Reduction kinetics of 3-hydroxybenzoate 6-hydroxylase from Rhodococcus jostii RHA1

Biochemistry

Volumn 51, Issue 21, 2012, Pages 4309-4321

  Sucharitakul, Jeerus ^a   Wongnate, Thanyaporn ^b   Montersino, Stefania ^c   Van Berkel, Willem J H ^c   Chaiyen, Pimchai ^b  

^a CHULALONGKORN UNIVERSITY   (Thailand)

^b MAHIDOL UNIVERSITY   (Thailand)

^c WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ANAEROBIC CONDITIONS; AROMATIC LIGANDS; BIMOLECULAR RATE CONSTANTS; ENZYME-LIGAND COMPLEX; ENZYME-SUBSTRATE COMPLEXES; FREE ENZYME; GENTISATE; IRREVERSIBLE REDUCTION; KINETIC DERIVATION; LIMITING VALUES; MONOOXYGENASES; NICOTINAMIDE ADENINE DINUCLEOTIDES; RATE ENHANCEMENT; REDUCTION KINETICS; REDUCTION MECHANISMS; REDUCTION RATE; RHODOCOCCUS; SATURATING CONCENTRATION; STOPPED FLOW; THERMODYNAMIC DRIVING FORCES;

AMIDES; AROMATIC COMPOUNDS; COMPLEXATION; DEGRADATION; ENZYMES; KINETICS; NUCLEAR FUELS;

RATE CONSTANTS;

3 HYDROXYBENZOATE 6 HYDROXYLASE; 3 HYDROXYBENZOIC ACID; BACTERIAL ENZYME; GENTISIC ACID; NICOTINAMIDE ADENINE DINUCLEOTIDE; OXYGENASE; QUERCETIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; UNCLASSIFIED DRUG;

ANAEROBIC METABOLISM; ARTICLE; CATALYSIS; CONCENTRATION (PARAMETERS); ENZYMATIC DEGRADATION; ENZYME SUBSTRATE COMPLEX; HYDROXYLATION; ISOMERIZATION; NONHUMAN; PH; PRIORITY JOURNAL; REDUCTION KINETICS; RHODOCOCCUS; RHODOCOCCUS JOSTII; SPECTROPHOTOMETRY; STIMULATION; THERMODYNAMICS;

BACTERIAL PROTEINS; KINETICS; LIGANDS; MIXED FUNCTION OXYGENASES; NAD; OXIDATION-REDUCTION; RHODOCOCCUS; SUBSTRATE SPECIFICITY; THERMODYNAMICS;

RHODOCOCCUS JOSTII;

EID: 84861617028     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi201823c     Document Type: Article

References (46)

