1.14.12.11: toluene dioxygenase

This is an abbreviated version!
For detailed information about toluene dioxygenase, go to the full flat file.

Word Map on EC 1.14.12.11

Reaction

Toluene
+
NADH
+
H+
+
O2
=
(1S,2R)-3-Methylcyclohexa-3,5-diene-1,2-diol
+
NAD+

Synonyms

ISPTOD, ISPTOL, More, oxygenase, toluene 2,3-di-, oxygenaseTOL, TDO, Tod, todC1C2BA, toluene 2,3-dioxygenase

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.12 With NADH or NADPH as one donor, and incorporation of two atoms of oxygen into the other donor
                1.14.12.11 toluene dioxygenase

Reference

Reference on EC 1.14.12.11 - toluene dioxygenase

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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Subramanian, V.; Liu, T.N.; Yeh, W.K.; Narro, M.; Gibson, D.T.
Purification and properties of NADH-ferredoxinTOL reductase. A component of toluene dioxygenase from Pseudomonas putida
J. Biol. Chem.
256
2723-2730
1981
Pseudomonas putida
Manually annotated by BRENDA team
Subramanian, V.; Liu, T.N.; Yeh, W.K.; Gibson, D.T.
Toluene dioxygenase: purification of an iron-sulfur protein by affinity chromatography
Biochem. Biophys. Res. Commun.
91
1131-1139
1979
Pseudomonas putida
Manually annotated by BRENDA team
Wackett, L.P.; Kwart, L.D.; Gibson, D.T.
Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putida
Biochemistry
27
1360-1367
1988
Pseudomonas putida
Manually annotated by BRENDA team
Yeh, W.K.; Gibson, D.T.; Liu, T.N.
Toluene dioxygenase: a multicomponent enzyme system
Biochem. Biophys. Res. Commun.
78
401-410
1977
Pseudomonas putida
Manually annotated by BRENDA team
Zylstra, G.J.; Gibson, D.T.
Toluene degradation by Pseudomonas putida F1. Nucleotide sequence of the todC1C2BADE genes and their expression in Escherichia coli
J. Biol. Chem.
264
14940-14946
1989
Pseudomonas putida
Manually annotated by BRENDA team
Stephens, G.M.; Sidebotham, J.M.; Mann, N.H.; Dalton, H.
Cloning and expression in Escherichia coli of the toluene dioxygenase gene from Pseudomonas putida
FEMS Microbiol. Lett.
57
295-300
1989
Pseudomonas putida, Pseudomonas putida NCIB11767
Manually annotated by BRENDA team
Zylstra, G.J.; Wackett, L.P.; Gibson, D.T.
Trichloroethylene degradation by Escherichia coli containing the cloned Pseudomonas putida F1 toluene dioxygenase genes
Appl. Environ. Microbiol.
55
3162-3166
1989
Pseudomonas putida
Manually annotated by BRENDA team
Subramanian, V.; Liu, T.N.; Yeh, W.K.; Serdar, C.M.; Wackett, L.P.; Gibson, D.T.
Purification and properties of ferredoxinTOL. A component of toluene dioxygenase from Pseudomonas putida F1
J. Biol. Chem.
260
2355-2363
1985
Pseudomonas putida
Manually annotated by BRENDA team
Zylstra, G.J.; McCombie, W.R.; Gibson, D.T.; Finette, B.A.
Toluene degradation by Pseudomonas putida F1: genetic organization of the tod operon
Appl. Environ. Microbiol.
54
1498-1503
1988
Pseudomonas putida
Manually annotated by BRENDA team
Wackett, L.P.
Toluene dioxygenase from Pseudomonas putida F1
Methods Enzymol.
188
39-45
1990
Pseudomonas putida
Manually annotated by BRENDA team
Lange, C.C.; Wackett, L.P.
Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification
J. Bacteriol.
179
3858-3865
1997
Pseudomonas putida
Manually annotated by BRENDA team
Jiang, H.; Parales, R.E.; Gibson, D.T.
The alpha subunit of toluene dioxygenase from Pseudomonas putida F1 can accept electrons from reduced FerredoxinTOL but is catalytically inactive in the absence of the beta subunit
