Mechanism of the severe inhibition of tetrachlorohydroquinone dehalogenase by its aromatic substrates

Biochemistry

Volumn 46, Issue 14, 2007, Pages 4438-4447

  Warner, Joseph R ^a   Copley, Shelley D ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLUTATHIONE; PENTACHLOROPHENOL; TETRACHLOROHYDROQUINONE (TCHQ) DEHALOGENASE; THIOL-DISULFIDE EXCHANGE REACTION;

BINDING SITES; CATALYST ACTIVITY; DEGRADATION; DEHALOGENATION; MONOMERS; REACTION KINETICS; SUBSTRATES;

ENZYME INHIBITION;

AROMATIC COMPOUND; BACTERIAL ENZYME; DISULFIDE; GLUTATHIONE; GLUTATHIONE TRANSFERASE; TETRACHLOROHYDROQUINONE; TETRACHLOROHYDROQUINONE DEHALOGENASE; THIOL; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; ENZYME BINDING; ENZYME INHIBITION; ENZYME SUBSTRATE; NONHUMAN; PRIORITY JOURNAL; PROTEIN FAMILY; SOIL MICROFLORA; SPHINGOBIUM CHLOROPHENOLICUM;

BINDING SITES; BUFFERS; CATALYSIS; DOSE-RESPONSE RELATIONSHIP, DRUG; GLUTATHIONE; GLUTATHIONE DISULFIDE; HYDROGEN-ION CONCENTRATION; HYDROLASES; KINETICS; MODELS, BIOLOGICAL; PROTEIN BINDING; SPECTROPHOTOMETRY, ULTRAVIOLET; SUBSTRATE SPECIFICITY;

SPHINGOBIUM CHLOROPHENOLICUM;

EID: 34147126962     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi0620104     Document Type: Article

References (15)

1. Cline, R. E., Hill, R. H., Phillips, D. L., and Needham, L. L. (1989) Pentachlorophenol measurements in body fluids of people in log homes and workplaces, Arch. Environ. Contam. Toxicol. 18, 475-481.
2. Copley, S. D. (2000) Evolution of a metabolic pathway for degradation of a toxic xenobiotic: the patchwork approach, Trends Biochem. Sci. 25, 261-265.
3. Walsh, T. A., and Ballou, D. P. (1983) Halogenated protocatechuates as substrates for protocatechuate dioxygenase from Pseudomonas cepacia, J. Biol. Chem. 258, 14413-14421.
4. Dorn, E., and Knackmuss, H.-J. (1978) Chemical structure and biodegradability of halogenated aromatic compounds: Substituent effects on 1,2-dioxygenation of catechol, Biochem. J. 174, 85-94.
5. Broderick, J. B., and O'Halloran, T. V. (1991) Overproduction, purification, and characterization of chlorocatechol dioxygenase, a non-heme iron dioxygenase with broad substrate tolerance, Biochemistry 30, 7349-7358.
6. Xu, L., Lawson, S. L., Resing, K., Babbitt, P. C., and Copley, S. D. (1999) Evidence that pcpA encodes 2,6- dichlorohydroquinone dioxygenase, the ring-cleavage enzyme required for pentachlorophenol degradation in Sphingomonas chlorophenolica Strain ATCC 39723, Biochemistry 38, 7659-7669.
7. Anandarajah, K., Kiefer, P. M., and Copley, S. D. (2000) Recruitment of a double bond isomerase to serve as a reductive dehalogenase during biodegradation of pentachlorophenol, Biochemistry 39, 5303-5311.
8. McCarthy, D. L., Louie, D. F., and Copley, S. D. (1997) Identification of a covalent intermediate between glutathione and Cysteine 13 during catalysis by tetrachlorohydroquinone dehalogenase, J. Am. Chem. Soc. 119, 11337-11338.
9. Kiefer, P. M., Jr., and Copley, S. D. (2002) Characterization of the initial steps in the reductive dehalogenation catalyzed by tetrachlorohydroquinone dehalogenase, Biochemistry 41, 1315-1322.
10. Kiefer, P. M., Jr., McCarthy, D. L., and Copley, S. D. (2002) The reaction catalyzed by tetrachlorohydroquinone dehalogenase does not involve nucleophilic aromatic substitution, Biochemistry 41, 1308-1314.
11. Warner, J. P., Lawson, S. L., and Copley, S. D. (2005) A mechanistic investigation of the thiol-disulfide exchange step in the reductive dehalogenation catalyzed by tetrachlorohydroquinone dehalogenase, Biochemistry 44, 10360-10368.
12. McCarthy, D. L., Navarrete, S., Willett, W. S., Babbitt, P. C., and Copley, S. D. (1996) Exploration of the relationship between tetrachlorohydroquinone dehalogenase and the glutathione S-transferase superfamily, Biochemistry 35, 14634-14642.
13. Ellman, G. (1959) A colorimetric method for determining low concentrations of mercaptans, Arch. Biochem. Biophys. 82, 70-77.
14. Segel, I. H. (1975) Enzyme kinetics: behavior and analysis of rapid equilibrium and steady-state enzyme systems, John Wiley & Sons, Inc., New York.
15. McCarthy, D. L., Claude, A., and Copley, S. D. (1997) In vivo levels of chlorinated hydroquinones in a pentachlorophenol-degrading bacterium, Appl. Environ. Microbiol. 63, 1883-1888.