P450cam biocatalysis in surfactant-stabilized two-phase emulsions

Biotechnology and Bioengineering

Volumn 99, Issue 6, 2008, Pages 1311-1319

  Ryan, Jessica D ^a   Clark, Douglas S ^a  

^a University of California   (United States)

Author keywords

Emulsion; P450cam; Surfactant; Uncoupling

Indexed keywords

CAMPHOR; PHASE EMULSIONS; WATER EMULSIONS;

BIOCATALYSTS; EMULSIONS; HYDROXYLATION; PHASE TRANSITIONS;

PROTEINS;

2,5 DIOXOCAMPHANE; ALCOHOL DEHYDROGENASE; BIS(2 ETHYLHEXYL) SULFOSUCCINATE SODIUM SALT; CAMPHOR; CYTOCHROME P450; CYTOCHROME P450 OXYGENASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG; 1,4 BIS(2 ETHYLHEXYL) SODIUM SULFOSUCCINATE; 1,4-BIS(2-ETHYLHEXYL) SODIUM SULFOSUCCINATE; CAMPHOR 5 MONOOXYGENASE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SUCCINIC ACID DERIVATIVE; SURFACTANT;

ARTICLE; BIOCATALYST; EMULSION; ENZYME ACTIVATION; KINETICS; OXIDATION; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; PHASE TRANSITION;

DRYOBALANOPS;

CAMPHOR 5-MONOOXYGENASE; CATALYSIS; EMULSIONS; NADP; OXIDATION-REDUCTION; PHASE TRANSITION; SUCCINATES; SURFACE-ACTIVE AGENTS;

EID: 41049106006     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.21772     Document Type: Article

References (26)

1. Eiben S, Kaysser L, Maurer S, Kuhnel K, Urlacher VB, Schmid RD. 2006. Preparative use of isolated CYP102 monooxygenases - A critical appraisal. J Biotechnol 124(4):662-669.
2. Farinas ET, Alcalde M, Arnold F. 2004. Alkene epoxidation catalyzed by cytochrome P450BM-3 139-3. Tetrahedron 60(3):525-528.
3. Fruetel JA, Collins JR, Camper DL, Loew GH, Ortiz De Montellano PR. 1992. Calculated and experimental absolute stereochemistry of the styrene and beta-methylstyrene epoxides formed by cytochrome-P450Cam. J Am Chem Soc 114(18):6987-6993.
4. Funhoff EG, Bauer U, Garcia-Rubio I, Witholt B, van Beilen JB. 2006. CYP153A6, a soluble P450 oxygenase catalyzing terminal-alkane hydroxylation. J Bacteriol 188(14):5220-5227.
5. Grayson DA, Tewari YB, Mayhew MP, Vilker VL, Goldberg RN. 1996. Tetralin as a substrate for camphor (cytochrome P450) 5-monooxygenase. Arch Biochem Biophys 332(2):239-247.
6. Guengerich FP. 2001. Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem Res Toxicol 14(6):611-650.
7. Gunsalus IC, Wagner GC. 1978. Bacterial P450cam methylene monooxygenase components: Cytochrome m, putidaredoxin, and putidaredoxin reductase. Methods Enzymol 52C:166-188.
8. Harford-Cross CF, Carmichael AB, Allan FK, England PA, Rouch DA, Wong LL. 2000. Protein engineering of cytochrome P450cam (CYP101) for the oxidation of polycyclic aromatic hydrocarbons. Protein Eng 13(2):121-128.
9. Hartline RA, Gunsalus IC. 1971. Induction specificity and catabolite repression of the early enzymes in camphor degradation by Pseudomonas putida. J Bacteriol 106(2):468-478.
10. Ichinose H, Michizoe J, Maruyama T, Kamiya N, Goto M. 2004. Electrontransfer reactions and functionalization of cytochrome P450cam monooxygenase system in reverse micelles. Langmuir 20(13):5564-5568.
11. Jakoby W. 1980. Enzymatic basis of detoxification. New York: Academic Press. p 1-6.
12. Kenworthy KE, Bloomer JC, Clarke SE, Houston JB. 1999. CYP3A4 drug interactions: Correlation of 10 in vitro probe substrates. Br J Clin Pharmacol 48(5):716-727.
13. Loida PJ, Sligar SG. 1993. Molecular recognition in cytochrome P-450: Mechanism for the control of uncoupling reactions. Biochemistry 32(43):11530-11538.
14. Louwrier A, Drtina GJ, Klibanov AM. 1996. On the issue of interfacial activation of lipase in nonaqueous media. Biotechnol Bioeng 50(1):1-5.
15. Maruyama T, Nakajima M, Ichikawa S, Nabetani H, Furusaki S, Seki M. 2000. Oil-water interfacial activation of lipase for interesterification of triglyceride and fatty acid. J Am Oil Chem Soc 77(11):1121-1126.
16. Maurer SC, Kuhnel K, Kaysser LA, Eiben S, Schmid RD, Urlacher VB. 2005. Catalytic hydroxylation in biphasic systems using CYP102A1 mutants. Adv Synth Catal 347(7-8):1090-1098.
17. Michizoe J, Ichinose H, Kamiya N, Maruyama T, Goto M. 2005. Functionalization of the cytochrome P450cam monooxygenase system in the cell-like aqueous compartments of water-in-oil emulsions. J Biosci Bioeng 99(1):12-17.
18. Nikolova P, Ward OP. 1993. Whole cell biocatalysis in nonconventional media. J Ind Microbiol 12(2):76-86.
19. Ortiz de Montellano PR, editor. 2005. Cytochrome P450: Structure, mechanism and biochemistry. New York: Plenum Press.
20. Park JB, Clark DS. 2006. New reaction system for hydrocarbon oxidation by chloroperoxidase. Biotechnol Bioeng 94(1):189-192.
21. Paulsen MD, Filipovic D, Sligar SG, Ornstein RL. 1993. Controlling the regiospecificity and coupling of cytochrome P450cam: T185F mutant increases coupling and abolishes 3-hydroxynorcamphor product. Protein Sci 2(3):357-365.
22. Purdy MM, Koo LS, Ortiz de Montellano PR, Klinman JP. 2004. Steady-state kinetic investigation of cytochrome P450cam: Interaction with redox partners and reaction with molecular oxygen. Biochemistry 43(1):271-281.
23. Sibbesen O, De Voss JJ, Montellano PR. 1996. Putidaredoxin reductase-putidaredoxin-cytochrome P450cam triple fusion protein. Construction of a self-sufficient Escherichia coli catalytic system. J Biol Chem 271(37):22462-22469.
24. Stamatis H, Xenakis A, Kolisis FN. 1995. Studies on enzyme reuse and product recovery in lipase-catalyzed reactions in microemulsions. Enzyme Engineering Xii 750:237-241.
25. Urlacher V, Schmid RD. 2002. Biotransformations using prokaryotic P450 monooxygenases. Curr Opin Biotechnol 13(6):557-564.
26. Wong TS, Arnold FH, Schwaneberg U. 2004. Laboratory evolution of cytochrome P450 BM-3 monooxygenase for organic cosolvents. Biotechnol Bioeng 85(3):351-358.