Appl. Environ. Microbiol.
65
315-318
1999
Pseudomonas putida
Manually annotated by BRENDA team
Lynch, N.A.; Jiang, H.; Gibson, D.T.
Rapid purification of the oxygenase component of toluene dioxygenase from a polyol-responsive monoclonal antibody
Appl. Environ. Microbiol.
62
2133-2137
1996
Pseudomonas putida
Manually annotated by BRENDA team
Jiang, H.; Parales, R.E.; Lynch, N.A.; Gibson, D.T.
Site-directed mutagenesis of conserved amino acids in the alpha subunit of toluene dioxygenase: potential mononuclear non-heme iron coordination sites
J. Bacteriol.
178
3133-3139
1996
Pseudomonas putida
Manually annotated by BRENDA team
Leahy, J.G.; Olsen, R.H.
Kinetics of toluene degradation by toluene-oxidizing bacteria as a function of oxygen concentration, and the effect of nitrate
FEMS Microbiol. Ecol.
23
23-30
1997
Pseudomonas sp., Pseudomonas putida, Pseudomonas fluorescens, Pseudomonas sp. W31, Pseudomonas fluorescens CFS215
Manually annotated by BRENDA team
Lee, K.; Brand, J.M.; Gibson, D.T.
Stereospecific sulfoxidation by toluene and naphthalene dioxygenases
Biochem. Biophys. Res. Commun.
212
9-15
1995
Pseudomonas putida
Manually annotated by BRENDA team
Li, S.; Wackett, L.P.
Trichloroethylene oxidation by toluene dioxygenase
Biochem. Biophys. Res. Commun.
185
443-451
1992
Pseudomonas putida
Manually annotated by BRENDA team
Resnick, S.M.; Torok, D.S.; Lee, K.; Brand, J.M.; Gibson, D.T.
Regiospecific and stereoselective hydroxylation of 1-indanone and 2-indanone by naphthalene dioxygenase and toluene dioxygenase
Appl. Environ. Microbiol.
60
3323-3328
1994
Pseudomonas putida, Pseudomonas putida F39D
Manually annotated by BRENDA team
Bui, V.P.; Vidar Hansen, T.; Stenstrom, Y.; Hudlicky, T.; Ribbons, D.W.
A study of substrate specificity of toluene dioxygenase in processing aromatic compounds containing benzylic and/or remote chiral centers
New J. Chem.
25
116-124
2001
Pseudomonas putida
-
Manually annotated by BRENDA team
Boyd, D.R.; Sharma, N.D.; Haughey, S.A.; Kennedy, M.A.; McMurray, B.T.; Sheldrake, G.N.; Allen, C.C.R.; Dalton, H.; Sproule, K.
Toluene and naphthalene dioxygenase-catalyzed sulfoxidation of alkyl aryl sulfides
J. Chem. Soc. Perkin Trans.
1
1929-1934
1998
Pseudomonas putida, Pseudomonas putida UV4
-
Manually annotated by BRENDA team
Bowers, N.I.; Boyd, D.R.; Sharma, N.D.; Goodrich, P.A.; Groocock, M.R.; Blacker, A.J.; Goode, P.; Dalton, H.
Stereoselective benzylic hydroxylation of 2-substituted indanes using toluene dioxygenase as biocatalyst
J. Chem. Soc. Perkin Trans.
1
1453-1462
1999
Pseudomonas putida, Pseudomonas putida UV4
-
Manually annotated by BRENDA team
Sakamoto, T.; Joern, J.M.; Arisawa, A.; Arnold, F.H.
Laboratory evolution of toluene dioxygenase to accept 4-picoline as a substrate
Appl. Environ. Microbiol.
67
3882-3887
2001
Pseudomonas putida
Manually annotated by BRENDA team
Bagneris, C.; Cammack, R.; Mason, J.R.
Subtle difference between benzene and toluene dioxygenases of Pseudomonas putida
Appl. Environ. Microbiol.
71
1570-1580
2005
Pseudomonas putida
Manually annotated by BRENDA team
Xu, Z.; Mulchandani, A.; Chen, W.
Detection of benzene, toluene, ethyl benzene, and xylenes (BTEX) using toluene dioxygenase-peroxidase coupling reactions
Biotechnol. Prog.
19
1812-1815
2003
Pseudomonas putida
Manually annotated by BRENDA team
Ni, Y.; Chen, R.R.
Lipoprotein mutation accelerates substrate permeability-limited toluene dioxygenase-catalyzed reaction
Biotechnol. Prog.
