Toluene dioxygenases

Sulfoxidations are not restricted to MOs but can also be carried out by dioxygenases. For example. Pseudomonas mutant strain UV4 producing a toluene dioxygenase (TOO) and Pseudomonas NCIMB 8859 expressing a naphthalene dioxygenase (NDO) were used to oxidize aryl sulfides to antipodal chiral sulfoxides [203]. 

Jiang H, RE Parales, DT Gibson (1999) The a subunit of toluene dioxygenase from Pseudomonas putida FI can accept electrons from reduced ferredoxin oL but is catalytically inactive in the absence of the P subunit. A/)/)/. Environ. Microbiol. 65 315-318. 

Lange CC, LP Wackett (1997) Oxidation of aliphatic olefins by toluene dioxygenase enzyme rates and product identification. J Bacterial 179 3858-3865. 

Lehning A, U Fgock, R-M Wittich, KN Trmmis, DH Pieper (1997) Metabolism of chlorotoluenes by Burk-holderia sp. strain PS12 and toluene dioxygenase of Pseudomonas putida FI evidence for monooxygenation by toluene and chlorobenzene dioxygenases. Appl Environ Microbiol 63 1974-1979. 

Robertson JB, JC Spain, JD Haddock, DT Gibson (1992) Oxidation of nitrotoluenes by toluene dioxygenase evidence for a monooxygenase reaction. Appl Environ Microbiol 58 2643-2648. 

Sakamoto T, JM Joern, A Arisawa, FM Arnold (2001) Laboratory evolution of toluene dioxygenase to accept 4-picoline as a substrate Appl Environ Microbiol 67 3882-3887. 

Wackett LP, LD Kwart and DT Gibson (1988) Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putida. Biochemistry 27 1360-1367. 

Finette BA, V Subramanian, DT Gibson (1984) Isolation and characterization of Pseudomonas putida PpFl mutants defective in the toluene dioxygenase enzyme system. J Bacteriol 160 1003-1009. 

Heald S, RO Jenkins (1994) Trichloroethylene removal and oxidation toxicity mediated by toluene dioxygenase of Pseudomonas putida. Appl Environ Microbiol 60 4634-4637. 

Zylstra GJ, LP Wackett, DT Gibson (1989) Trichloroethylene degradation by Escherichia coli containing the cloned Pseudomonas putida FI toluene dioxygenase genes. Appl Environ Microbiol 55 3162-3166. 

Hydroxylation and dioxygenation are not, however, mntnally exclusive, because the toluene dioxygenase from Pseudomonasputida FI hydroxylates both phenol and 2,5-dichloro-phenol with the introduction of only one atom of oxygen (Spain et al. 1989). Snbsequent degradation by dioxygenation follows established pathways in which chloride is eliminated from muconic acids after ring fission. 

Spain JC, GJ Zylstra, CK Blake, DT Gibson (1989) Monohydroxylation of phenol and 2,5-dichlorophenol by toluene dioxygenase in Pseudomonas putida FI. Appl Environ Microbiol 55 2648-2652. 

Toluene dioxygenase-Zta gene was fused into Pseudomonas putida to eval- 210 uate toluene and trichloroethylene effects... 

Brand, J.M., Cruden, D.L., Zylstra, G.J. and Gibson, D.T., Stereospecific hydroxylation of indan by Escherichia coli containing the cloned toluene dioxygenase genes from Pseudomonasputida Vl.Appl. Environ. Microbiol., 1992, 58, 3407. 

Biological. Robertson et al. (1992) reported that toluene dioxygenases from Pseudomonas putida FI and Pseudomonas sp. Strain JS 150 oxidized the methyl group forming 2-nitrobenzyl alcohol. 

SALICYLATE 1-MONOOXYGENASE SARCOSINE OXIDASE STEROID HYDROXYLASES SULFITE OXIDASE SULEUR DIOXYGENASE THYMIDINE 2 -HYDROXYLASE TOLUENE DIOXYGENASE XANTHINE OXIDASE... 

BIOCHEMICAL NOMENCLATURE TOLUENE DIOXYGENASE TONICITY TOPAQUINONE... 

Hudlicky, T., Tian, X., Konigsberger, K., Mauiya, R., Rouden, J. and Fan, B. (1996c) Toluene-dioxygenase-mediated as-dihydroxylation of aromatics in enantioselective synthesis. Asymmetric total syntheses of pancratistatin and 7-deoxypancratistatin, promising antitumor agents. J. Am. Chem. Soc., 118, 10752-10765. 

Yeh, W. K., Gibson, D. T. Liu, Te-Ning(1977). Toluene dioxygenase a multicomponent enzyme system. Biochemical and Biophysical Research Communication, 78, 401-10. 

Incomplete aerobic transformations may involve cometabolic transformations and reactions resulting in recalcitrant dead-end metabolites. Cometabolic o-hydroxylation of MCPs and DCPs by a phenol monooxygenase has been shown, for example, in a Pseudomonas sp. (Knackmuss Hellwig, 1978) and by the toluene dioxygenase reaction in Pseudomonas putida (Spain Gibson, 1988 Spain et al., 1989)- Cometabolic transformation of CPs is also possible in aerobic mixed culture systems. Phenol- and toluene-enriched cultures completely removed 2,4-DCP, and the toluene enrichment also removed 2,4,6-TCP and PCP (Ryding et al., 1994). This PCP attack by the toluene enrichment involved an o-hydroxylation. 

Spain, J. C. Gibson, D. T. (1988). Oxidation of substituted phenols by Pseudomonasputida FI and Pseudomonas sp. strain JS6. Applied and Environmental Microbiology, 54,1399-404. Spain, J. C., Zylstra, G.J., Blake, C. K. Gibson, D. T. (1989). Monohydroxylation of phenol and 2,5-dichlorophenol by toluene dioxygenase in Pseudomonas putida PI. Applied and Environmental Microbiology, 55, 2648—52. 

Wackett, L. P. Gibson, D. T. (1988). Degradation of trichloroethylene by toluene dioxygenase in whole cell studies with Pseudomonas putida FI. Applied and Environmental Microbiology, 54, 1703-8. 

Wackett, L. P. Householder, S. R. (1989). Toxicity of trichloroethylene to Pseudomonas putida FI is mediated by toluene dioxygenase. Applied and Environmental Microbiology, 55, 2723-5. 

The toluene dioxygenase,1387 benzoate 1,2-dioxygenase1388 and pyrazon dioxygenase1389 all contain [2Fe-2S] clusters and require Fe2+, although the stoichiometries differ as shown in Table 28. It appears very probable that they all contain the [2Fe-2S]Fe2+ site for activation of dioxygen. 

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