Sites of covalent attachment of CYP4 enzymes to heme: Evidence for microheterogeneity of P450 heme orientation

Biochemistry

Volumn 44, Issue 42, 2005, Pages 13914-13920

  Baer, Brian R ^a   Schuman, Jason T ^a   Campbell, A Patricia ^a   Cheesman, Matthew J ^a   Nakano, Mariko ^a   Moguilevsky, Nicole ^b   Kunze, Kent L ^a   Rettie, Allan E ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CELLS; CHROMATOGRAPHY; ESCHERICHIA COLI; HYDROPHOBICITY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE;

CYP4 ENZYMES; HEME; HYDROPHOBIC INTERACTIONS;

ENZYMES;

CARBOXYLIC ACID DERIVATIVE; CYSTEINE; CYTOCHROME P450; CYTOCHROME P450 4B1; ESTER; GLUTAMIC ACID; HEME; IRON; LIGAND; METHYL GROUP; PROPIONIC ACID DERIVATIVE; RECOMBINANT ENZYME; RECOMBINANT PROTEIN; THIOL DERIVATIVE;

ARTICLE; BINDING SITE; CHROMATOGRAPHY; COVALENT BOND; ESCHERICHIA COLI; HYDROPHOBICITY; INSECT CELL; MASS SPECTROMETRY; MOLECULAR INTERACTION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTEIN PROTEIN INTERACTION;

ARYL HYDROCARBON HYDROXYLASES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HEME; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

ESCHERICHIA COLI; INSECTA;

EID: 27144469263     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi051267j     Document Type: Article

References (29)