21
799-805
2005
Pseudomonas putida
Manually annotated by BRENDA team
Kim, J.Y.; Lee, K.; Kim, Y.; Kim, C.K.; Lee, K.
Production of dyestuffs from indole derivatives by naphthalene dioxygenase and toluene dioxygenase
Lett. Appl. Microbiol.
36
343-348
2003
Pseudomonas putida
Manually annotated by BRENDA team
Boyd, D.R.; Sharma, N.D.; Bowers, N.I.; Boyle, R.; Harrison, J.S.; Lee, K.; Bugg, T.D.; Gibson, D.T.
Stereochemical and mechanistic aspects of dioxygenase-catalysed benzylic hydroxylation of indene and chromane substrates
Org. Biomol. Chem.
1
1298-1307
2003
Pseudomonas putida, Pseudomonas putida UV4
Manually annotated by BRENDA team
Boyd, D.R.; Sharma, N.D.; Gunaratne, N.; Haughey, S.A.; Kennedy, M.A.; Malone, J.F.; Allen, C.C.; Dalton, H.
Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation
Org. Biomol. Chem.
1
984-994
2003
Pseudomonas putida, Pseudomonas putida UV4
Manually annotated by BRENDA team
Lee, K.; Friemann, R.; Parales, J.V.; Gibson, D.T.; Ramaswamy, S.
Purification, crystallization and preliminary X-ray diffraction studies of the three components of the toluene 2,3-dioxygenase enzyme system
Acta crystallogr. Sect. F
61
669-672
2005
Pseudomonas putida
Manually annotated by BRENDA team
Boyd, D.R.; Sharma, N.D.; Bowers, N.I.; Dalton, H.; Garrett, M.D.; Harrison, J.S.; Sheldrake, G.N.
Dioxygenase-catalysed oxidation of disubstituted benzene substrates: benzylic monohydroxylation versus aryl cis-dihydroxylation and the meta effect
Org. Biomol. Chem.
4
3343-3349
2006
Pseudomonas putida, Pseudomonas putida UV4
Manually annotated by BRENDA team
Boyd, D.R.; Sharma, N.D.; Llamas, N.M.; Coen, G.P.; McGeehin, P.K.; Allen, C.C.
Chemoenzymatic synthesis of trans-dihydrodiol derivatives of monosubstituted benzenes from the corresponding cis-dihydrodiol isomers
Org. Biomol. Chem.
5
514-522
2007
Pseudomonas putida, Pseudomonas putida UV4
Manually annotated by BRENDA team
Finn, K.J.; Collins, J.; Hudlicky, T.
Toluene dioxygenase-mediated oxidation of dibromobenzenes. Absolute stereochemistry of new metabolites and synthesis of (-)-conduritol E
Tetrahedron
62
7471-7476
2006
Escherichia coli, Escherichia coli JM 109 (pDTG601)
-
Manually annotated by BRENDA team
Finn, K.J.; Rochon, L.; Hudlicky, T.
Processing of cyclopropylarenes by toluene dioxygenase: isolation and absolute configuration of metabolites
Tetrahedron Asymmetry
16
3606-3613
2005
Escherichia coli, Escherichia coli JM 109 (pDTG601)
-
Manually annotated by BRENDA team
Ramos-Gonzalez, M.I.; Ben-Bassat, A.; Campos, M.J.; Ramos, J.L.
Genetic engineering of a highly solvent-tolerant Pseudomonas putida strain for biotransformation of toluene to p-hydroxybenzoate
Appl. Environ. Microbiol.
69
5120-5127
2003
Pseudomonas putida, Pseudomonas putida DOT-T1E
Manually annotated by BRENDA team
Morono, Y.; Unno, H.; Tanji, Y.; Hori, K.
Addition of aromatic substrates restores trichloroethylene degradation activity in Pseudomonas putida F1
Appl. Environ. Microbiol.
70
2830-2835
2004
Pseudomonas putida
Manually annotated by BRENDA team
Shingleton, J.T.; Applegate, B.A.; Baker, A.J.; Sayler, G.S.; Bienkowski, P.R.
Quantification of toluene dioxygenase induction and kinetic modeling of TCE cometabolism by Pseudomonas putida TVA8
Biotechnol. Bioeng.
76
341-350
2001
Pseudomonas putida, Pseudomonas putida TVA8
Manually annotated by BRENDA team
Lovanh, N.; Alvarez, P.J.
