Streptomyces coelicolor A3(2) CYP102 protein, a novel fatty acid hydroxylase encoded as a heme domain without an n-terminal redox partner

Applied and Environmental Microbiology

Volumn 76, Issue 6, 2010, Pages 1975-1980

  Lamb, David C ^a   Lei, Li ^b   Zhao, Bin ^b   Yuan, Hang ^b   Jackson, Colin J ^a   Warrilow, Andrew G S ^a   Skaug, Tove ^a   Dyson, Paul J ^b   Dawson, Eric S ^a   Kelly, Steven L ^b   Hachey, David L ^b   Waterman, Michael R ^a,b  

^a SWANSEA UNIVERSITY   (United Kingdom)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARACHIDONIC ACIDS; FERREDOXIN REDUCTASE; FUSION PROTEINS; HEME DOMAIN; HYDROXYLASES; N-TERMINALS; PHYSIOLOGICAL FUNCTIONS; REDOX PARTNERS; S. COELICOLOR; STEREO-SELECTIVE; STREPTOMYCES COELICOLOR A3(2); TRANSPOSON MUTAGENESIS;

ESCHERICHIA COLI; FATTY ACIDS; GENE ENCODING; HEMOGLOBIN; METABOLISM; MUTAGENESIS; PORPHYRINS; PURIFICATION;

ACIDS;

10-HYDROXY-11,12-EPOXYEICOSA-5,8,14-TRIENOIC ACID; 14,15 EPOXY 5,8,11 EICOSATRIENOIC ACID; 14,15-EPOXY-5,8,11-EICOSATRIENOIC ACID; ARACHIDONIC ACID; CYTOCHROME P450; DIHOMO GAMMA LINOLENIC ACID; DRUG DERIVATIVE; FERREDOXIN; FERREDOXIN NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE REDUCTASE; HEPOXILIN B; MIXED FUNCTION OXIDASE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

BACTERIUM; CARBOXYLIC ACID; ENZYME ACTIVITY; GENE EXPRESSION; MUTATION; PHENOTYPE; PROTEIN;

ARTICLE; ENZYME SPECIFICITY; ENZYMOLOGY; ESCHERICHIA COLI; GENE EXPRESSION; GENE EXPRESSION REGULATION; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; MOLECULAR CLONING; STREPTOMYCES COELICOLOR; TRANSPOSON;

8,11,14-EICOSATRIENOIC ACID; ARACHIDONIC ACID; CLONING, MOLECULAR; CYTOCHROME P-450 ENZYME SYSTEM; DNA TRANSPOSABLE ELEMENTS; ESCHERICHIA COLI; FERREDOXIN-NADP REDUCTASE; FERREDOXINS; GENE EXPRESSION; MIXED FUNCTION OXYGENASES; MUTAGENESIS, INSERTIONAL; NADP; STREPTOMYCES COELICOLOR; SUBSTRATE SPECIFICITY;

ESCHERICHIA COLI; SPINACIA OLERACEA; STREPTOMYCES COELICOLOR;

EID: 77749303997     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.03000-09     Document Type: Article

References (26)

