Microbial transformation of benzene to cis-3,5-cyclohexadien-1,2-diols by recombinant bacteria harboring toluene dioxygenase gene tod

Applied Microbiology and Biotechnology

Volumn 74, Issue 1, 2007, Pages 43-49

  Ouyang, Shao Ping ^a   Sun, Shang Yu ^a   Liu, Qian ^a   Chen, Jinchun ^a   Chen, Guo Qiang ^a,b  

^a TSINGHUA UNIVERSITY   (China)

^b SHANTOU UNIVERSITY   (China)

Author keywords

Aeromonas hydrophila; Benzene cis diols; Biotransformation; cis 3,5 Cyclohexadien 1,2 diols; Pseudomonas putida; Pseudomonas stutzeri; Toluene dioxygenase

Indexed keywords

AEROMONAS HYDROPHILA; BENZENE CIS-DIOLS; BIOTRANSFORMATION; PSEUDOMONAS PUTIDA; PSEUDOMONAS STUTZERI; TOLUENE DIOXYGENASE;

BACTERIA; ESCHERICHIA COLI; GENES; PHASE TRANSITIONS; SULFUR COMPOUNDS; TOLUENE;

BENZENE;

BENZENE; BENZENE DERIVATIVE; DIOXYGENASE; TOLUENE DIOXYGENASE; UNCLASSIFIED DRUG;

BACTERIUM; BENZENE; BIOTRANSFORMATION; CATALYSIS; ENZYME; GENE; MICROBIAL ACTIVITY; RECOMBINATION;

AEROMONAS HYDROPHILA; ARTICLE; BACTERIAL GENE; BACTERIAL STRAIN; BACTERIUM CULTURE; BACTERIUM TRANSFORMATION; BIOCATALYST; CONTROLLED STUDY; CULTURE MEDIUM; ESCHERICHIA COLI; GENE EXPRESSION; GENETIC RECOMBINATION; NONHUMAN; PLASMID; PSEUDOMONAS PUTIDA; PSEUDOMONAS STUTZERI; SPECIES COMPARISON; SPECIES CULTIVATION;

AEROMONAS HYDROPHILA; BENZENE; BIOTECHNOLOGY; CYCLOHEXANOLS; FERMENTATION; GENETIC ENGINEERING; OXYGENASES; PLASMIDS; PSEUDOMONAS PUTIDA; PSEUDOMONAS STUTZERI; RECOMBINANT PROTEINS;

AEROMONAS HYDROPHILA; ESCHERICHIA COLI; PSEUDOMONAS PUTIDA; PSEUDOMONAS STUTZERI;

EID: 33846646918     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-006-0637-6     Document Type: Article

References (30)

