Production of substituted naphthalene dihydrodiols by engineered Escherichia coli containing the cloned naphthalene 1,2-dioxygenase gene from Pseudomonas fluorescens N3

Research in Microbiology

Volumn 148, Issue 4, 1997, Pages 355-364

  Di Gennaro, P ^a   Galli, E ^a   Albini, G ^a   Pelizzoni, F ^a   Sello, G ^a   Bestetti, G ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

biocatalysis; dioxygenase gene; naphthalene dihydrodiol; recombinant bacteria

Indexed keywords

NAPHTHALENE; NAPHTHALENE 1,2 DIOXYGENASE; UNCLASSIFIED DRUG;

ARTICLE; BIODEGRADATION; BIOTRANSFORMATION; CATALYSIS; CONTROLLED STUDY; ESCHERICHIA COLI; GENETIC RECOMBINATION; NONHUMAN; PRIORITY JOURNAL; PSEUDOMONAS FLUORESCENS;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; PSEUDOMONAS; PSEUDOMONAS FLUORESCENS; PSEUDOMONAS PUTIDA;

EID: 0030974130     PISSN: 09232508     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0923-2508(97)81591-4     Document Type: Article

References (34)

1. Bestetti, G., Bianchi, D., Bosetti, A., Di Gennaro, P., Galli, E., Leoni, B., Pelizzoni, F. & Sello, G. (1995), Bioconversion of substituted naphthalenes to the corresponding 1,2-dihydro-1,2-dihydroxy derivatives. Determination of the regio-and stereochemistry of the oxidation reactions. Appl. Microbiol. Biotechnol., 44, 306-313.
2. Bestetti, G., Di Gennaro, P., Galli, E., Leoni, B., Pelizzoni, F., Sello, G. & Bianchi, D. (1994), Bioconversion of substituted naphthalenes to the corresponding salicylic acids. Appl. Microbiol. Biotechnol., 40, 791-793.
3. Bestetti, G., Galli, E., Ruzzi, M., Baldacci, G., Zennaro, E. & Frontali, L. (1984), Molecular characterization of a plasmid from Pseudomonas fluorescens involved in styrene degradation. Plasmid, 12, 181-188.
4. Brand, J.M., Cruden, D.L., Zylstra, G.J. & Gibson, D.T. (1992), Stereospecific hydroxylation of indan by Escherichia coli containing the cloned toluene dioxygenase genes from Pseudomonas putida F1. Appl. Environ. Microbiol., 58, 3407-3409.
5. q/Ptrp-lac plasmids and transposons that confer conditional phenotypes. Gene, 23, 17-24.
6. Dower, W.J., Miller J.F. & Ragsdale, C.W. (1988), High efficiency transformation of E. coli by high voltage electroporation. Nucleic Acids Res., 16, 6127-6145.
7. Eaton, R.W. & Chapman, P.J. (1992), Bacterial metabolism of naphthalene: construction and use of recombinant bacteria to study ring cleavage of 1,2-dihydroxynaphthalene and subsequent reactions. J. Bacteriol., 174, 7542-7554.
8. Ensley, B.D., Ratzkin, B.J., Osslund, T.D., Simon, M.J., Wackett, L.P. & Gibson, D.T. (1983), Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo. Science, 222, 167-169.
9. Franklin, F.C.H., Bagdasarian, M., Bagdasarian, M.M. & Timmis, K.N. (1981), Molecular and functional analysis of the TOL plasmid pWW0 from Pseudomonas putida and cloning of genes for the entire regulated aromatic ring meta cleavage pathway. Proc. Natl. Acad. Sci USA, 78, 7458-7462.
10. Furukawa, K. & Suzuki, H. (1988), Gene manipulation of catabolic activities for production of intermediates of various biphenyl compounds. Appl. Microbiol. Biotechnol., 29, 363-369.
11. Gibson, D.T., Zylstra, G.J. & Chauhan, S. (1989), Biotransformations catalyzed by toluene dioxygenase from Pseudomonas putida F1, in "Pseudomonas: biotransformations, pathogenesis, and evolving biotechnology" (S. Silver, A.M. Chakrabarty, B. Iglewski and S. Kaplan) (pp. 121-132).
12. Gibson, D.T., Resnick, S.M., Lee, K., Brand, J.M., Torok, D.S., Wackett, L.P., Schocken, M.J. & Haigler, B.E. (1995), Desaturation, dioxygenation, and monooxygenation reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp. strain 9816-4. J. Bacteriol., 177 2615-2621.
13. Griffin, M. & Magor, A.M. (1987), Plastics and synthetic fibers from microorganisms: a dream or a potential reality. Microbiol. Sci., 4, 357-361.