1. Díaz, E. (2004) Bacterial degradation of aromatic pollutants: A paradigm of metabolic versatility Int. Microbiol. 7, 173-180
2. Olaniran, A. O. and Igbinosa, E. O. (2011) Chlorophenols and other related derivatives of environmental concern: Properties, distribution and microbial degradation processes Chemosphere 83, 1297-1306
3. Lu, X. Y., Zhang, T., and Fang, H. H. (2011) Bacteria-mediated PAH degradation in soil and sediment Appl. Microbiol. Biotechnol. 89, 1357-1371
4. Andreoni, V. and Gianfreda, L. (2007) Bioremediation and monitoring of aromatic-polluted habitats Appl. Microbiol. Biotechnol. 76, 287-308
5. Harwood, C. S. and Parales, R. E. (1996) The β-ketoadipate pathway and the biology of self-identity Annu. Rev. Microbiol. 50, 553-590
6. Larkin, M. J., Kulakov, L. A., and Allen, C. C. (2006) Biodegradation by members of the genus Rhodococcus: Biochemistry, physiology, and genetic adaptation Adv. Appl. Microbiol. 59, 1-29
7. Bell, K. S., Philp, J. C., Aw, D. W., and Christofi, N. (1998) The genus Rhodococcus J. Appl. Microbiol. 85, 195-210
8. de Carvalho, C. C. and da Fonseca, M. M. (2005) The remarkable Rhodococcus erythropolis Appl. Microbiol. Biotechnol. 67, 715-726
9. McLeod, M. P., Warren, R. L., Hsiao, W. W., Araki, N., Myhre, M., Fernandes, C., Miyazawa, D., Wong, W., Lillquist, A. L., Wang, D., Dosanjh, M., Hara, H., Petrescu, A., Morin, R. D., Yang, G., Stott, J. M., Schein, J. E., Shin, H., Smailus, D., Siddiqui, A. S., Marra, M. A., Jones, S. J., Holt, R., Brinkman, F. S., Miyauchi, K., Fukuda, M., Davies, J. E., Mohn, W. W., and Eltis, L. D. (2006) The complete genome of Rhodococcus sp. RHA1 provides insights into a catabolic powerhouse Proc. Natl. Acad. Sci. U.S.A. 103, 15582-15587
10. Liu, T.-T., Xu, Y., Liu, H., Luo, S., Yin, Y. J., Liu, S. J., and Zhou, N. Y. (2011) Functional characterization of a gene cluster involved in gentisate catabolism in Rhodococcus sp. strain NCIMB 12038 Appl. Microbiol. Biotechnol. 90, 671-678
11. Montersino, S. and van Berkel, W. J. (2011) Functional annotation and characterization of 3-hydroxybenzoate 6-hydroxylase from Rhodococcus jostii RHA1 Biochim. Biophys. Acta 1824, 433-442
12. van Berkel, W. J., Kamerbeek, N. M., and Fraaije, M. W. (2006) Flavoprotein monooxygenases, a diverse class of oxidative biocatalysts J. Biotechnol. 124, 670-689
13. Entsch, B. and van Berkel, W. J. (1995) Structure and mechanism of p -hydroxybenzoate hydroxylase FASEB J. 9, 476-483
14. Entsch, B., Cole, L. J., and Ballou, D. P. (2005) Protein dynamics and electrostatics in the function of p -hydroxybenzoate hydroxylase Arch. Biochem. Biophys. 433, 297-311
15. Palfey, B. A. and McDonald, C. A. (2010) Control of catalysis in flavin-dependent monooxygenases Arch. Biochem. Biophys. 493, 26-36
16. Chaiyen, P. (2010) Flavoenzymes catalyzing oxidative aromatic ring-cleavage reactions Arch. Biochem. Biophys. 493, 62-70
17. Palfey, B. A., Ballou, D. P., and Massey, V. (1995) Oxygen Activation by Flavins and Pterins. In Active Oxygen Species in Biochemistry (Liebman, J. F. and Greenberg, A., Eds.) pp 37-83, Chapman Hall, Glasgow, Scotland.
18. Ballou, D. P., Entsch, B., and Cole, L. J. (2005) Dynamics involved in catalysis by single-component and two-component flavin-dependent aromatic hydroxylases Biochem. Biophys. Res. Commun. 338, 590-598
19. Wang, L. H., Hamzah, R. Y., Yu, Y. M., and Tu, S. C. (1987) Pseudomonas cepacia 3-hydroxybenzoate 6-hydroxylase: Induction, purification, and characterization Biochemistry 26, 1099-1104
20. Liu, D. Q., Liu, H., Gao, X. L., Leak, D. J., and Zhou, N. Y. (2005) Arg169 is essential for catalytic activity of 3-hydroxybenzoate 6-hydroxylase from Klebsiella pneumoniae M5a1 Microbiol. Res. 160, 53-59
21. Gao, X., Tan, C. L., Yeo, C. C., and Poh, C. L. (2005) Molecular and biochemical characterization of the xlnD -encoded 3-hydroxybenzoate 6-hydroxylase involved in the degradation of 2,5-xylenol via the gentisate pathway in Pseudomonas alcaligenes NCIMB 9867 J. Bacteriol. 187, 7696-7702
22. Park, M., Jeon, Y., Jang, H. H., Ro, H. S., Park, W., Madsen, E. L., and Jeon, C. O. (2007) Molecular and biochemical characterization of 3-hydroxybenzoate 6-hydroxylase from Polaromonas naphthalenivorans CJ2 Appl. Environ. Microbiol. 73, 5146-5152
23. Yang, Y.-F., Zhang, J. J., Wang, S. H., and Zhou, N. Y. (2010) Purification and characterization of the ncgl2923 -encoded 3-hydroxybenzoate 6-hydroxylase from Corynebacterium glutamicum J. Basic Microbiol. 50, 599-604
