Improving the cytochrome P450 enzyme system for electrode-driven biocatalysis of styrene epoxidation

Biotechnology Progress

Volumn 16, Issue 4, 2000, Pages 610-616

  Mayhew, Martin P ^a   Reipa, Vytautas ^a   Holden, Marcia J ^a   Vilker, Vincent L ^a  

^a NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME; EPOXIDATION;

ALPHA HYDROXYACETOPHENONE; BIOTRANSFORMATION; CYTOCHROME P450; EPOXIDATION; MUTATION; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; PUTIDAREDOXIN REDUCTASE; REACTION MECHANISM; STOICHIOMETRY; STYRENE;

BIOCONVERSION; BIOREACTORS; BIOSYNTHESIS; CATALYSIS; KETONES; REDOX REACTIONS; STOICHIOMETRY; STYRENE;

ENZYMES;

CAMPHOR 5-MONOOXYGENASE; CATALYSIS; ELECTRODES; EPOXY COMPOUNDS; HYDROXYLATION; MUTAGENESIS, SITE-DIRECTED; NAD; OXIDATION-REDUCTION; STYRENE;

EID: 0034233414     PISSN: 87567938     EISSN: None     Source Type: Journal    
DOI: 10.1021/bp000067q     Document Type: Article

References (29)

1. Crosby, J. Chirality in Industry - An Overview. In Chirality in Industy - The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; John Wiley and Sons: New York, 1992; Vol. 1, pp 47-66.
2. Furuhashi, K. Biological Routes to Optically Active Epoxides. In Chirality in Industry - The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; John Wiley and Sons: New York, 1992; Vol. 1, pp 167-186.
3. Warhurst, A. M.; Fewson, C. A. Microbial metabolism and biotransformations of styrene. J. Appl. Bacteriol. 1994, 77, 597-606.
4. Nothe, C.; Hartmans, S. Formation and degradation of styrene oxide by different microorganisms. Biocatalysis 1994, 10, 219-225.
5. Panke, S.; Witholt, B.; Schmid, A.; Wubbolts, M. G. Towards a biocatalyst for (S)-styrene oxide production: characterization of the styrene degradation pathway of Pseudomonas sp. strain VLB120. Appl. Environ. Microbiol. 1998, 64, 2032-2043.
6. cam. J. Am. Chem. Soc. 1992, 114, 6987-6993.
7. Zaks A.; Dodds, D. R. Chloroperoxidase-catalyzed asymmetric oxidations: substrate specificity and mechanistic study. J. Am. Chem. Soc. 1995, 117, 10419-10424.
8. Nickerson, D. P.; Harford-Cross, C. F.; Fulcher, S. R.; Wong, L. L. The catalytic activity of cytochrome P450cam towards styrene oxidation is increased by site-specific mutagenesis. FEBS Lett. 1997, 405, 153-156.
9. Marnett, L. J.; Weller, P.; Battista, J. R. Comparison of the peroxidase activity of hemeproteins and cytochrome P-450. In Cytochrome P-450: Structure, Mechanism, and Biochemistry; Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1986; pp 29-76.
10. Vilker, V. L.; Reipa, V.; Mayhew, M.; Holden, M. J. Challenges in capturing oxygenase activity in vitro. J. Am. Oil Chem. Soc. 1999, 76, 1283-1289.
11. cam. I. Crystallization and properties. J. Biol. Chem. 1974, 249, 94-101.
12. cam: kinetic evidence for the two-electron reduction of a high-valent ironoxo intermediate. Biochemistry 1988, 27, 1610-1616.
13. Lipscomb, J. D.; Sligar, S. G.; Namtvedt, M. J.; Gunsalus, I. C. Autoxidation and hydroxylation reactions of oxygenated cytochrome P-450cam. J. Biol. Chem. 1976, 251, 1116-1124.
14. Grayson, D. A.; Vilker, V. L. Kinetic characterization of chiral biocatalysis of cycloarenes by the camphor 5-monooxygenase system. J. Mol. Catal. B: Enzym. 1999, 6, 533-547.
15. Loida, P. J.; Sligar, S. G. Molecular recognition in cytochrome P-450: mechanism for the control of uncoupling reactions. Biochemistry 1993, 32, 11530-11538.
16. cam as revealed by site-directed mutagenesis. J. Biol. Chem. 1988, 263, 18842-18849.
17. Loida, P. J.; Sligar, S. G. Engineering cytochrome P-450cam to increase the stereospecificity and coupling of aliphatic hydroxylation. Protein Eng. 1993, 6, 207-212.
18. Reipa, V.; Mayhew, M. P.; Vilker, V. L. A direct electrodedriven P450 cycle for biocatalysis. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 13554-13558.
19. Grayson, D. A.; Tewari, Y. B.; Mayhew, M. M.; Vilker, V. L.; Goldberg, R. N. Tetralin as a substrate for camphor (cytochrome p450) 5-monooxygenase. Arch. Biochem. Biophys. 1996, 332, 239-247.
20. cam methylene monooxygenase components: cytochrome m, putidaredoxin, and putidaredoxin reductase. Methods Enzymol. 1978, 52, 166-188.
21. Roome, P. W.; Peterson, J. A. The reduction of putidaredoxin reductase by reduced pyridine nucleotides. Arch. Biochem. Biophys. 1988, 266, 32-40.
22. Yu, C.; Gunsalus, I. C. Cytochrome P-450cam. II. Interconversion with P-420. J. Biol. Chem. 1974, 249, 102-106.
23. Vinogradov, S. N. Spectrophotometric determination of iron in heme proteins. Methods Enzymol. 1986, 123, 320-323.
24. Holden, M.; Mayhew, M.; Bunk, D.; Roitberg, A.; Vilker, V. Probing the interactions of putidaredoxin with redox partners in camphor P450 5-monooxygenase by mutagenesis of surface residues. J. Biol. Chem. 1997, 272, 21720-21725.
25. Poulos, T. L.; Finzel, B. C.; Howard, A. J. High-resolution crystal structure of cytochrome P450cam. J. Mol. Biol. 1987, 195, 687-700.
26. O'Keefe, D. H.; Ebel, R. E.; Peterson, J. A. Purification of bacterial cytochrome P-450. Methods Enzymol. 1978, 52, 151-156.
27. Deprez, E.; Di Primo, C.; Hoa, G. H.; Douzou, P. Effects of monovalent cations on cytochrome P-450 camphor. Evidence for preferential binding of potassium. FEBS Lett. 1994, 347, 207-210.
28. Blumenstein, J. J.; Ukachukwu, V. C.; Mohan, R. S.; Whalen, D. L. Effects of para-substituents on the mechanisms of solvolysis of styrene oxides. J. Org. Chem. 1993, 58, 924-932.
29. Boddupalli, S. S.; Estabrook, R. W.; Peterson, J. A. Fatty acid monooxygenation by cytochrome P-450bm3. J. Biol. Chem. 1990, 265, 4233-4239.