Engineering Cytochrome P450 BM-3 for Oxidation of Polycyclic Aromatic Hydrocarbons

Applied and Environmental Microbiology

Volumn 67, Issue 12, 2001, Pages 5735-5739

  Li, Qing Shan ^a   Ogawa, Jun ^a   Schmid, Rolf D ^b   Shimizu, Sakayu ^a  

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P 450 ENZYME SYSTEM; CYTOCHROME P450; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; BACILLUS MEGATERIUM; BIODEGRADATION; ENZYMOLOGY; ESCHERICHIA COLI; GENETIC ENGINEERING; GENETICS; METABOLISM; MUTATION; OXIDATION REDUCTION REACTION;

BACILLUS MEGATERIUM; BIODEGRADATION; CYTOCHROME P-450 ENZYME SYSTEM; ESCHERICHIA COLI; GENETIC ENGINEERING; MUTATION; OXIDATION-REDUCTION; POLYCYCLIC HYDROCARBONS, AROMATIC; SUPPORT, NON-U.S. GOV'T;

EID: 0035653258     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/AEM.67.12.5735-5739.2001     Document Type: Article

References (23)

1. Boddupalli, S. S., R. W. Estabrook, and J. A. Peterson. 1990. Fatty acid monooxygenation by cytochrome P450BM-3. J. Biol. Chem. 265:4233-4239.
2. Carmichael, A. B., and L.-L. Wong. 2001. Protein engineering of Bacillus megaterium CYP102: the oxidation of polycyclic aromatic hydrocarbons. Eur. J. Biochem. 268:3117-3125.
3. Cerniglia, C. E. 1992. Biodegradation of PAHs. Biodegradation 3:351-368.
4. Graham-Lorence, S. E., G. Truan, J. A. Peterson, J. R. Falck, S. Wei, C. Helvig, and J. H. Capdevila. 1997. An active site substitution. F87V, converts cytochrome P450BM-3 into a regio- and stereoselective (14S, 15R)-arachidonic acid epoxygenase. J. Biol. Chem. 272:1127-1135.
5. Guengerich, F. P. 1991. Reactions and significance of cytochrome P-450 enzymes. J. Biol. Chem. 266:10019-10022.
6. Harford-Cross, C. F., A. B. Carmichael, F. K. Allan, P. A. England, D. A. Rouch, and L.-L. Wong. 2000. Protein engineering of cytochrome P450cam (CYP101) for the oxidation of polycyclic aromatic hydrocarbons. Protein Eng. 13:121-128.
7. Johnson, A. C., P. F. Larsen, D. F. Gadbois, and A. W. Houmason. 1985. The distribution of polycyclic aromatic hydrocarbons in the surficial sediments of Penobscot Bay (Maine, USA) in relation to possible sources and to other sites worldwide. Mar. Environ. Res. 15:1-16.
8. Joo, H., Z. Lin, and F. H. Arnold. 1999. Laboratory evolution of peroxide-mediated cytochrome P450 hydroxylation. Nature 339: 670-673.
9. Li, H., and T. L. Poulos. 1997. The structure of the cytochrome p450BM-3 haem domain complexed with the fatty acid structure, palmitoleic acid. Nat. Struct. Biol. 4:140-146.
10. Li, H., and T. L. Poulos. 1999. Fatty acid metabolism, conformational change, and electron transfer in cytochrome P-450(BM-3). Biochim. Biophys. Acta 1441:141-149.
11. Li, Q. S., U. Schwaneberg, F. Fischer, and R. D. Schmid. 2000. Directed evolution of the fatty acid hydroxylase P450BM-3 into an indole-hydroxylating catalyst. Chem. Eur. J. 6:1531-1535.
12. Li, Q. S., U. Schwaneberg, M. Fischer, J. Schmitt, J. Pleiss, S. Lutz-Wahl, and R. D. Schmid. 2001. Rational evolution of a medium chain-specific cytochrome P450 BM-3 variant. Biochim. Biophys. Acta 1545:114-121.
13. 2 inactivation of cytochrome P450 BM-3. Biochem. Biophys. Res. Commun. 280:1258-1261.
14. Loewen, P. C., B. L. Triggs, C. S. George, and B. E. Hrabarchuk. 1985. Genetic mapping of katG, a locus that affects synthesis of the bifunctional catalase-peroxidase hydroperoxidase I in Escherichia coli. J. Bacteriol. 162: 661-667.
15. Mansuy, D. 1998. The great diversity of reactions catalyzed by cytochromes P450. Comp. Biochem. Physiol. C 121:5-14.
16. Miles, C. S., T. W. B. Ost, M. A. Noble, A. W. Munro, and S. K. Chapman. 2000. Protein engineering of cytochromes P450. Biochim. Biophys. Acta 1543:383-407.
17. Narhi, L. O., and A. J. Fulco. 1986. Characterization of a catalytically self-sufficient 119,000-Dalton cytochrome P450 monoxygenase induced by barbiturates in Bacillus megaterium. J. Biol. Chem. 261:7160-7169.
18. Ortiz de Montellano, P. R. (ed.). 1995. Cytochrome P450: structure, mechanism and biochemistry, 2nd ed. Plenum Press, New York, N.Y.
19. Ost, T. W. B., C. S. Miles, J. Murdoch, Y.-F. Cheung, G. A. Reid, S. K. Chapman, and A. W. Munro. 2000. Rational redesign of the substrate binding site of flavocytochrome P450 BM-3. FEBS Lett. 486:173-177.
20. Ruettinger, R. T., L. P. Wen, and A. J. Fulco. 1989. Coding nucleotide, 5′ regulatory, and deduced amino acid sequences of P-450BM-3, a single peptide cytochrome P-450: NADPH-P-450 reductase from Bacillus megaterium. J. Biol. Chem. 264:10987-10995.
21. Shou, M., F. J. Gonzalez, and H. V. Gelboin. 1996. Stereoselective epoxidation and hydration at the K-region of polycyclic aromatic hydrocarbons by cDNA-expressed cytochromes P450 1A1, 1A2, and epoxide hydrolase. Biochemistry 35:15807-15813.
22. Sono, M., M. R. Roach, E. D. Coulter, and J. H. Dawson. 1996. Hemecontaining oxygenases. Chem. Rev. 96:2841-2887.
23. Truan, G., and J. A. Peterson. 1998. Thr268 in substrate binding and catalysis in P4350 BM-3. Arch. Biochem. Biophys. 349:53-64.