14. Hansen, J.B. & Olsen, R.H. (1978), Isolation of large bacterial plasmids and characterization of the P2 incompatibility group plasmids pMG1 and pMG5. J. Bacteriol., 135, 227-238.
15. Harayama, S., Kok, M. & Neidle, E.L. (1992), Functional and evolutionary relationships among diverse oxygenases. Ann. Rev. Microbiol., 46, 565-601.
16. Holmes, D.S. & Quigley, M. (1981), A rapid boiling method for the preparation of bacterial plasmids. Anal. Biochem., 114, 193-197.
17. Khan, A.A. & Walia, S.K. (1991), Expression, localization, and functional analysis of polychlorinated biphenyl degradation genes cbpABCD of Pseudomonas putida. Appl. Environ. Microbiol., 57, 1325-1332.
18. Khan, A.A. & Walia, S.K. (1992), Use of genetically engineered Escherichia coli strain to produce 1,2-dihydroxy-4'-chlorobiphenyl. Appl. Environ. Microbiol., 58, 1388-1391.
19. Layne, E. (1957), Spectrophotometric and turbidimetric methods for measuring protein. III. Biuret method. Methods Enzymol., 3, 447-454.
20. Maniatis, T., Fritsch, E.F. & Sambrook, J. (1982), Molecular cloning: a laboratory manual. Cold Spring Harbor Laboratory, Cold Spring Harbor, NY.
21. Mermod, N., Harayama, S. & Timmis, K.N. (1986), New route to bacterial production of indigo. Bio/Technology, 4, 321-324.
22. 2 symmetry: synthesis of (2R,3R)-dihydroxy-1,2,3,44-tetrahydronaphthalene. Tetrahedron asymmetry, 7, 1033-1040.
23. Resnick, S.M., Torok, D.S. & Gibson, D.T. (1993), Oxidation of carbazole to 3-hydroxycarbazole by naphthalene 1,2-dioxygenase and biphenyl 2,3-dioxygenase. FEMS Microbiol. Lett., 113, 297-302.
24. Resnick, S.M., Torok, D.S., Lee, K., Brand, J.M. & Gibson, D.T. (1994), Regiospecific and stereoselective hydroxylation of 1-indanone and 2-indanone by naphthalene dioxygenase and toluene dioxygenase. Appl. Environ. Microbiol., 60, 3323-3328.
25. Schell, M.A. (1985), Transcriptional control of the nah and sal hydrocarbon-degradation operons by the nahR gene product. Gene, 36, 301-309.
26. Simon, M.J., Osslund, T.D., Saunders, R., Ensley, B.D., Suggs, S., Harcourt, A., Suen, W., Cruden, D.L., Gibson, D.T. & Zylstra, G.J. (1993), Sequences of genes encoding naphthalene dioxygenase in Pseudomonas putida strains G7 and NCIB 9816-4. Gene, 127, 31-37.
27. Spain, J.C. & Gibson, D.T. (1988), Oxidation of substituted phenols by Pseudomonas putida F1 and Pseudomonas sp. strain JS6. Appl. Environ. Microbiol., 54, 1399-1404.
28. Van der Meer, J.R., de Vos, W.M., Harayama, S. & Zehnder, A.J.B. (1992), Molecular mechanisms of genetic adaptation to xenobiotic compounds. Microbiol. Rev., 56, 677-694.
29. Van den Tweel, W.J.J., Ter Berg, N., Kok, J.B. & de Bont, J.A.M. (1986), Bioformation of 4-hydroxybenzoate from 4-chlorobenzoate by Alcaligenes denitrificans NTB-1. Appl. Microbiol. Biotechnol., 25, 289-294.
30. Wubbolts, M.G., Reuvekamp, P. & Witholt, B. (1994), TOL plasmid-specified xylene oxygenase is a wide substrate range monooxygenase capable of olefin epoxidation. Enzyme Microb. Technol., 16, 608-615.
31. Wubbolts, M.G. & Timmis, K.N. (1990), Biotransformation of substituted benzoates to the corresponding cis-diols by an engineered strain of Pseudomonas oleovorans producing the TOL plasmid-specified enzyme toluate-1,2-dioxygenase. Appl. Environ. Microbiol., 56, 569-571.
32. Yamada, H. & Shimizu, S. (1988), Microbial and enzymatic processes for the production of biologically and chemically useful compounds. Angew. Chem. Int. Ed. Engl., 27, 622-642.
33. Yanisch-Perron, C., Vieira, J. & Messing, J. (1985), Improved M13 phage cloning vectors and host strains: nucleotide sequences of the M13 mp18 and pUC19 vectors. Gene, 33, 103-119.
34. Zeyer, J., Lehrbach, P. & Timmis, K.N. (1985), Use of cloned genes of Pseudomonas TOL plasmid to effect biotransformation of benzene to cis-dihydrodiols and catechols by Escherichia coli cells. Appl. Environ. Microbiol., 10, 1409-1413.