Diverse mechanistic approaches to difficult chemical transformations: Microbial dehalogenation of chlorinated aromatic compounds

Chemistry and Biology

Volumn 4, Issue 3, 1997, Pages 169-174

  Copley, Shelley D ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031105253     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(97)90285-4     Document Type: Short Survey

References (27)

1. Brown, J.F., Bedard, D.L., Brennan, M.J., Carnahan, J.C., Feng, H. & Wagner, R.E. (1987). Polychlorinated biphenyl dechlorination in aquatic sediments. Science 236, 709-712.
2. Yang, G., Liang, P.-H. & Dunaway-Mariano, D. (1994). Evidence for nucleophilic catalysis in the aromatic substitution reaction catalyzed by (4-chlorobenzoyl)coenzyme A dehalogenase. Biochemistry 33, 8527-8531.
3. Crooks, G.P., Xu, L., Barkley, R.M. & Copley, S.D. (1995). Exploration of possible mechanisms for 4-chlorobenzoyl CoA dehalogenase: evidence for an aryl-enzyme intermediate. J. Am. Chem. Soc. 117, 10791-10798.
4. Benning, M.M., et al., & Holden, H.M. (1996). Structure of 4-chlorobenzoyl coenzyme A dehalogenase determined to 1.8 Å resolution: an enzyme catalyst generated via adaptive mutation. Biochemistry 35, 8103-8109.
5. 13C-NMR spectral studies of dehalogenase complexes of benzoyl-CoA adducts. Biochemistry 34, 13881-13888.
6. D'Ordine, R.L., Tonge, P.J., Carey, P.R. & Anderson, V.E. (1994). Electronic rearrangement induced by substrate analog binding to the enoyl-CoA hydratase active site: evidence for substrate activation. Biochemistry 33, 12635-1 2643.
7. Engel, C.K., Mathieu, M., Zeelen, J.P., Hiltunen, J.K. & Wierenga, R.K. (1996). Crystal structure of enoyl-coenzyme A (CoA) hydratase at 2.5 Å resolution: a spiral fold defines the CoA-binding pocket. EMBO J. 15, 5135-5145.
8. Lacourciere, G.M. & Armstrong, R.N. (1993). The catalytic mechanism of microsomal epoxide hydrolase involves an ester intermediate. J. Am. Chem. Soc. 115, 10466-10467.
9. Verschueren, K.H.G., Seljee, F., Rozeboom, H.J., Kalk, K.H. & Dijkstra, B.W. (1993). Crystallographic analysis of the catalytic mechanism of haloalkane dehalogenase. Nature 363, 693-698.
10. Pries, F., et al., & Janssen, D.B. (1994). Site-directed mutagenesis and oxygen isotope incorporation studies of the nucleophilic aspartate of haloalkane dehalogenase. Biochemistry 33, 1242-1247.
11. Lee, J.-Y. & Xun, L (1997). Purification and characterization of 2,6-dichloro-p-hydroquinone chlorohydrolase from Flavobacterium sp. strain ATCC 39723. J. Bacteriol., in press.
12. De Souza, M.L., Sadowsky, M.J. & Wackett, L.P. (1996). Atrazine chlorohydrolase from Pseudomonas sp. strain ADP: gene sequence, enzyme purification, and protein characterization. J. Bacteriol. 178, 4894-4900.
13. Mulbry, W.W. (1994). Purification and characterization of an inducible s-triazine hydrolase from Rhodococcus corallinus NRRL B-15444R. Appl. Env. Microbiol. 60, 613-618.
14. Ni, S., Fredrickson, J.K. & Xun, L. (1995). Purification and characterization of a novel 3-chlorobenzoate reductive dehalogenase from the cytoplasmic membrane of Desulfomonile tiedjei DCB-1. J. Bacteriol. 177, 5135-5139.
15. McCarthy, D.L., Navarrete, S., Willett, W.S., Babbitt, P.C. & Copley, S.D. (1996). Exploration of the relationship between tetrachlorohydroquinone dehalogenase and the glutathione S-transferase superfamily. Biochemistry 35, 14634-14642.
16. Romanov, V. & Hausinger, R.P. (1996). NADPH-dependent reductive ortho dehalogenation of 2,4-dichlorobenzoic acid in Corynebacterium sepedonicum KZ-4 and Coryneform bacterium strain NTB-1 via 2,4-dichlorobenzoyl coenzyme A. J. Bacteriol. 178, 2656-2661.
17. Ni, S., Fredrickson, J.K. & Xun, L. (1995). Purification and characterization of a novel 3-chlorobenzoate reductive dehalogenase from the cytoplasmic membrane of Desulfomonile tiedjei DCB-1. J. Bacteriol. 177, 5135-5139.
18. Markus, A., Klages, U., Krauss, S. & Lingens, F. (1984). Oxidation and dehalogenation of 4-chlorophenylacetate by a two-component enzyme system from Pseudomonas sp. strain CBS3. J. Bacteriol. 160, 618-621.
19. Fetzner, S., Müller, R. & Lingens, F. (1992). Purification and some properties of 2-halobenzoate 1,2-dioxygenase, a two-component enzyme system from Pseudomonas cepacia 2CBS. J. Bacteriol. 174, 279-290.
20. Romanov, V. & Hausinger, R.P. (1994). Pseudomonas aeruginosa 142 uses a three-component ortho-halobenzoate 1,2-dioxygenase for metabolism of 2,4-dichloro- and 2-chlorobenzoate. J. Bacteriol. 176, 3368-3374.
21. Mason, J.R. & Cammack, R. (1992). The electron-transport proteins of hydroxylating bacterial dioxygenases. Ann. Rev. Microbiol. 46 277-305.
22. Pavel, E.G., Martins, L.J., Ellis, W.R., Jr & Solomon, E.I. (1994). Magnetic circular dichroism studies of exogenous ligand and substrate binding to the non-heme ferrous active site in phthalate dioxygenase. Chem. Biol. 1, 173-183.
23. Xun, L. & Orser, C.S. (1991). Purification and properties of pentachlorophenol hydroxylase, a flavoprotein from Flavobacterium sp. strain ATCC 39723. J. Bacteriol. 173, 4447-4453.
24. Orser, C., Lange, C.C., Xun, L., Zahrt, T.C., Schneider, B.J. (1993). Cloning, sequence analysis, and expression of the Flavobacterium pentachlorophenol-4-monooxygenase gene in Escherichia coli. J. Bacteriol. 175, 411-416.
25. Husain, M., Entsch, B., Ballou, D.P., Massey, V. & Chapman, P.J. (1980). Fluoride elimination from substrates in hydroxylation reactions catalyzed by p-hydroxybenzoate hydroxylase. J. Biol. Chem. 255, 4189-4197.
26. Xun, L., Topp, E. & Orser, C. (1992). Diverse substrate range of a Flavobacterium pentachlorophenol hydroxylase and reaction stoichiometries. J. Bacteriol. 174, 2898-2902.
27. Uotila, J.S., Kitunen, V.H., Saastamoinen, T., Coote, T., Häggblom, M.M. & Salkinoja-Salonen, M.S. (1992). Characterization of aromatic dehalogenases of Mycobacterium fortuitum CG-2. J. Bacteriol. 174, 5669-5675.