mars, A. E., G. T. Prins, P. Wietzes, W. de Koning, and D. B. Janssen. 1998. Effect of trichloroethylene on the competitive behavior of toluene-degrading bacteria. Appl. Environ. Microbiol. 64:208-215.
27. McClure, N. C., and W. A. Venables. 1986. Adaptation of Pseudomonas putida mt-2 to growth on aromatic amines. J. Gen. Microbiol. 132:2209-2218.
28. Mitraki, A., and J. King. 1989. Protein folding intermediates and inclusion body formation. Biotechnology 7:690-697.
29. Murray, V. 1989. Improved double-stranded DNA sequencing using the linear polymerase chain reaction. Nucleic Acids Res. 17:8889.
30. Nakai, C., K. Huri, H. Kagamiyama, T. Makazawa, and M. Nozaki. 1983. Purification, subunit structure, and partial amino acid sequence of metapyrocatechase. J. Biol. Chem. 258:2916-2922.
31. Nakai, C., H. Kagamiyama, M. Nozaki. T. Nakazawa, S. Inouye, Y. Ebina, and A. Nakazawa. 1983. Complete nucleotide sequence of the metapyrocatechase gene on the TOL plasmid of Pseudomonas putida mt-2. J. Biol. Chem. 258:2923-2928.
32. Nelson, M. J. K., S. O. Montgomery, O. J. O'Neill, and P. H. Pritchard. 1986. Aerobic metabolism of trichloroethylene by a bacterial isolate. Appl. Environ. Microbiol. 52:383-384.
33. Newman, L. M., and L. P. Wackett. 1995. Purification and characterization of toluene 2-monooxygenase from Burkholderia cepacia G4. Biochemistry 34: 14066-14076.
34. Nordlund, I., J. Powlowski, and V. Shingler. 1990. Complete nucleotide sequence and polypeptide analysis of multicomponent phenol hydroxylase from Pseudomonas sp. strain CF600. J. Bacteriol. 172:6826-6833.
35. Nordlund, I., and V. Shingler. 1990. Nucleotide sequences of the meta-cleavage pathway enzymes 2-hydroxymuconic semialdehyde dehydrogenase and semialdehyde hydrolase from Pseudomonas CF600. Biochim. Biophys. Acta 1049:227-230.
36. Oh, J. M., E. Kang, K. R. Min, C.-K. Kim, Y.-C. Kim, J.-Y. Lim, K.-S. Lee, K.-H. Min, and Y. Kim. 1997. Structure of catechol 2,3-dioxygenase gene encoded in TOM plasmid of Pseudomonas putida G4. Biochem. Biophys. Res. Commun. 234:578-581.
37. Polissi, A., and S. Harayama. 1993. In vivo reactivation of catechol 2,3-dioxygenase mediated by a chloroplast-type ferredoxin: a bacterial strategy to expand the substrate specificity of aromatic degradative pathways. EMBO J. 12:3339-3347.
38. Powlowski, J., and V. Shingler. 1994. Genetics and biochemistry of phenol degradation by Pseudomonas sp. CF600. Biodegradation 5:219-236.
39. Saint, C. P., N. C. McClure, and W. A. Venables. 1990. Physical map of the aromatic amine and m-toluate catabolic plasmid pTDN1 in Pseudomonas putida: localization of a unique meta-cleavage pathway. J. Gen. Microbiol. 136:615-625.
40. Sala-Trepat, J. M., and W. C. Evans. 1971. The meta cleavage of catechol by Azotobacter species. 4-Oxalocrotonate pathway. Eur. J. Biochem. 20:400-413.
41. Sala-Trepat, J. M., K. Murray, and P. A. Williams. 1972. The metabolic divergence in the meta cleavage of catechols by Pseudomonas putida NCIB 10015. Physiological significance and evolutionary implications. Eur. J. Biochem. 28:347-356.
42. Schanstra, J. P., R. Rink, F. Pries, and D. B. Janssen. 1993. Construction of an expression and site-directed mutagenesis system of haloalkane dehalogenase in Escherichia coli. Protein Expression Purif. 4:479-489.
43. Schlömann, M. 1994. Evolution of chlorocatechol catabolic pathways. Biodegradation 5:301-321.
44. Senda, T., K. Sugiyama, H. Narita, T. Yamamoto, K. Kimbara, M. Fukuda, M. Sato, K. Yano, and Y. Mitsui. 1996. Three-dimensional structures of free form and two substrate complexes of an extradiol ring-cleavage type dioxygenase, the BphC enzyme from Pseudomonas sp. strain KKS102. J. Mol. Biol. 255:735-752.
45. Shields, M. S., S. O. Montgomery, S. M. Cuskey, P. J. Chapman, and P. H. Pritchard. 1991. Mutants of Pseudomonas cepacia G4 defective in catabolism of aromatic compounds and trichloroethylene. Appl. Environ. Microbiol. 57:1935-1941.
46. Shine, J., and L. Dalgarno. 1975. Determinant of cistron specificity in bacterial ribosomes. Nature 254:34-38.
47. Smith, M. R. 1990. The biodegradation of aromatic hydrocarbons by bacteria. Biodegradation 1:191-206.
48. Studier, F. W., A. H. Rosenberg, J. J. Dunn, and J. W. Dubendorff. 1990. Use of T7 RNA polymerase to direct expression of cloned genes. Methods Enzymol. 185:60-89.
49. Wallis, M. G., and S. K. Chapman. 1990. Isolation and partial characterization of an extradiol non-haem iron dioxygenase which preferentially cleaves 3-methylcatechol. Biochem. J. 266:605-609.
50. Wasserfallen, A., M. Rekik, and S. Harayama. 1991. A Pseudomonas putida strain able to degrade m-toluate in the presence of 3-chlorocatechol. Biotechnology 9:296-298.
51. Williams, P. A., S. J. Assinder, and L. E. Shaw. 1990. Construction of hybrid xylE genes between the two duplicate homologous genes from TOL plasmid pWW53: comparison of the kinetic properties of the gene products. J. Gen. Microbiol. 136:1583-1589.
52. Williams, P. A., and J. R. Sayers. 1994. The evolution of pathways for aromatic hydrocarbon oxidation in Pseudomonas. Biodegradation 5:195-217.
53. Yanisch-Perron, C., J. Vieira, and J. Messing. 1985. Improved M13 phage cloning vectors and host strains: nucleotide sequences of M13mp18 and pUC19. Gene 33:103-109.
54. Yolov, A. A., and Z. A. Shabarova. 1990. Constructing DNA by polymerase recombination. Nucleic Acids Res. 18:3983-3986.
55. Yrjälä, K., L. Paulin, and M. Romantschuk. 1997. Novel organisation of catechol meta-pathway genes in Sphingomonas sp. HV3 pSKY4 plasmid. FEMS Microbiol. Lett. 154:403-408.