Regiospecific oxidation of naphthalene and fluorene by toluene monooxygenases and engineered toluene 4-monooxygenases of Pseudomonas mendocina KR1

Biotechnology and Bioengineering

Volumn 90, Issue 1, 2005, Pages 85-94

  Tao, Ying ^a   Bentley, William E ^b   Wood, Thomas K ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b UNIVERSITY OF MARYLAND   (United States)

Author keywords

Fluorene; Naphthalene; Regiospecific oxidation; Toluene monooxygenase

Indexed keywords

ENZYMES; ESCHERICHIA COLI; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; OXIDATION; POLYCYCLIC AROMATIC HYDROCARBONS; PROTEINS; SYNTHESIS (CHEMICAL); TOLUENE;

FLUORENE; MUTATIONS; REGIOSPECIFIC OXIDATION;

NAPHTHALENE;

1 HYDROXYFLUORENE; 1 NAPHTHOL; 1,7 NAPHTHALENEDIOL; 2 FLUORENOL; 2 NAPHTHOL; 2,3 NAPHTHALENEDIOL; 2,7 NAPHTHALENEDIOL; 3 HYDROXYFLUORENE; 3,6 DIHYDROXYFLUORENE; 4 HYDROXYFLUORENE; FLUORENE; FLUORENE DERIVATIVE; NAPHTHALENE; NAPHTHALENE 2,6 DIOL; NAPHTHALENE DERIVATIVE; OXYGENASE; POLYCYCLIC AROMATIC HYDROCARBON; TOLUENE; TOLUENE 4 MONOOXYGENASE; TOLUENE MONOOXYGENASE; TOLUENE ORTHO MONOOXYGENASE; TOLUENE ORTHO XYLENE MONOOXYGENASE; TOLUENE PARA MONOOXYGENASE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ARTICLE; BACTERIAL METABOLISM; BACTERIAL STRAIN; BURKHOLDERIA CEPACIA; CHEMICAL REACTION; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME ENGINEERING; ENZYME MECHANISM; ENZYME SPECIFICITY; ESCHERICHIA COLI; GAS CHROMATOGRAPHY; GENE MUTATION; MASS SPECTROMETRY; NONHUMAN; OXIDATION; PROTEIN EXPRESSION; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS MENDOCINA; PSEUDOMONAS STUTZERI; RALSTONIA; RALSTONIA PICKETTII; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; WILD TYPE;

BIODEGRADATION, ENVIRONMENTAL; ENZYME ACTIVATION; ESCHERICHIA COLI; FLUORENES; NAPHTHALENES; OXIDATION-REDUCTION; OXYGENASES; PROTEIN ENGINEERING; PSEUDOMONAS MENDOCINA; SUBSTRATE SPECIFICITY; TOLUENE;

EID: 17444385968     PISSN: 00063592     EISSN: None     Source Type: Journal    
DOI: 10.1002/bit.20414     Document Type: Article

References (51)

