A novel class of self-sufficient cytochrome P450 monooxygenases in prokaryotes

Trends in Microbiology

Volumn 10, Issue 11, 2002, Pages 502-508

  De Mot, René ^a   Parret, Annabel H A ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; ENZYME; HYBRID PROTEIN; OXIDOREDUCTASE; POLYPEPTIDE; UNSPECIFIC MONOOXYGENASE;

ACTINOBACTERIA; BACILLUS; BACILLUS ANTHRACIS; BACILLUS CEREUS; BACTERIAL STRAIN; BURKHOLDERIA; ELECTRON TRANSPORT; ENZYME ANALYSIS; FUNGUS; GENOME ANALYSIS; MICROSOME; NONHUMAN; PATHOGENICITY; PRIORITY JOURNAL; PROKARYOTE; PROTEIN DOMAIN; PROTEIN FAMILY; RALSTONIA; RALSTONIA METALLIDURANS; REVIEW; RHODOCOCCUS; SEQUENCE HOMOLOGY;

CYTOCHROME P-450 ENZYME SYSTEM; ELECTRON TRANSPORT; MODELS, GENETIC; MODELS, MOLECULAR; OXIDOREDUCTASES; PHYLOGENY; PROKARYOTIC CELLS; PROTEIN STRUCTURE, TERTIARY;

ACTINOBACTERIA (CLASS); BACILLUS ANTHRACIS; BACILLUS CEREUS; BACTERIA (MICROORGANISMS); BURKHOLDERIA; FUNGI; PROKARYOTA; RALSTONIA; RHODOCOCCUS; RHODOCOCCUS ERYTHROPOLIS; WAUTERSIA METALLIDURANS;

EID: 0036844477     PISSN: 0966842X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0966-842X(02)02458-7     Document Type: Review

References (50)

