Biochemical and genetic analysis of the γ-resorcylate (2,6-dihydroxybenzoate) catabolic pathway in Rhizobium sp. strain MTP-10005: Identification and functional analysis of its gene cluster

Journal of Bacteriology

Volumn 189, Issue 5, 2007, Pages 1573-1581

  Yoshida, Masahiro ^a   Oikawa, Tadao ^a   Obata, Hitoshi ^a   Abe, Katsumasa ^b   Mihara, Hisaaki ^b   Esaki, Nobuyoshi ^b  

^a KANSAI UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA RESORCYLATE DECARBOXYLASE; GAMMA RESORCYLIC ACID; MALEYLACETATE REDUCTASE; OXYGENASE; REGULATOR PROTEIN; RESORCINOL HYDROXYLASE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GENE; BIOINFORMATICS; CATABOLISM; ESCHERICHIA COLI; GENE CLUSTER; GENE EXPRESSION REGULATION; GENE FUNCTION; GENE IDENTIFICATION; GRAA GENE; GRAB GENE; GRAC GENE; GRAD GENE; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; RHIZOBIUM;

BASE SEQUENCE; CLONING, MOLECULAR; ESCHERICHIA COLI; HYDROXYBENZOIC ACIDS; MOLECULAR SEQUENCE DATA; MULTIGENE FAMILY; OPERON; RHIZOBIUM;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; RHIZOBIUM SP.;

EID: 33947411285     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/JB.01675-06     Document Type: Article

References (39)