24. Yu, Y. M., Wang, L. H., and Tu, S. C. (1987) Pseudomonas cepacia 3-hydroxybenzoate 6-hydroxylase: Stereochemistry, isotope effects, and kinetic mechanism Biochemistry 26, 1105-1110
25. Rajasekharan, S., Rajasekharan, R., and Vaidyanathan, C. S. (1990) Substrate-mediated purification and characterization of a 3-hydroxybenzoic acid-6-hydroxylase from Micrococcus Arch. Biochem. Biophys. 278, 21-25
26. Sumathi, S. and Dasgupta, D. (2006) Interaction of 3-hydroxybenzoate-6- hydroxylase with cibacron blue J. Enzyme Inhib. Med. Chem. 21, 47-53
27. Massey, V. (1991) A simple method for the determination of redox potentials. In Flavins and Flavoproteins (Curti, B., Rochi, S., and Zanetti, G., Eds.) pp 59-66, Water DeGruyter & Co., Berlin.
28. Clark, W. M. (1960) Compilations of data. In Oxidation-Reduction Potentials of Organic Systems, pp 410, Wavery Press, Inc., Baltimore.
29. Clark, W. M. (1960) The standard hydrogen half-cell and the standardization of oxidation-reduction potentials and pH numbers. In Oxidation-Reduction Potentials of Organic Systems, pp 248-272, Wavery Press, Inc., Baltimore.
30. Bernasconi, C. F. (1976) Relaxation time in common multistep systems. In Relaxation Kinetics, pp 40-74, Academic Press, San Diego.
31. Fersht, A. (1999) Measurement and magnitude of enzymatic rate constants. In Enzyme Structure and Mechanism, pp 132-167, W. H. Freeman and Co., NewYork.
32. Eppink, M. H., Schreuder, H. A., and van Berkel, W. J. (1998) Interdomain binding of NADPH in p -hydroxybenzoate hydroxylase as suggested by kinetic, crystallographic and modeling studies of histidine 162 and arginine 269 variants J. Biol. Chem. 273, 21031-21039
33. Strickland, S. and Massey, V. (1973) The mechanism of action of the flavoprotein melilotate hydroxylase J. Biol. Chem. 248, 2953-1962
34. Powlowski, J., Ballou, D., and Massey, V. (1989) A rapid reaction study of anthranilate hydroxylase. Evidence for a catalytically important conformational change during slow initial turnover with anthranilate J. Biol. Chem. 264, 16008-16016
35. Chaiyen, P., Brissette, P., Ballou, D. P., and Massey, V. (1997) Thermodynamics and reduction kinetics properties of 2-methyl-3-hydroxypyridine- 5-carboxylic acid oxygenase Biochemistry 36, 2612-2621
36. Chaiyen, P., Brissette, P., Ballou, D. P., and Massey, V. (1997) Reaction of 2-methyl-3-hydroxypyridine-5-carboxylic acid (MHPC) oxygenase with N-methyl-5-hydroxynicotinic acid: Studies on the mode of binding, and protonation status of the substrate Biochemistry 36, 13856-13864
37. Suske, W. A., van Berkel, W. J., and Kohler, H. P. (1999) Catalytic mechanism of 2-hydroxybiphenyl 3-monooxygenase, a flavoprotein from Pseudomonas azelaica HBP1 J. Biol. Chem. 274, 33355-33365
38. Crozier-Reabe, K. R., Phillips, R. S., and Moran, G. R. (2008) Kynurenine 3-monooxygenase from Pseudomonas fluorescens: Substrate-like inhibitors both stimulate flavin reduction and stabilize the flavin-peroxo intermediate yet result in the production of hydrogen peroxide Biochemistry 47, 12420-12433
39. Arunachalam, U., Massey, V., and Miller, S. M. (1994) Mechanism of p -hydroxyphenylacetate 3-hydroxylase. A two-protein enzyme J. Biol. Chem. 269, 150-155
40. Chaiyen, P., Suadee, C., and Wilairat, P. (2001) A novel two-protein component flavoprotein hydroxylase Eur. J. Biochem. 268, 5550-5561
41. Sucharitakul, J., Chaiyen, P., Entsch, B., and Ballou, D. P. (2005) The reductase of p -hydroxyphenylacetate 3-hydroxylase from Acinetobacter baumannii requires p -hydroxyphenylacetate for effective catalysis Biochemistry 44, 10434-10442
42. Uetz, T., Schneider, R., Snozzi, M., and Egli, T. (1992) Purification and characterization of a two-component monooxygenase that hydroxylates nitrilotriacetate from "Chelatobacter" strain ATCC 29600 J. Bacteriol. 174, 1179-1188
43. Howell, L. G., Spector, T., and Massey, V. (1972) Purification and properties of p -hydroxybenzoate hydroxylase from Pseudomonas fluorescens J. Biol. Chem. 247, 4340-4350
44. Zheng, Y., Wagner, M. A., Jorns, M. S., and Carey, P. R. (2001) Selective enhancement of ligand and flavin Raman modes in charge-transfer complexes of sarcosine oxidase J. Raman Spectrosc. 32, 79-92
45. Tanaka, T., Tamaoki, H., Nishina, Y., Shiga, K., Ohno, T., and Miura, R. (2006) Theoretical study on charge-transfer interaction between acyl-CoA dehydrogenase and 3-thiaacyl-CoA using density functional method J. Biochem. 139, 847-855
46. Prongjit, M., Sucharitakul, J., Wongnate, T., Haltrich, D., and Chaiyen, P. (2009) Kinetic mechanism of pyranose 2-oxidase from Trametes multicolor Biochemistry 48, 4170-4180