1. Bertoni G, Martino M, Galli E, Barbieri P. 1998. Analysis of the gene cluster encoding toluene/o-xylene monooxygenase from Pseudomonas stutzeri OX1. Appl Environ Microbiol 64:3626-3632.
2. 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.
3. Cafaro V, Scognamiglio R, Viggiani A, Izzo V, Passaro I, Notomista E, Piaz FD, Amoresano A, Casbarra A, Pucci P, et al. 2002. Expression and purification of the recombinant subunits of toluene/o-xylene monooxygenase and reconstitution of the active complex. Eur J Biochem 269:5689-5699.
4. Canada KA, Iwashita S, Shim H, Wood TK. 2002. Directed evolution of toluene ortho-monooxygenase for enhanced 1-naphthol synthesis and chlorinated ethene degradation. J Bacteriol 184:344-349.
5. Casellas M, Grifoll M, Bayona JM, Solanas AM. 1997. New metabolites in the degradation of fluorene by Arthrobacter sp. strain F101. Appl Environ Microbiol 63:819-826.
6. Cerniglia CE. 1984. Microbial metabolism of polycyclic aromatic compounds. Adv Appl Microbiol 30:31-71.
7. Chauhan S, Barbieri P, Wood TK. 1998. Oxidation of trichloroethylene, 1,1,-dichloroethylene, and chloroform by toluene/o-xylene monooxygenase from Pseudomonas stutzeri OX1. Appl Environ Microbiol 64:3023-3024.
8. Cheung P-Y, Kinkle BK. 2001. Mycobacterium diversity and pyrene mineralization in petroleum-contaminated soils. Appl Environ Microbiol 67:2222-2229.
9. Dolfing J, van den Wijngaard AJ, Janssen DB. 1993. Microbiological aspects of the removal of chlorinated hydrocarbons from air. Biodegradation 4:261-282.
10. cam. FEBS Lett 424:271-274.
11. Evans WC, Fernley HN, Griffiths E. 1965. Oxidative metabolism of phenanthrene and anthracene by soil pseudomonads. The ring fission mechanism. Biochem J 95:819-821.
12. Finkelstein ZI, Baskunov BP, Golovlev EL, Vervoort J, Rietjens IMCM, Baboshin MA, Golovleva LA. 2003. Fluorene transformation by bacteria of the genus Rhodococcus. Microbiology 72: 660-665.
13. Fishman A, Tao Y, Bentley WE, Wood TK. 2004a. Protein engineering of toluene 4-monooxygenase of Pseudomonas mendocina KR1 for synthesizing 4-nitrocatechol from nitrobenzene. Biotechnol Bioeng 87:779-790.
14. Fishman A, Tao Y, Wood TK. 2004b. Toluene 3-monooxygenase of Ralstonia pickettii PKO1 is a para-hydroxylating enzyme. J Bacteriol 186:3117-3123.
15. Folsom BR, Chapman PJ. 1991. Performance characterization of a model bioreactor for the biodegradation of trichloroethylene by Pseudomonas cepacia G4. Appl Environ Microbiol 57:1602-1608.
16. Grifoll M, Casellas M, Bayona JM, Solanas AM. 1992. Isolation and characterization of a fluorene-degrading bacterium: identification of ring oxidation and ring fission products. Appl Environ Microbiol 58:2910-2917.
17. Guerin WF, Jones GE. 1988. Mineralization of phenanthrene by a Mycobacterium sp. Appl Environ Microbiol 54:937-944.
18. Howe-Grant M (ed.). 1991. Kirk-Othmer encyclopedia of chemical technology, 4th ed. New York: Wiley-Interscience. p 994-1017.
19. Janikowski TB, Velicogna D, Punt M, Daugulis AJ. 2002. Use of a two-phase partitioning bioreactor for degrading polycyclic aromatic hydrocarbons by a Sphingomonas sp. Appl Microbiol Biotechnol 59: 368-376.
20. Laor Y, Strom PF, Farmer WJ. 1999. Bioavailability of phenanthrene sorbed to mineral-associated humic acid. Water Res 33:1719-1729.
21. Leahy JG, Batchelor PJ, Morcomb SM. 2003. Evolution of the soluble diiron monooxygenases. FEMS Microbiol Rev 27:449-479.
22. McClay K, Fox BG, Steffan RJ. 1996. Chloroform mineralization by toluene-oxidizing bacteria. Appl Environ Microbiol 62:2716-2722.
23. Newman LM, Wackett LP. 1995. Purification and characterization of toluene 2-monooxygenase from Burkholderia cepacia G4. Biochemistry 34:14066-14076.
24. Nojiri H, Nam J-W, Kosaka M, Morii K-I, Takemura T, Furihata K, Yamane H, Omori T. 1999. Diverse oxygenations catalyzed by carbazole 1,9a-dioxygenase from Pseudomonas sp. strain CA10. J Bacteriol 181:3105-3113.
25. 1 Acid-dependent high regioselectivity hydroxylation of naphthalene with hydrogen peroxide giving 1- or 2-naphthol. J Org Chem 56:6148-6151.
26. Olsen RH, Kukor JJ, Kaphammer B. 1994. A novel toluene-3-monooxygenase pathway cloned from Pseudomonas pickettii PKO1. J Bacteriol 176:3749-3756.
27. Oppenheim SF, Studts JM, Fox BG, Dordick JS. 2001. Aromatic hydroxylation catalyzed by toluene 4-monooxygenase in organic solvent/aqueous buffer mixtures. Appl Biochem Biotechnol 90: 187-197.
28. Perry RH, Chilton CH. 1973. Chemical engineers' handbook, 5th ed. New York: McGraw-Hill. p 3-39.
29. Pikus JD, Studts JM, McClay K, Steffan RJ, Fox BG. 1997. Changes in the regiospecificity of aromatic hydroxylation produced by active site engineering in the diiron enzyme toluene 4-monooxygenase. Biochemistry 36:9283-9289.