1. Alekshun, M. N., and S. B. Levy. 1999. Alteration of the repressor activity of MarR, the negative regulator of the Escherichia coli marRAB locus, by multiple chemicals in vitro. J. Bacteriol. 181:4669-4672.
2. Anderson, J. J., and S. Dagley. 1980. Catabolism of aromatic acids in Trichosporon cutaneum. J. Bacteriol. 141:534-543.
3. Andersen, J. J., and S. Dagley. 1981. Catabolism of tryptophan, anthranilate, and 2,3-dihydroxybenzoate in Trichosporon cutaneum. J. Bacteriol. 146:291-297.
4. Ariza, R. R., S. P. Cohen, N. Bachhawat, S. B. Levy, and B. Demple. 1994. Repressor mutations in the marRAB operon that activate oxidative stress genes and multiple antibiotic resistance in Escherichia coli. J. Bacteriol. 176:143-148.
5. Armengaud, J., K. N. Timmis, and R.-M. Wittich. 1999. A functional 4-hydroxysalicylate/hydroxyquinol degradative pathway gene cluster is linked to the initial dibenzo-p-dioxin pathway genes in Sphingomonas sp. strain RW1. J. Bacteriol. 181:3452-3461.
6. Ballou, D. P., B. Entsch, and L. J. Cole. 2005. Dynamics involved in catalysis by single-component and two-component flavin-dependent aromatic hydroxylases. Biochem. Biophys. Res. Commun. 338:590-598.
7. Bradford, M. M. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:248-254.
8. Buchan, A., E. L. Neidle, and M. A. Moran. 2004. Diverse organization of genes of the β-ketoadipate pathway in members of the marine Roseobacter lineage. Appl. Environ. Microbiol. 70:1658-1668.
9. Chapman, P. J., and D. W. Ribbons. 1976. Metabolism of resorcinylic compounds by bacteria: alternative pathways for resorcinol catabolism in Pseudomonas putida. J. Bacteriol. 125:985-998.
10. Cohen, S. P., H. Hächler, and S. B. Levy. 1993. Genetic and functional analysis of the multiple antibiotic resistance (mar) locus in Escherichia coli. J. Bacteriol. 175:1484-1492.
11. Collier, L. S., N. N. Nichols, and E. L. Neidle. 1997. benK encodes a hydrophobic permease-like protein involved in benzoate degradation by Acinetobacter sp. strain ADP1. J. Bacteriol. 179:5943-5946.
12. Daubaras, D. L., K. Saido, and A. M. Chakrabarty. 1996. Purification of hydroxyquinol 1,2-dioxygenase and maleylacetate reductase: the lower pathway of 2,4,5-trichlorophenoxyacetic acid metabolism by Burkholderia cepacia AC1100. Appl. Environ. Microbiol. 62:4276-4279.
13. Ferraroni, M., J. Seifert, V. M. Travkin, M. Thiel, S. Kaschabek, A. Scozzafava, L. Golovleva, M. Schlömann, and F. Briganti. 2005. Crystal structure of the hydroxyquinol 1,2-dioxygenase from Nocardioides simplex 3E, a key enzyme involved in polychlorinated aromatics biodegradation. J. Biol. Chem. 280:21144-21154.
14. Gaal, A., and H. Y. Neujahr. 1979. Metabolism of phenol and resorcinol in Trichosporon cutaneum. J. Bacteriol. 137:13-21.
15. Goto, M., H. Hayashi, I. Miyahara, K. Hirotsu, M. Yoshida, and T. Oikawa. 2006. Crystal structures of nonoxidative zinc-dependent 2,6-dihydroxybenzoate (γ-resorcylate) decarboxylase from Rhizobium sp. strain MTP-10005. J. Biol. Chem. 281:34365-34373.
16. Harpel, M. R., and J. D. Lipscomb. 1990. Gentisate 1,2-dioxygenase from Pseudomonas. Purification, characterization, and comparison of the enzymes from Pseudomonas testosteroni and Pseudomonas acidovorans. J. Biol. Chem. 265:6301-6311.
17. Huang, Y., K. X. Zhao, X. H. Shen, M. T. Chaudhry, C. Y. Jiang, and S. J. Liu. 2006. Genetic characterization of the resorcinol catabolic pathway in Corynebacterium glutamicum. Appl. Environ. Microbiol. 72:7238-7245.
18. Ishii, Y., Y. Narimatsu, Y. Iwasaki, N. Arai, K. Kino, and K. Kirimura. 2004. Reversible and nonoxidative gamma-resorcylic acid decarboxylase: characterization and gene cloning of a novel enzyme catalyzing carboxylation of resorcinol, 1,3-dihydroxybenzene, from Rhizobium radiobacter. Biochem. Biophys. Res. Commun. 324:611-620.
19. Iwagami, S. G., K. Yang, and J. Davies. 2000. Characterization of the protocatechuic acid catabolic gene cluster from Streptomyces sp. strain 2065. Appl. Environ. Microbiol. 66:1499-1508.
20. Kamath, A. V., and C. S. Vaidyanathan. 1990. New pathway for the biodegradation of indole in Aspergillus niger. Appl. Environ. Microbiol. 56:275-280.
21. Kluge, C., A. Tschech, and G. Fuchs. 1990. Anaerobic metabolism of resorcylic acids (m-dihydroxybenzoic acids) and resorcinol (1,3-benzenediol) in a fermenting and in a denitrifying bacterium. Arch. Microbiol. 155:68-74.
22. Laemmli, U. K. 1970. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227:680-685.
23. 2 by NAD(P)H-flavin oxidoreductase and 4-hydroxyphenylacetate 3-monooxygenase. Biochemistry 42:7509-7517.
24. Martin, R. G., and J. L. Rosner. 1995. Binding of purified multiple antibiotic-resistance repressor protein (MarR) to mar operator sequences. Proc. Natl. Acad. Sci. USA 92:5456-5460.
25. Matsui, T., T. Yoshida, T. Yoshimura, and T. Nagasawa. 2006. Regioselective carboxylation of 1,3-dihydroxybenzene by 2,6-dihydroxybenzoate decarboxylase of Pandoraea sp. 12B-2. Appl. Microbiol. Biotechnol. 73:95-102.
26. Otto, K., K. Hofstetter, M. Röthlisberger, B. Witholt, and A. Schmid. 2004. Biochemical characterization of StyAB from Pseudomonas sp. strain VLB120 as a two-component flavin-diffusible monooxygenase. J. Bacteriol. 186:5292-5302.
27. Parke, D., and L. N. Ornston. 1986. Enzymes of the β-ketoadipate pathway are inducible in Rhizobium and Agrobacterium spp. and constitutive in Bradyrhizobium spp. J. Bacteriol. 165:288-292.
28. Parke, D. 1995. Supraoperonic clustering of pca genes for catabolism of the phenolic compound protocatechuate in Agrobacterium tumefaciens. J. Bacteriol. 177:3808-3817.
29. Reid, J., R. D. Watson, J. B. Cochran, D. H. Sproull, B. E. Clayton, and F. T. Prunty. 1951. Sodium γ-resorcylate in rheumatic fever. Br. Med. J. 4727: 321-326.
30. Ruschig, H., J. Konig, D. Duwel, and H. Loewe. 1973. 2,6-Dihydroxybenzoic acid derivatives as anthelmintics. Arzneimittelforschung 23:1745-1785.
31. Seibert, V., K. Stadler-Fritzsche, and M. Schlömann. 1993. Purification and characterization of maleylacetate reductase from Alcaligenes eutrophus JMP134(pJP4). J. Bacteriol. 175:6745-6754.
32. Seibert, V., M. Thiel, I. S. Hinner, and M. Schlömann. 2004. Characterization of a gene cluster encoding the maleylacetate reductase from Ralstonia eutropha 335T, an enzyme recruited for growth with 4-fluorobenzoate. Microbiology 150:463-472.
33. Seoane, A. S., and S. B. Levy. 1995. Characterization of MarR, the repressor of the multiple antibiotic resistance (mar) operon in Escherichia coli. J. Bacteriol. 177:3414-3419.
34. Stolz, A., and H.-J. Knackmuss. 1993. Degradation of 2,4-dihydroxybenzoate by Pseudomonas sp. BN9. FEMS Microbiol. Lett. 108:219-224.
35. Tiedje, J. M., J. M. Duxbury, M. Alexander, and J. E. Dawson. 1969. 2,4-D metabolism: pathway of degradation of chlorophenols by Arthrobacter sp. J. Agric. Food Chem. 17:1021-1026.
36. Trefault, N., R. de la Iglesia, A. M. Molina, M. Manzano, T. Ledger, D. Perez-Pantoja, M. A. Sanchez, M. Stuardo, and B. Gonzalez. 2004. Genetic organization of the catabolic plasmid pJP4 from Ralstonia eutropha JMP134 (pJP4) reveals mechanisms of adaptation to chloroaromatic pollutants and evolution of specialized chloroaromatic degradation pathways. Environ. Microbiol. 6:655-668.
37. Vetting, M. W., and D. H. Ohlendorf. 2000. The 1.8 Å crystal structure of catechol 1,2-dioxygenase reveals a novel hydrophobic helical zipper as a subunit linker. Structure 8:429-440.
38. Yoshida, M., N. Fukuhara, and T. Oikawa. 2004. Thermophilic, reversible γ-resorcylate decarboxylase from Rhizobium sp. strain MTP-10005: purification, molecular characterization, and expression. J. Bacteriol. 186:6855-6863.
39. Yoshida, T., Y. Hayakawa, T. Matsui, and T. Nagasawa. 2004. Purification and characterization of 2,6-dihydroxybenzoate decarboxylase reversibly catalyzing nonoxidative decarboxylation. Arch. Microbiol. 181:391-397.