1. Bagneris C, Cammack R, Mason JR (2005) Subtle Difference between Benzene and Toluene Dioxygenases of Pseudomonas putida. Appl Environ Microbiol 71:1570-1580
2. Butler CS, Mason JR (1997) Structure-function analysis of the bacterial aromatic ring-hydroxylating dioxygenases. Adv Microb Physiol 38:47-84
3. Cavalca L, Amico ED, Andreoni V (2004) Intrinsic bioremediability of an aromatic hydrocarbon-polluted groundwater: diversity of bacterial population and toluene monoxygenase genes. Appl Microbiol Biotechnol 64:576-587
4. Chen GQ, Zhang G, Park SJ, Lee SY (2001) Industrial production of poly(hydroxybutyrate-co-hydroxyhexanoate). Appl Microbiol Biotechnol 57:50-55
5. Chen JY, Liu T, Zheng Z, Chen JC, Chen GQ (2004) Polyhydroxyalkanoate synthases PhaC1 and PhaC2 from Pseudomonas stutzeri 1317 had different substrate specificities. FEMS Microbiol Lett 234:231-237
6. Costura RK, Alvarez PJJ (2000) Expression and longevity of toluene dioxygenase in Pseudomonas putida F1 induced at different dissolved oxygen concentrations. Water Res 34:3014-3018
7. Friemann R, Ivkovic-Jensen MM, Lessner DJ, Yu CL, Gibson DT, Parales RE, Eklund H, Ramaswamy S (2005) Structural insight into the dioxygenation of nitroarene compounds: the crystal structure of nitrobenzene dioxygenase. J Mol Biol 348:1139-1151
8. Hack CJ, Woodley JM, Lilly MD, Liddell JM (1994) The production of Pseudomonas putida for the hydroxylation of toluene to its cis-glycol. Appl Microbiol Biotechnol 41:495-499
9. Heald SC, Jenkins RO (1996) Expression and substrate specificity of the toluene dioxygenase of Pseudomonas putida NCIMB 11767. Appl Microbiol Biotechnol 45:56-62
10. Hudlicky T, Thorpe AJ (1996) Current status and future perspectives of cyclohexadiene-cis-diols in organic synthesis: versatile intermediates in the concise design of natural products. Chem Commun 1993-2000
11. Hudlicky T, Abboud KA, Entwistle DA, Fan RL, Maurya R, Thorpe AJ, Bolonick J, Myers B (1996) Toluene-dioxygenase-mediated cis-dihydroxylation of aromatics in enantioselective synthesis - iterative glycoconjugate coupling strategy and combinatorial design for the synthesis of oligomers of nor-saccharides, inositols and pseudosugars with interesting molecular properties. Synthesis 7:897-905
12. Jiménez JI, Miñambres B, García JL, Díaz E (2002) Genomic analysis of the aromatic catabolic pathways from Pseudomonas putida KT2440. Environ Microbiol 4:824-841
13. Kellerhals MB, Kessler B, Witholt B (1999) Closed-loop control of bacterial high-cell-density fed-batch cultures: production of mcl-PHAs by Pseudomonas putida KT2442 under single-substrate and cofeeding conditions. Biotechnol Bioeng 65:306-315
14. Kim SY, Jung J, Lim Y, Ahn JH, Kim SI, Hur HG (2003) cis-2′, 3′-Dihydrodiol production on flavone B-ring by biphenyl dioxygenase from Pseudomonas pseudoalcaligenes KF707 expressed in Escherichia coli. Antonie Van Leeuwenhoek 84:261-268
15. Kovach ME, Elzer PH, Hill DS, Robertson, GT, Farris MA, Roop II RM, Peterson KM (1995) Four new derivatives of the broad-host range cloning vector pBBR1MCS, carrying different antibiotic-resistance cassettes. Gene 166:175-176
16. Ouyang SP, Han J, Qiu YZ, Qin LF, Chen S, Wu Q, Leski ML, Chen GQ (2005) Poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) production in recombinant Aeromonas hydrophila 4AK4 harboring phbA, phbB and vgb genes. Macromol Symp 224:21-34
17. Parales RE, Haddock JD (2004) Biocatalytic degradation of pollutants. Curr Opin Biotech 15:374-379
18. Qiu YZ, Han J, Chen GQ (2006) Metabolic engineering of Aeromonas hydrophila for the enhanced production of poly(3-hydroxybutyrate-co- 3-hydroxyhexanoate). Appl Microbiol Biotechnol 69:537-542
19. Qu XH, Chen JC, Ma QX, Sun SY, Chen GQ (2003) Biotransformation of benzene to cis-1,2-dihydroxycyclohexa-3,5-diene using recombinant Escherichia coli JM109 (pKST11). Sheng Wu Gong Cheng Xue Bao 19:74-80
20. Quintana MG, Dalton H (1999) Biotransformation of aromatic compounds by immobilized bacterial strains in barium alginate beads. Enzyme Microb Technol 24:232-236
21. Raschke H, Meier M, Burken JG, Hany R, Muller MD, Van Der Meer JR, Kohler HPE (2001) Biotransformation of various substituted aromatic compounds to chiral dihydrodihydroxy derivatives. Appl Environ Microbiol 67:3333-3339
22. Reddy J, Lee C, Neeper M, Greasham R, Zhang J (1999) Development of a bioconversion process for production of cis-1S,2R-indandiol from indene by recombinant Escherichia coli constructs. Appl Microbiol Biotechnol 51:614-620
23. Shindo K, Nakamura R, Osawa A, Kagami O, Kanoh K, Furukawa K, Misawa N (2005) Biocatalytic synthesis of monocyclic arene-dihydrodiols and -diols by Escherichia coli cells expressing hybrid toluene/biphenyl dioxygenase and dihydrodiol dehydrogenase genes. J Mol Catal B Enzym 35:134-141
24. Simon R, Priefer U, Pühler A (1983) A broad host range mobilization system for in vivo genetic engineering: transposon mutagenesis in gram negative bacteria. Bio/Technology 1:784-791
25. Wahbi LP, Gokhale D, Minter S, Stephens GM (1996) Construction and use of recombinant Escherichia coli strains for the synthesis of toluene cis-glycol. Enzyme Microb Technol 19:297-306
26. Wahbi LP, Phumathon1 P, Brown A, Minter S, Stephens GM (1997) Regulated toluene cis-glycol production by recombinant Escherichia coli strains constructed by PCR amplification of the toluene dioxygenase genes from Pseudomonas putida. Biotechnol Lett 19:961-965
27. Ward G, Parales RE, Dosoretz CG (2004) Biocatalytic synthesis of polycatechols from toxic aromatic compounds. Environ Sci Technol 38:4753-4757
28. Williams MG, Olson PE, Tautvydas KJ, Bitner RM, Mader RA, Wackett LP (1990) The application of toluene dioxygenase in the synthesis of acetylene-terminated resins. Appl Microbiol Biotechnol 34:316-321
29. Woo H, Sanseverino J, Cox CD, Robinson KG, Sayler GS (2000) The measurement of toluene dioxygenase activity in biofilm culture of Pseudomonas putida F1. J Microbiol Methods 40:181-191
30. Yildirim S, Franco TT, Wohlgemuth R, Kohler HPE, Witholt B, Schmid A (2005) Recombinant chlorobenzene dioxygenase from Pseudomonas sp. P51: a biocatalyst for regioselective oxidation of aromatic nitriles. Adv Synth Catal 347:1060-1072