1. Tijet N., et al. The cytochrome P450 gene superfamily in Drosophila melanogaster: annotation, intron-exon organization and phylogeny. Gene. 262:2001;189-198.
2. Lamb D.C., et al. The cytochrome P450 complement (CYPome) of Streptomyces coelicolor A3(2). J. Biol. Chem. 277:2002;24000-24005.
3. Anzenbacher P., Anzenbacherova E. Cytochromes P450 and metabolism of xenobiotics. Cell. Mol. Life Sci. 58:2001;737-747.
4. Domanski T.L., Halpert J.R. Analysis of mammalian cytochrome P450 structure and function by site-directed mutagenesis. Curr. Drug Metab. 2:2001;117-137.
5. Scott J.G., Wen Z. Cytochromes P450 of insects: the tip of the iceberg. Pest Manag. Sci. 57:2001;958-967.
6. Schuler M.A., et al. Plant cytochrome P450 monooxygenases. Crit. Rev. Plant Sci. 15:1996;235-284.
7. Lupetti A., et al. Molecular basis of resistance to azole antifungals. Trends Mol. Med. 8:2002;76-81.
8. Guardiola-Diaz H.M., et al. Azole-antifungal binding to a novel cytochrome P450 from Mycobacterium tuberculosis: implications for treatment of tuberculosis. Biochem. Pharmacol. 61:2001;1463-1470.
9. Andersen J.F., et al. Substrate specificity of 6-deoxyerythronolide B hydroxylase, a bacterial cytochrome P450 of erythromycin A biosynthesis. Biochemistry. 32:1993;1905-1913.
10. Ikeda H., et al. Organization of the biosynthetic gene cluster for the polyketide anthelmintic macrolide avermectin in Streptomyces avermitilis. Proc. Natl. Acad. Sci. U. S. A. 96:1999;9509-9514.
11. Tang L., et al. Cloning and heterologous expression of the epothilone gene cluster. Science. 287:2000;640-642.
12. Healy F.G., et al. Involvement of a cytochrome P450 monooxygenase in thaxtomin A biosynthesis by Streptomyces acidiscabies. J. Bacteriol. 184:2002;2019-2029.
13. terp. Isolation and purification of the protein and cloning and sequencing of its operon. J. Biol. Chem. 267:1992;14193-14203.
14. Patel N.V., Omer C.A. Phenobarbital and sulfonylurea-inducible operons encoding herbicide-metabolizing cytochromes P-450 in Streptomyces griseolus. Gene. 112:1992;67-76.
15. Nagy I., et al. Degradation of the thiocarbamate herbicide EPTC (S-ethyl dipropylcarbamothioate) and biosafening by Rhodococcus sp. strain NI86/21 involve an inducible cytochrome P-450 system and aldehyde dehydrogenase. J. Bacteriol. 177:1995;676-687.
16. Chavaux S., et al. Cloning of a genetically unstable cytochrome P-450 gene cluster involved in degradation of the pollutant ethyl tert-butyl ether by Rhodococcus ruber. J. Bacteriol. 183:2001;6551-6557.
17. Chen X., et al. Crystal structure of the F87W/Y96F/V247L mutant of cytochrome P450cam with 1,3,5-trichlorobenzene bound and further protein engineering for the oxidation of pentachlorobenzene and hexachlorobenzene. J. Biol. Chem. 277:2002;37519-37526.
18. Kellner D.G., et al. Engineering cytochrome P450s for bioremediation. Curr. Opin. Biotechnol. 8:1997;274-278.
19. Degtyarenko K.N., Kulikova T.A. Evolution of bioinorganic motifs in P450-containing systems. Biochem. Soc. Trans. 29:2001;139-147.
20. Narhi L.O., Fulco A.J. Characterization of a catalytically self-sufficient 119,000-dalton cytochrome P-450 monooxygenase induced by barbiturates in Bacillus megaterium. J. Biol. Chem. 261:1986;7160-7169.
21. Munro A.W., et al. P450 BM3: the very model of a modern flavocytochrome. Trends Biochem. Sci. 27:2002;250-257.
22. Guengerich F.P., Parikh A. Expression of drug-metabolizing enzymes. Curr. Opin. Biotechnol. 8:1997;623-628.
23. Nakayama N., et al. Cytochrome P450foxy, a catalytically self-sufficient fatty acid hydroxylase of the fungus Fusarium oxysporum. J. Biochem. 119:1996;435-440.
24. Kitazume T., et al. Fusarium oxysporum fatty-acid subterminal hydroxylase (CYP505) is a membrane-bound eukaryotic counterpart of Bacillus megaterium cytochrome P450 BM3. J. Biol. Chem. 275:2000;39734-39740.
25. Kunst F., et al. The complete genome sequence of the Gram-positive bacterium Bacillus subtilis. Nature. 390:1997;249-256.
26. Seo J.A., et al. Characterization of four clustered and coregulated genes associated with fumonisin biosynthesis in Fusarium verticillioides. Fungal Genet. Biol. 34:2001;155-165.
27. Yu T-W., et al. The biosynthetic gene cluster of the maytansinoid antitumor agent ansamitocin from Actinosynnema pretiosum. Proc. Natl. Acad. Sci. U. S. A. 99:2002;7968-7973.
28. Roberts G.A., et al. Identification of a new class of cytochrome P450 from a Rhodococcus sp. J. Bacteriol. 184:2002;3898-3908.
29. Jenkins C.M., Waterman M.R. NADPH-flavodoxin reductase and flavodoxin from Escherichia coli: characteristics as a soluble microsomal P450 reductase. Biochemistry. 37:1998;6106-6113.
30. cin (CYP176A), isolation, expression, and chracterization. J. Biol. Chem. 277:2002;27725-27732.
31. Gibson D.T., Parales R.E. Aromatic hydrocarbon dioxygenases in environmental biotechnology. Curr. Opin. Biotechnol. 11:2000;236-243.
32. Gassner G.T., et al. Structure and mechanism of the iron-sulfur flavoprotein phthalate dioxygenase reductase. FASEB J. 9:1995;1411-1418.
33. Nelson D.R. Cytochrome P450 and the individuality of species. Arch. Biochem. Biophys. 369:1999;1-10.
34. Denis-Larose C., et al. Characterization of the basic replicon of Rhodococcus plasmid pSOX and development of a Rhodococcus-Escherichia coli shuttle vector. Appl. Environ. Microbiol. 64:1998;4363-4367.
35. Wang M., et al. Three-dimensional structure of NADPH-cytochrome P450 reductase: prototype for FMN- and FAD-containing enzymes. Proc. Natl. Acad. Sci. U. S. A. 94:1997;8411-8416.
36. cam triple fusion protein. Construction of a self-sufficient Escherichia coli catalytic system. J. Biol. Chem. 271:1996;22462-22469.
37. Cao P.R., et al. Construction and characterization of a catalytic fusion protein system: P-450(11()-adrenodoxin reductase-adrenodoxin. Biochim. Biophys. Acta. 1476:2000;253-264.
38. Koga H., et al. Cloning and nucleotide sequences of NADH-putidaredoxin reductase gene (camA) and putidaredoxin gene (camB) involved in cytochrome P-450cam hydroxylase of Pseudomonas putida. J. Biochem. 106:1989;831-836.
39. Brakmann S. Discovery of superior enzymes by directed molecular evolution. Chembiochem. 2:2001;865-871.
40. Li Q-S., et al. Engineering cytochrome P450 BM-3 for oxidation of polycyclic aromatic hydrocarbons. Appl. Environ. Microbiol. 67:2001;5735-5739.
41. Appel D., et al. A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes. J. Biotechnol. 88:2001;167-171.
42. Zhi L., et al. Oxidative biotransformations using oxygenases. Curr. Opin. Chem. Biol. 6:2002;136-144.
43. Dixon R.A., Steele C.L. Flavanoids and isoflavanoids - a gold mine for metabolic engineering. Trends Plant Sci. 4:1999;394-400.
44. Rushmore T.H., et al. Bioreactor systems in drug metabolism: synthesis of cytochrome P450-generated metabolites. Metab. Eng. 2:2000;115-125.
45. Xue Y., Sherman D.H. Biosynthesis and combinatorial biosynthesis of pikromycin-related macrolides in Streptomyces venezuelae. Metab. Eng. 3:2001;15-26.
46. Guengerich F.P. Cytochrome P450 enzymes in the generation of commercial products. Nat. Rev. Drug Discov. 1:2002;359-366.
47. Werck-Reichhart D., et al. Cytochromes P450 for engineering herbicide tolerance. Trends Plant Sci. 5:2000;116-123.
48. Wittstock U., Halkier B.A. Glucosinolate research in the Arabidopsis era. Trends Plant Sci. 7:2002;263-270.
49. Martz E. Protein Explorer: easy yet powerful macromolecular visualization. Trends Biochem. Sci. 27:2002;107-109.
50. Van de Peer Y., De Wachter R. TREECON for Windows: a software package for the construction and drawing of evolutionary trees for the Microsoft Windows environment. Comput. Appl. Biosci. 10:1994;569-570.