Toluene monooxygenase-catalyzed epoxidation of alkenes

Applied and Environmental Microbiology

Volumn 66, Issue 5, 2000, Pages 1877-1882

  McClay, Kevin ^a   Fox, Brian G ^b   Steffan, Robert J ^a,c  

^a The Shaw Group Inc   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

^c NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BACTERIAL ENZYME; EPOXIDE; TOLUENE; UNSPECIFIC MONOOXYGENASE;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; ENZYME ACTIVITY; ENZYME SUBSTRATE; EPOXIDATION; ESCHERICHIA COLI; NONHUMAN; PSEUDOMONAS;

ALKENES; CLONING, MOLECULAR; EPOXY COMPOUNDS; ESCHERICHIA COLI; ISOENZYMES; KINETICS; OXYGENASES; PSEUDOMONAS; RECOMBINANT PROTEINS; SUBSTRATE SPECIFICITY;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; NEGIBACTERIA; PSEUDOMONAS; PSEUDOMONAS MENDOCINA;

EID: 0034017416     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/AEM.66.5.1877-1882.2000     Document Type: Article

References (24)

1. Archelas, A., and R. Furstoss. 1997. Synthesis of enantiopure epoxides through biocatalytic approaches. Annu. Rev. Microbiol. 51:491-525.
2. Besse, P., and H. Veschambre. 1994. Chemical and biological synthesis of chiral epoxides. Tetrahedron 50:8885-8927.
3. Byrne, A. M., J. J. Kukor, and R. H. Olsen. 1995. Sequence analysis of the gene cluster encoding toluene-3-monooxygenase from Pseudomonas pickettii PKO1. Gene 154:65-70.
4. Fox, B. G., J. G. Borneman, L. P. Wackett, and J. D. Lipscomb. 1990 Haloalkene oxidation by the soluble methane monooxygenase from Methylosinus trichosporium OB3b: mechanistic and environmental implications. Biochemistry 29:6419-6427.
5. Gray, K. M., and E. P. Greenberg. 1992. Physical and functional maps of the luminescence gene cluster in an autoinducer-deficient Vibrio fischeri strain isolated from a squid light organ. J. Bacteriol. 174:4384-4390.
6. Habets-Crutzen, A. Q. H., S. J. N. Carlier, J. A. M. de Bont, D. Wistuba, V. Schurig, S. Hartmans, and J. Tramper. 1985. Stereospecific formation of 1,2-epoxypropane, 1,2-epoxybutane, and 1-chloro-2,3-epoxypropane by alkene utilizing bacteria. Enzyme Microb. Technol. 7:17-21.
7. Habets-Crutzen, A. Q. H., L. E. S. Brink, C. G. van Ginkel, J. A. M. de Bont, and J. Tramper. 1984. Production of epoxides from gaseous alkenes by resting-cell suspensions and immobilized cells of alkene-utilizing bacteria. Appl. Microbiol. Biotechnol. 20:245-250.
8. Hareland, W. A., R. L. Crawford, P. J. Chapman, and S. Dagley. 1975 Metabolic function and properties of 4-hydroxyphenylacetic acid 1-hydroxylase from Pseudomonas acidovorans. J. Bacteriol. 121:272-285.
9. Jahng, D., and T. K. Wood. 1994. Trichloroethylene and chloroform degradation by a recombinant pseudomonad expressing soluble methane monooxygenase from Methylosinus trichosporium OB3b. Appl. Environ. Microbiol. 60:2473-2482.
10. Lalonde, J. 1997. Enzyme catalysis: cleaner, safer, energy efficient. Chem. Eng. 9:108-112.
11. Lange, C. C., and L. P. Wackett. 1997. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J. Bacteriol. 179:3858-3865.
12. May, S. W., M. S. Steltenkamp, R. D. Schwartz, and C. J. McCoy. 1976 Stereoselective formation of diepoxides by an enzyme system of Pseudomonas olevorans. J. Am. Chem. Soc. 98:7856-7858.
13. McClav, K., B. G. Fox, and R. J. Steffan. 1996. Chloroform mineralization by toluene-oxidizing bacteria. Appl. Environ. Microbiol. 62:2716-2722.
14. Oldenhuis, R., J. Y. Oedzes, J. J. van der Waarde, and D. B. Janssen. 1991. Kinetics of chlorinated hydrocarbon degradation by Methylosinus trichosporium OB3b and toxicity of trichloroethylene. Appl. Environ. Microbiol. 57:7-14.
15. Ono, M., and I. Okura. 1990. On the reaction mechanisms of alkene epoxidation with Methylosinus trichosporium OB3b. J. Mol. Catal. 61:113-122.
16. Panke, S., B. Witholt, A. Schmid, and M. G. Wubbolts. 1998. Towards a biocatalyst for (S)-styrene oxide production: characterization of the styrene degradation pathway of Pseudomonas sp. strain VLB120 Appl. Environ. Microbiol. 64:2032-2043.
17. Pikus, J. D., J. M. Studts, K. McClay, R. J. Steffan, and B. G. Fox. 1997. Changes in the regiospecificity of aromatic hydroxylation produced by active site engineering in the diiron enzyme toluene 4-monooxygenase. Biochemistry 36:9283-9289.
18. Shields, M. S., S. O. Montgomery, P. J. Chapman, S. M. Cuskey, and P. H. Pritchard. 1989. Novel pathway of toluene catabolism in the trichloroethylene-degrading bacterium G4. Appl. Environ. Microbiol. 55:1624-1629.
19. Stinson, S. C. 1998. Counting on chiral drugs. Chem. Eng. News 76:1-36.
20. van Hylckama, J. E. T. Vlieg, W. de Koning, and D. B. Janssen. 1996. Transformation kinetics of chlorinated ethenes by Methylosinus trichosporium OB3b and detection of unstable epoxides by on-line chromatography. Appl. Environ. Microbiol. 62:3304-3312.
21. Yeager, C. M., P. J. Bottomley, D. J. Arp, and M. R. Hyman. 1999. Inactivation of toluene 2-monooxygenase in Burkholderia cepacia G4 by alkynes. Appl. Environ. Microbiol. 65:632-639.
22. Yen, K.-M., M. R. Karl, L. M. Blatt, M. J. Simon, R. B. Winter, P. R. Fausset, H. S. Lu, A. A. Harcourt, and K. K. Chen. 1991. Cloning and characterization of a Pseudomonas mendocina KR1 gene cluster encoding toluene-4-monooxygenase. J. Bacteriol. 173:5315-5327.
23. Zhou, N.-Y., A. Jenkins, K. N. Chan, C. K. Chion, and D. J. Leak. 1998. The alkene monooxygenase from Xanthobacter PY2 is a binuclear non-haem iron protein closely related to toluene-4-monooxygenase. FEBS Lett. 430:181-185.
24. Zylstra, G. J., W. R. McCombie, D. T. Gibson, and B. A. Finette. 1988. Toluene degradation by Pseudomonas putida Fl: genetic organization of the tod operon. Appl. Environ. Microbiol. 54:1498-1503.