1. Guengerich, F. P. (2001) Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity, Chem. Res. Toxicol. 14, 611-650.
2. Williams, P. A., Cosme, J., Ward, A., Angove, H. C., Matak Vinkovic, D., and Jhoti, H. (2003) Crystal structure of human cytochrome P450 2C9 with bound warfarin, Nature 424, 464-468.
3. Hoch, U., and Ortiz De Montellano, P. R. (2001) Covalently linked heme in cytochrome P4504A fatty acid hydroxylases, J. Biol. Chem. 276, 11339-11346.
4. Henne, K. R., Kunze, K. L., Zheng, Y. M., Christmas, P., Soberman, R. J., and Rettie, A. E. (2001) Covalent linkage of prosthetic heme to CYP4 family P450 enzymes, Biochemistry 40, 12925-12931.
5. Lebrun, L. A., Xu, F., Kroetz, D. L., and Ortiz De Montellano, P. R. (2002) Covalent attachment of the heme prosthetic group in the CYP4F cytochrome P450 family, Biochemistry 41, 5931-5937.
6. Lebrun, L. A., Hoch, U., and Ortiz De Montellano, P. R. (2002) Autocatalytic mechanism and consequences of covalent heme attachment in the cytochrome P4504A family, J. Biol. Chem. 277, 12755-12761.
7. Zheng, Y. M., Baer, B. R., Kneller, M. B., Henne, K. R., Kunze, K. L., and Rettie, A. E. (2003) Covalent heme binding to CYP4B1 via Glu310 and a carbocation porphyrin intermediate, Biochemistry 42, 4601-4606.
8. Fiedler, T. J., Davey, C. A., and Fenna, R. E. (2000) X-ray crystal structure and characterization of halide-binding sites of human myeloperoxidase at 1.8 Å resolution, J. Biol. Chem. 275, 11964-11971.
9. Rae, T. D., and Goff, H. M. (1998) The heme prosthetic group of lactoperoxidase. Structural characteristics of heme 1 and heme 1-peptides, J. Biol. Chem. 273, 27968-27977.
10. DePillis, G. D., Ozaki, S., Kuo, J. M., Maltby, D. A., and Ortiz De Montellano, P. R. (1997) Autocatalytic processing of heme by lactoperoxidase produces the native protein-bound prosthetic group, J. Biol. Chem. 272, 8857-8860.
11. Colas, C., Kuo, J. M., and Ortiz De Montellano, P. R. (2002) Asp-225 and Glu-375 in autocatalytic attachment of the prosthetic heme group of lactoperoxidase, J. Biol. Chem. 277, 7191-7200.
12. Guan, X., Fisher, M. B., Lang, D. H., Zheng, Y. M., Koop, D. R., and Rettie, A. E. (1998) Cytochrome P450-dependent desaturation of lauric acid: isoform selectivity and mechanism of formation of 11-dodecenoic acid, Chem.-Biol. Interact. 110, 103-121.
13. Cheesman, M. J., Baer, B. R., Zheng, Y. M., Gillam, E. M., and Rettie, A. E. (2003) Rabbit CYP4B1 engineered for high-level expression in Escherichia coli: ligand stabilization and processing of the N-terminus and heme prosthetic group, Arch. Biochem. Biophys. 416, 17-24.
14. Zheng, Y. M., Fisher, M. B., Yokotani, N., Fujii-Kuriyama, Y., and Rettie, A. E. (1998) Identification of a meander region proline residue critical for heme binding to cytochrome P450: implications for the catalytic function of human CYP4B1, Biochemistry 37, 12847-12851.
15. Watanabe, S., Varsalona, F., Yoo, Y. C., Guillaume, J. P., Bollen, A., Shimazaki, K., and Moguilevsky, N. (1998) Recombinant bovine lactoperoxidase as a tool to study the heme environment in mammalian peroxidases, FEBS Lett. 441, 476-479.
16. Ator, M. A., and Ortiz De Montellano, P. R. (1987) Protein control of prosthetic heme reactivity. Reaction of substrates with the heme edge of horseradish peroxidase, J. Biol. Chem. 262, 1542-1551.
17. Watanabe, S., Murata, S., Kumura, H., Nakamura, S., Bollen, A., Moguilevsky, N., and Shimazaki, K. (2000) Bovine lactoperoxidase and its recombinant: comparison of structure and some biochemical properties, Biochem. Biophys. Res. Commun. 274, 756-761.
18. Baer, B. R., Rettie, A. E., and Henne, K. R. (2005) Bioactivation of 4-ipomeanol by CYP4B1: adduct characterization and evidence for an enedial intermediate, Chem. Res. Toxicol. 18, 855-864.
19. 5 based on individual assignments of the 1H-NMR lines of the heme group and selected amino acid residues, Biochim. Biophys. Acta 621, 204-217.
20. 5, Biochemistry 29, 9623-9631.
21. 5. Factors determining the heterogeneous binding of the heme, Eur. J. Kochern. 267, 755-766.
22. Leys, D., Mowat, C. G., Mclean, K. J., Richmond, A., Chapman, S. K., Walkinshaw, M. D., and Munro, A. W. (2003) Atomic structure of Mycobacterium tuberculosis CYP121 to 1.06 Å reveals novel features of cytochrome P450, J. Biol. Chem. 278, 5141-5147.
23. Podust, L. M., Kim, Y., Arase, M., Neely, B. A., Beck, B. J., Bach, H., Sherman, D. H., Lamb, D. C., Kelly, S. L., and Waterman, M. R. (2003) The 1.92-Å structure of Streptomyces coelicolor A3(2) CYP154C1. A new monooxygenase that functionalizes macrolide ring systems, J. Biol. Chem. 278, 12214-12221.
24. Ortiz De Montellano, P. R., Kunze, K. L., and Beilan, H. S. (1983) Chiral orientation of prosthetic heme in the cytochrome P-450 active site, J. Biol. Chem. 258, 45-47.
25. Zgoda, G. V., Arison, B., Mkrtchian, S., Ingelman-Sundberg, M., and Almira Correia, M. (2002) Hemin-mediated restoration of allylisopropylacetamide- inactivated CYP2B1: a role for glutathione and GRP94 in the heme-protein assembly, Arch. Biochem. Biophys. 408, 58-68.
26. Inoue, E., Takahashi, Y., Imai, Y., and Kamataki, T. (2000) Development of bacterial expression system with high yield of CYP3A7, a human fetus-specific form of cytochrome P450, Biochem. Biophys. Res. Commun. 269, 623-627.
27. Imaoka, S., Hayashi, K., Hiroi, T., Yabusaki, Y., Kamataki, T., and Funae, Y. (2001) A transgenic mouse expressing human CYP4B1 in the liver, Biochem. Biophys. Res. Commun. 284, 757-762.
28. Rodrigues, A. D. (1999) Integrated cytochrome P450 reaction phenotyping: attempting to bridge the gap between cDNA-expressed cytochromes P450 and native human liver microsomes, Biochem. Pharmacol. 57, 465-480.
29. 5, J. Am. Chem. Soc. 110, 6234-6240.