1. Bentley, S. D., K. F. Chater, A. M. Cerdeño-Tárraga, G. L. Challis, N. R. Thomson, et al. 2002. Complete genome sequence of the model actinomycete Streptomyces coelicolor A3(2). Nature 417:141-147.
2. Bishop, A., S. Fielding, P. Dyson, and P. Herron. 2004. Systematic mutagenesis of a streptomycete genome: a link between osmoadaptation and antibiotic production. Genome Res. 14:893-900.
3. Doddapaneni, H., R. Chakraborty, and J. S. Yadav. 2005. Genome-wide structural and evolutionary analysis of the P450 monooxygenase genes (P450ome) in the white rot fungus Phanerochaete chrysosporium: evidence for gene duplications and extensive gene clustering. BMC Genomics 6:92.
4. Flett, F., V. Mersinias, and C. P. Smith. 1997. High efficiency intergeneric conjugal transfer of plasmid DNA from Escherichia coli to methyl DNA restricting streptomycetes. FEMS Microbiol. Lett. 155:223-229.
5. Folch, J., M. Lees, and G. H. S. Stanley. 1957. Preparation of lipid extracts from brain tissue. J. Biol. Chem. 226:497-509.
6. Girvan, H. M., T. N. Waltham, R. Neeli, H. F. Collins, K. J. McLean, N. S. Scrutton, D. Leys, and A. W. Munro. 2006. Flavocytochrome P450 BM3 and the origin of CYP102 fusion species. Biochem. Soc. Trans. 34:1173-1177.
7. Glieder, A., E. T. Farinas, and F. H. Arnold. 2002. Laboratory evolution of a soluble, self-sufficient, highly active alkane hydroxylase. Nat. Biotechnol. 20:1135-1139.
8. Graham-Lorence, S., G. Truan, J. A. Peterson, J. R. Falck, S. Wei, C. Helvig, and J. H. Capdevila. 1997. An active site substitution, F87V, converts cytochrome P450 BM-3 into a regio- and stereoselective (14S,15R)-arachidonic acid epoxygenase. J. Biol. Chem. 272:1127-1135.
9. Gustafsson, M. C., C. N. Palmer, C. R. Wolf, and C. von Wachenfeldt. 2001. Fatty-acid-displaced transcriptional repressor, a conserved regulator of cytochrome P450 102 transcription in Bacillus species. Arch. Microbiol. 176: 459-464.
10. Gustafsson, M. C., O. Roitel, K. R. Marshall, M. A. Noble, S. K. Chapman, A. Pessegueiro, A. J. Fulco, M. R. Cheesman, C. von Wachenfeldt, and A. W. Munro. 2004. Expression, purification, and characterization of Bacillus subtilis cytochromes P450 CYP102A2 and CYP102A3: flavocytochrome homologues of P450 BM3 from Bacillus megaterium. Biochemistry 43:5474-5487.
11. Kagawa N., H. Hori, M. R. Waterman, and S. Yoshioka. 2004. Characterization of stable human aromatase expressed in E. coli. Steroids 69:235-243.
12. Kieser, T., M. J. Bibb, M. J. Buttner, K. F. Chater, and D. A. Hopwood. 2000. Practical Streptomyces genetics. The John Innes Foundation, Norwich, United Kingdom.
13. Kitazume, T., N. Takaya, N. Nakayama, and H. Shoun. 2000. Fusarium oxysporum fatty-acid subterminal hydroxylase (CYP505) is a membrane-bound eukaryotic counterpart of Bacillus megaterium cytochrome P450BM3. J. Biol. Chem. 275:39734-39740.
14. Lamb, D. C., T. Skaug, H.-L. Song, C. J. Jackson, L. Podust, M. R. Waterman, D. B. Kell, D. E. Kelly, and S. L. Kelly. 2002. The cytochrome P450 complement (CYPome) of Streptomyces coelicolor A3(2). J. Biol. Chem. 277:24000-24005.
15. Lamb, D. C., H. Ikeda, D. R. Nelson, J. Ishikawa, T. Skaug, C. J. Jackson, S. Omura, M. R. Waterman, and S. L. Kelly. 2002. Cytochrome P450 complement (CYPome) of the avermectin-producer Streptomyces avermitilis and comparison to that of Streptomyces coelicolor A3(2). Biochem. Biophys. Res. Commun. 307:610-619.
16. Narhi, L. O., and A. J. Fulco. 1986. Characterization of a catalytically self-sufficient 119,000-Dalton cytochrome P-450 monooxygenase induced by barbiturates in Bacillus megaterium. J. Biol. Chem. 261:7160-7169.
17. Narhi, L. O., and A. J. Fulco. 1987. Identification and characterization of two functional domains in cytochrome P-450BM-3, a catalytically self-sufficient monooxygenase induced by barbiturates in Bacillus megaterium. J. Biol. Chem. 262:6683-6690.
18. Noble, M. A., C. S. Miles, S. K. Chapman, D. A. Lysek, A. C. MacKay, G. A. Reid, R. P. Hanzlik, and A. W. Munro. 1999. Roles of key active-site residues in flavocytochrome P450 BM3. Biochem. J. 339:371-379.
19. Omura, T., and R. Sato. 1964. The carbon monoxide binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem. 239:2379-2385.
20. Rupasinghe, S., M. A. Schuler, N. Kagawa, H. Yuan, L. Lei, B. Zhao, S. L. Kelly, M. R. Waterman, and D. C. Lamb. 2006. The cytochrome P450 gene family CYP157 does not contain EXXR in the K-helix reducing the absolute conserved P450 residues to a single cysteine. FEBS Lett. 280:6338-6342.
21. Ryding, N. J., G. H. Kelemen, C. A. Whatling, K. Flardh, M. J. Buttner, and K. F. Chater. 1998. A developmentally regulated gene encoding a repressorlike protein is essential for sporulation in Streptomyces coelicolor A3(2). Mol. Microbiol. 29:343-357.
22. Urlacher, V., and R. D. Schmid. 2002. Biotransformations using prokaryotic P450 monooxygenases. Curr. Opin. Biotechnol. 13:557-564.
23. Van Vugt-Lussenburg, B. M., M. C. Damsten, D. M. Maasdijk, N. P. Vermeulen, and J. N. Commandeur. 2006. Heterotropic and homotropic cooperativity by a drug-metabolising mutant of cytochrome P450 BM3. Biochem. Biophys. Res. Commun. 346:810-818.
24. Zhao, B., F. P. Guengerich, A. Bellamine, D. C. Lamb, M. Izumikawa, L. Lei, L. M. Podust, M. Sundaramoorthy, J. A. Kalaitzis, L. M. Reddy, S. L. Kelly, B. S. Moore, D. Stec, M. Voehler, J. R. Falck, T. Shimada, and M. R. Waterman. 2005. Binding of two flaviolin substrate molecules, oxidative coupling, and crystal structure of Streptomyces coelicolor A3(2) cytochrome P450 158A2. J. Biol. Chem. 280:11599-11607.
25. Zhao, B., and M. R. Waterman. 2007. Novel properties of P450s in Streptomyces coelicolor. Drug Metab. Rev. 39:343-352.
26. Zhao, B., X. Lin, L. Lei, D. C. Lamb, S. L. Kelly, M. R. Waterman, and D. E. Cane. 2008. Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2). J. Biol. Chem. 283:8183-8189.