A new biocatalyst for production of optically pure aryl epoxides by styrene monooxygenase from Pseudomonas fluorescens ST

Applied and Environmental Microbiology

Volumn 65, Issue 6, 1999, Pages 2794-2797

  Gennaro, Patrizia Di ^a   Colmegna, Andrea ^a   Galli, Enrica ^a   Sello, Guido ^a   Pelizzoni, Francesca ^a   Bestetti, Giuseppina ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; STYRENE; UNSPECIFIC MONOOXYGENASE;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; ENZYME SPECIFICITY; MOLECULAR CLONING; NONHUMAN; OXIDATION; PSEUDOMONAS FLUORESCENS;

ESCHERICHIA COLI; NEGIBACTERIA; PSEUDOMONAS; PSEUDOMONAS FLUORESCENS;

EID: 0033017776     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/aem.65.6.2794-2797.1999     Document Type: Article

References (18)

1. Beltrametti, F., A. M. Marconi, G. Bestetti, C. Colombo, E. Galli, M. Ruzzi, and E. Zennaro. 1997. Sequencing and functional analysis of styrene catabolism genes from Pseudomonas fluorescens ST. Appl. Environ. Microbiol. 63:2232-2239.
2. Conan, A., S. Sibille, and J. Perichon. 1991. Metal exchange between an electrogenerated organonickel species and zinc halide: application to an electrochemical, nickel-catalyzed Reformatsky reaction. J. Org. Chem. 56: 2018-2024.
3. Fu, M. H., and M. Alexander. 1992. Biodegradation of styrene in samples of natural environments. Environ. Sci. Technol. 26:1540-1544.
4. Furuhashi, K. 1992. Biological routes to optically active epoxides, p. 167-186. In A. N. Collins, G. N. Sheldrake, and J. Crosby (ed.), Chirality in industry. John Wiley & Sons Ltd., Chichester, United Kingdom.
5. Ghelfi, F., R. Grandi, and U. M. Pagnoni. 1995. Regiospecific conversion of α,β-epoxy acetates to 3-chloro-2-hydroxy acetates. Gazz. Chim. Ital. 125: 215-217.
6. Imuta, M., K. Kawai, and H. Ziffer. 1980. Product sterospecificity in the microbial reduction of α-haloaryl ketones. J. Org. Chem. 45:3352-3355.
7. Kloc, K., E. Kubicz, and J. Mlochowski. 1984. A novel approach to functionalization of azines. Oxiranyl and thiiranyl derivatives of pyridine, quinoline and isoquinoline. Heterocycles 22:2517-2522.
8. Legters, J., L. Thijs, and B. Zwanenburg. 1989. A convenient synthesis of optically active 1H-aziridine-2-carboxylic acids (esters). Tetrahedron Lett. 30:4881-4884.
9. Marconi, A. M., F. Beltrametti, G. Bestetti, F. Solinas, M. Ruzzi, E. Galli, and E. Zennaro. 1996. Cloning and characterization of styrene catabolism genes from Pseudomonas fluorescens ST. Appl. Environ. Microbiol. 62:121-127.
10. Matthews, B. R., W. R. Jackson, H. A. Jacobs, and K. G. Watson. 1990. Synthesis of aryl carbohydrate synthons and 2,3-dihydroxypropanoic derivatives of high optical purity. Aust. J. Chem. 43:1195-1214.
11. Nakajirna, M., K. Tomioka, Y. Iitaka, and K. Koga. 1993. Highly enantio-selective dihydroxylation of olefins by osmium tetroxide with chiral diamines. Tetrahedron 49:10793-19806.
12. Nöthe, C., and S. Hartmans. 1994. Formation and degradation of styrene oxide stereoisomers by different microorganisms. Biocatalysis 10:219-225.
13. 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.
14. Pedragosa-Moreau, S., A. Archelas, and R. Furstoss. 1996. Microbiological transformations. 32. Use of epoxide hydrolase mediated biohydrolysis as a way to enantiopure epoxide and vicinal diols: application to substituted styrene oxide derivatives. Tetrahedron 52:4593-4606.
15. Srivastava, K. C. 1990. Biodegradation of styrene by Thermophilic bacillus isolates, p. 53-58. In L. G. Copping, R. E. Martin, J. A. Picket, E. C. Buck, and A. W. Bunch (ed.), Opportunities in biotransformations. Elsevier Applied Science, London, England.
16. Utkin, I. B., M. M. Yachimov, L. N. Matveeva, E. I. Kozlyak, I. S. Rogozhin, Z. G. Solomon, and A. M. Bezborodov. 1991. Degradation of styrene and ethylbenzene by Pseudomonas species Y2. FEMS Microbiol. Lett. 77:237-242.
17. Velasco, A., S. Alonso, J. L. Garcia, J. Perera, and E. Diaz. 1998. Genetic and functional analysis of the styrene catabolic cluster of Pseudomonas sp. strain Y2. J. Bacteriol. 180:1063-1071.
18. Whitman, C. P., J. C. Craig, and G. L. Kenyon. 1985. Synthesis, chioptical properties and absolute configuration of α-phenylglicidic acid. Tetrahedron 41:1183-1192.