Effect of ethanol, acetate, and phenol on toluene degradation activity and tod-lux expression in Pseudomonas putida TOD102: evaluation of the metabolic flux dilution model
Biotechnol. Bioeng.
86
801-808
2004
Pseudomonas putida
Manually annotated by BRENDA team
Woo, H.; Sanseverino, J.; Cox, C.D.; Robinson, K.G.; Sayler, G.S.
The measurement of toluene dioxygenase activity in biofilm culture of Pseudomonas putida F1
J. Microbiol. Methods
40
181-191
2000
Pseudomonas putida
Manually annotated by BRENDA team
Zhang, N.; Stewart, B.G.; Moore, J.C.; Greasham, R.L.; Robinson, D.K.; Buckland, B.C.; Lee, C.
Directed evolution of toluene dioxygenase from Pseudomonas putida for improved selectivity toward cis-indandiol during indene bioconversion
Metab. Eng.
2
339-348
2000
Pseudomonas putida
Manually annotated by BRENDA team
Boyd, D.R.; Sharma, N.D.; Coen, G.P.; Gray, P.J.; Malone, J.F.; Gawronski, J.
Enzyme-catalysed synthesis and absolute configuration assignments of cis-dihydrodiol metabolites from 1,4-disubstituted benzenes
Chemistry
13
5804-5811
2007
Pseudomonas putida, Pseudomonas putida UV4
Manually annotated by BRENDA team
Ouyang, S.P.; Liu, Q.; Sun, S.Y.; Chen, J.C.; Chen, G.Q.
Genetic engineering of Pseudomonas putida KT2442 for biotransformation of aromatic compounds to chiral cis-diols
J. Biotechnol.
132
246-250
2007
Pseudomonas putida, Pseudomonas putida KT 2442
Manually annotated by BRENDA team
Friemann, R.; Lee, K.; Brown, E.N.; Gibson, D.T.; Eklund, H.; Ramaswamy, S.
Structures of the multicomponent Rieske non-heme iron toluene 2,3-dioxygenase enzyme system
Acta Crystallogr. Sect. D
65
24-33
2009
Pseudomonas putida
Manually annotated by BRENDA team
da Silva, M.; Alvarez, P.
Indole-based assay to assess the effect of ethanol on Pseudomonas putida F1 dioxygenase activity
Biodegradation
2009
1-6
2009
Pseudomonas putida F1
-
Manually annotated by BRENDA team
Boyd, D.R.; Sharma, N.D.; Malone, J.F.; Allen, C.C.
New families of enantiopure cyclohexenone cis-diol, o-quinol dimer and hydrate metabolites from dioxygenase-catalysed dihydroxylation of phenols
Chem. Commun. (Camb. )
2009
3633-3635
2009
Pseudomonas putida
Manually annotated by BRENDA team
Kwit, M.; Gawronski, J.; Boyd, D.R.; Sharma, N.D.; Kaik, M.; More O'Ferrall, R.A.; Kudavalli, J.S.
Toluene dioxygenase-catalyzed synthesis of cis-dihydrodiol metabolites from 2-substituted naphthalene substrates: assignments of absolute configurations and conformations from circular dichroism and optical rotation measurements
Chemistry
14
11500-11511
2008
Pseudomonas putida, Pseudomonas putida UV4
Manually annotated by BRENDA team
Hamada, T.; Maeda, Y.; Matsuda, H.; Sameshima, Y.; Honda, K.; Omasa, T.; Kato, J.; Ohtake, H.
Effect of cell-surface hydrophobicity on bacterial conversion of water-immiscible chemicals in two-liquid-phase culture systems
J. Biosci. Bioeng.
108
116-120
2009
Pseudomonas putida
Manually annotated by BRENDA team
Lacal, J.; Guazzaroni, M.E.; Busch, A.; Krell, T.; Ramos, J.L.
Hierarchical binding of the TodT response regulator to its multiple recognition sites at the tod pathway operon promoter
J. Mol. Biol.
376
325-337
2008
Pseudomonas putida
Manually annotated by BRENDA team
Busch, A.; Lacal, J.; Silva-Jimenez, H.; Krell, T.; Ramos, J.L.
Catabolite repression of the TodS/TodT two-component system and effector-dependent transphosphorylation of TodT as the basis for toluene dioxygenase catabolic pathway control
J. Bacteriol.
192
4246-4250
2010
Pseudomonas putida
Manually annotated by BRENDA team