30. Prabhu Y, Phale PS. 2003. Biodegradation of phenanthrene by Pseudomonas sp. strain PP2: novel metabolic pathway, role of biosurfactant and cell surface hydrophobicity in hydrocarbon assimilation. Appl Microbiol Biotechnol 61:342-351.
31. Resnick SM, Gibson DT. 1996. Regio- and stereospecific oxidation of fluorene, dibenzofuran, and dibenzothiophene by naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4. Appl Environ Microbiol 62:4073-4080.
32. Rui L, Kwon YM, Fishman A, Reardon KF, Wood TK. 2004. Saturation mutagenesis of toluene ortho-monooxygenase for enhanced 1-naphthol synthesis and chloroform degradation. Appl Environ Microbiol 70:3246-3252.
33. Ryoo D, Shim H, Canada K, Barbieri P, Wood TK. 2000. Aerobic degradation of tetrachloroethylene by toluene-o-xylene monooxygenase of Pseudomonas stutzeri OX1. Nat Biotechnol 18:775-778.
34. Sambrook J, Fritsch EF, Maniatis T. 1989. Molecular cloning, a laboratory manual. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press.
35. Schocken MJ, Gibson DT. 1984. Bacterial oxidation of the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene. Appl Environ Microbiol 48:10-16.
36. Selifonov SA, Grifoll M, Eaton RW, Chapman PJ. 1996. Oxidation of naphthenoaromatic and methyl-substituted aromatic compounds by naphthalene 1,2-dioxygenase. Appl Environ Microbiol 62:507-514.
37. Sello G, Bernasconi S, Orsini F, Tansi M, Galli E, Di Gennaro P, Bestetti G. 2004. Organic phase effect in the biphasic bioconversion of substituted naphthalenes by engineered E. coli containing P. fluorescens N3 dioxygenase. J Mol Catal B Enzym 29:181-186.
38. Shields MS, Montgomery SO, Chapman PJ, Cuskey SM, Pritchard PH. 1989. Novel pathway of toluene catabolism in the trichloroethylene-degrading bacterium G4. Appl Environ Microbiol 55: 1624-1629.
39. Shim H, Ryoo D, Barbieri P, Wood TK. 2001. Aerobic degradation of mixtures of tetrachloroethylene, trichloroethylene, dichloroethylenes, and vinyl chloride by toluene-o-xylene monooxygenase of Pseudomonas stutzeri OX1. Appl Microbiol Biotechnol 56:265-269.
40. Shindo K, Ohnishi Y, Chun H-K, Takahashi H, Hayashi M, Saito A, Iguchi K, Furukawa K, Harayama S, Horinouchi S, et al. 2001. Oxygenation reactions of various tricyclic fused aromatic compounds using Escherichia coli and Streptomyces lividans transformants carrying several arene dioxygenase genes. Biosci Biotechnol Biochem 65: 2472-2481.
41. Smith RV, Posazza JP. 1974. Microbial models of mammalian metabolism. Aromatic hydroxylation. Arch Biochem Biophys 161: 551-558.
42. Smith RV, Humphrey DW, Engel KO, Rosazza JP. 1976. Microbial models of mammalian metabolism: aromatics hydroxylation of isomeric xylenes. Appl Environ Microbiol 31:448-449.
43. Sun AK, Wood TK. 1996. Trichloroethylene degradation and mineralization by pseudomonads and Methylosinus trichosporium OB3b. Appl Microbiol Biotechnol 45:248-256.
44. Tao Y, Fishman A, Bentley WE, Wood TK. 2004a. Altering toluene 4-monooxygenase by active site engineering for the synthesis of 3-methoxycatechol, methoxyhydroquinone, and methylhydroquinone. J Bacteriol 186:4705-4713.
45. Tao Y, Fishman A, Bentley WE, Wood TK. 2004b. Oxidation of benzene to phenol, catechol, and 1,2,3-trihydroxybenzene by toluene 4-monooxygenase of Pseudomonas mendocina KR1 and toluene 3-monooxygenase of Ralstonia pickettii PKO1. Appl Environ Microbiol 70:3814-3820.
46. Vardar G, Wood TK. 2004. Protein engineering of toluene-o-xylene monooxygenase from Pseudomonas stutzeri OX1 for synthesizing 4-methylresorcinol, methylhydroquinone, and pyrogallol. Appl Environ Microbiol 70:3253-3262.
47. Vardar G, Ryu K, Wood TK. 2005. Protein engineering of toluene-o-xylene monooxygenase from Pseudomonas stutzeri OX1 for oxidizing nitrobenzene to 3-nitrocatechol, 4-nitrocatechol, and nitrohydroquinone. J Biotechnol 115:145-156.
48. Whited GM, Gibson DT. 1991. Toluene-4-monooxygenase, a three-component enzyme system that catalyzes the oxidation of toluene to p-cresol in Pseudomonas mendocina KR1. J Bacteriol 173: 3010-3016.
49. Yamazoe A, Yagi O, Oyaizu H. 2004. Biotransformation of fluorene, diphenyl ether, dibenzo-p-dioxin and carbazole by Janibacter sp. Biotechnol Lett 26:479-486.
50. Yen K-M, Karl MR. 1992. Identification of a new gene, tomF, in the Pseudomonas mendocina KR1 gene cluster encoding toluene-4-monooxygenase. J Bacteriol 174:7253-7261.
51. Yen K-M, Karl MR, Blatt LM, Simon MJ, Winter RB, Fausset PR, Lu HS, Harcourt AA, Chen KK. 1991. Cloning and characterization of a Pseudomonas mendocina KR1 gene cluster encoding toluene-4-monooxygenase. J Bacteriol 173:5315-5327.