Boyd, D.R.; Sharma, N.D.; Stevenson, P.J.; Blain, M.; McRoberts, C.; Hamilton, J.T.; Argudo, J.M.; Mundi, H.; Kulakov, L.A.; Allen, C.C.
Dioxygenase-catalysed cis-dihydroxylation of meta-substituted phenols to yield cyclohexenone cis-diol and derived enantiopure cis-triol metabolites
Org. Biomol. Chem.
9
1479-1490
2011
Pseudomonas putida, Pseudomonas putida UV4
Manually annotated by BRENDA team
Clingenpeel, S.; Moan, J.; McGrath, D.; Hungate, B.; Watwood, M.
Stable carbon isotope fractionation in chlorinated ethene degradation by bacteria expressing three toluene oxygenases
Front. Microbiol.
3
63
2012
Pseudomonas putida
Manually annotated by BRENDA team
Lin, T.Y.; Werther, T.; Jeoung, J.H.; Dobbek, H.
Suppression of electron transfer to dioxygen by charge transfer and electron transfer complexes in the FAD-dependent reductase component of toluene dioxygenase
J. Biol. Chem.
287
38338-38346
2012
Pseudomonas putida
Manually annotated by BRENDA team
Nitisakulkan, T.; Oku, S.; Kudo, D.; Nakashimada, Y.; Tajima, T.; Vangnai, A.; Kato, J.
Degradation of chloroanilines by toluene dioxygenase from Pseudomonas putida T57
J. Biosci. Bioeng.
117
292-297
2013
Pseudomonas putida, Pseudomonas putida T57
Manually annotated by BRENDA team
Vila, M.; Umpierrez, D.; Veiga, N.; Seoane, G.; Carrera, I.; Rodriguez Giordano, S.
Site-directed mutagenesis studies on the toluene dioxygenase enzymatic system Role of phenylalanine 366, threonine 365 and isoleucine 324 in the chemo-, regio-, and stereoselectivity
Adv. Synth. Catal.
359
2149-2157
2017
Pseudomonas putida
-
Manually annotated by BRENDA team
Vila, M.A.; Pazos, M.; Iglesias, C.; Veiga, N.; Seoane, G.; Carrera, I.
Toluene dioxygenase-catalysed oxidation of benzyl azide to benzonitrile mechanistic insights for an unprecedented enzymatic transformation
ChemBioChem
17
291-295
2016
Pseudomonas putida
Manually annotated by BRENDA team
Nitisakulkan, T.; Oku, S.; Kudo, D.; Nakashimada, Y.; Tajima, T.; Vangnai, A.; Kato, J.
Degradation of chloroanilines by toluene dioxygenase from Pseudomonas putida T57
J. Biosci. Bioeng.
117
292-297
2014
Pseudomonas putida, Pseudomonas putida T57
Manually annotated by BRENDA team
Vila, M.; Umpierrez, D.; Seoane, G.; Rodriguez, S.; Carrera, I.; Veiga, N.
Computational insights into the oxidation of mono- and 1,4 disubstituted arenes by the toluene dioxygenase enzymatic complex
J. Mol. Catal. B
133
5410-5419
2016
Pseudomonas putida (A5W4F2), Pseudomonas putida strain ATCC 700007 (A5W4F2)
-
Manually annotated by BRENDA team
Hoering, P.; Rothschild-Mancinelli, K.; Sharma, N.; Boyd, D.; Allen, C.
Oxidative biotransformations of phenol substrates catalysed by toluene dioxygenase A molecular docking study
J. Mol. Catal. B
134
396-406
2016
Pseudomonas putida, Pseudomonas putida UV4
-
Manually annotated by BRENDA team
Boyd, D.R.; Sharma, N.D.; Malone, J.F.; McIntyre, P.B.; McRoberts, C.; Floyd, S.; Allen, C.C.; Gohil, A.; Coles, S.J.; Horton, P.N.; Stevenson, P.J.
Toluene dioxygenase-catalyzed synthesis and reactions of cis-diol metabolites derived from 2- and 3-methoxyphenols
J. Org. Chem.
80
3429-3439
2015
Pseudomonas putida, Pseudomonas putida UV4
Manually annotated by BRENDA team
Froese, J.; Endoma-Arias, M.; Hudlicky, T.
Processing of o-halobenzoates by toluene dioxygenase. The role of the alkoxy functionality in the regioselectivity of the enzymatic dihydroxylation reaction
Org. Process Res. Dev.
18
801-809
2014
Pseudomonas putida
-
Manually annotated by BRENDA team