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Toluene 2,3-dioxygenase

natively expressed by: Pseudomonas putida F1

Substrates:

(1aS,7bR)-1a,7b-dihydronaphtho[1,2-b]oxirene-1a-d (1aS,7bR)-1a,7b-dihydronaphtho[1,2-b]oxirene-7b-d (1aS,7bR)-1a,7b-dihydrooxireno[2,3-f]quinoline-1a-d (1aS,7bR)-1a,7b-dihydrooxireno[2,3-f]quinoline-1a,7b-d2 (1aS,7bR)-1a,7b-dihydrooxireno[2,3-f]quinoline-7b-d (1aS,7bR)-1a,7b-dihydrooxireno[2,3-h]quinoline-1a-d (1aS,7bR)-1a,7b-dihydrooxireno[2,3-h]quinoline-7b-d (1E)-1-propen-1-yl-benzene (1R,2S)-1,2-dihydronaphthalene-1-d-1,2-diol (1R,2S)-1,2-dihydronaphthalene-2-d-1,2-diol (1S,2S)-3-methoxycyclohexa-3,5-diene-2-d-1,2-diol (1Z)-1-propen-1-yl-benzene (2-acetoxyethyl)benzene (2-cyanoethyl)benzene (2-isothiocyanatoethyl)benzene-1,3-diene (2-methyl-2-phenyl-1,3-dioxolan-4-yl)methanol (2-thiocyanatoethyl)benzene-1,3-diene (5R,6S)-5,6-dihydroquinoline-5-d-5,6-diol (5R,6S)-5,6-dihydroquinoline-5,6-d2-5,6-diol (5R,6S)-5,6-dihydroquinoline-6-d-5,6-diol (7R,8R)-7,8-dihydroquinoline-7-d-7,8-diol (7R,8R)-7,8-dihydroquinoline-8-d-7,8-diol 1-bromo-2-(2-bromoethyl)benzene 1-bromo-2-iodobenzene 1-bromo-2,3-difluorobenzene 1-bromo-3-(trifluoromethyl)benzene 1-bromo-4-iodobenzene 1-bromopropene 1-chloro-2-iodobenzene 1-chloro-2-methylpropene 1-chloro-4-iodobenzene 1-ethyl-4-methyl benzene 1-Fluoro-2-iodobenzene 1-Fluoro-3-iodobenzene 1-fluoro-4-iodobenzene 1-Iodo-2-methylbenzene 1-iodo-4-(trifluoromethyl)benzene 1-Iodo-4-methylbenzene 1-methyl naphthalene 1-methyl-4-(trifluoromethyl)benzene 1-methylpyridin-2-one 1-phenyl-2-propene 1-Phenylethanone 1-phenylpyrazole 1-phenylpyrrole 1,1-dichloro-1-propene 1,1-dichloroethene 1,2-dihydronaphthalene 1,2,3,4-tetrahydronaphthalene 1,2,4-trimethyl benzene 1,3-cycloheptadiene 1,3-cyclohexadiene 1,3-cyclooctadiene 1,3-cyclopentadiene 1,3-dibromobenzene 1,3,5-cycloheptatriene 1,3,5-trimethylbenzene 1,4 dihydronaphthalene 2-(2-bromomethyl)bromobenzene 2-chloroquinoline 2-chlorostyrene 2-chlorotoluene 2-Ethylpyridine 2-indanone 2-methoxy biphenyl 2-methoxynaphthalene 2-methoxyquinoline 2-methyl indene 2-methyl naphthalene 2-methyl-1,3-benzodithiole 2-methyl-2-phenyl-1,3-dioxolane 2-Methylbenzofuran 2-methylbenzothiophene 2-methylsulfanylthiophene 2-phenyl pyridine 2-Phenyl-1,3-dioxolane 2-phenylsulfanylthiophene 2-phenylthiophene 2-propylpyridine 2-pyridyl methyl sulfide 2-thiophen-2-ylsulfanylthiophene 2,2-Dimethylchromene 2,3-dichloropropene 2,3-dimethoxy biphenyl 2,5-dichlorophenol 2H-chromene 3-bromoquinoline 3-bromothiophene 3-chlorostyrene 3-chlorothiophene 3-Ethylpyridine 3-fluorophenyl methyl sulfide 3-fluorostyrene 3-iodophenol 3-methylbenzothiophene 3-methylstyrene 3-methylthiophene 3-phenyl pyridine 3-phenylthiophene 3-propylpyridine 3,4-dichlorobutene 4-bromophenyl methyl sulfide 4-chlorophenyl methyl sulfide 4-chlorostyrene 4-chlorotoluene 4-Ethylpyridine 4-fluorophenyl methyl sulfide 4-fluorotoluene 4-phenyl pyridine 4-Picoline 4-propylpyridine 4-trifluoromethylphenyl methyl sulfide 5-(propan-2-ylidene)cyclopenta-1,3-diene 5-bromo-1H-indene 5-cyanoindole 5-methylbenzo[b]thiophene 5-nitroindole 5-phenyl-1,3-benzodioxole 6-bromo-1H-indene 6-chloroindole 6-methoxyindole 6-methylfulvene 6,6-diethylfulvene 6,7-dihydro-5H-benzocycloheptene 6,7,8,9-tetrahydro-5H-benzo[7]annulene 7-bromoindole 7-chloroindole 9,10-dihydroanthracene allylbenzoate anisole azulene Benzene benzocyclobutene benzocyclohept-1-ene benzofuran benzonitrile benzothiophene biphenyl Biphenylene bromobenzene chlorobenzene chroman-4-ol chromane cis-1-bromopropene cis-1-chloro-1-propene cis-1,2-dichloroethene cis-1,4-dichloro-2-butene cis-2-chloro-2-butene cis-2-heptene cis-2-hexene cis-2-octene cis-2-pentene cis-dibromoethylene cyclohexene dihydrobenzofuran diphenyl sulfide Diphenylmethane E-beta-bromostyrene ethyl phenyl sulfide ethylbenzene ethylbenzoate ethynylbenzene fluorene furan i-propylbenzoate i-propylphenylsulfide indan indene iodobenzene isopropenylbenzene isopropylbenzene isoquinoline m-nitrotoluene m-xylene methoxylmethyl phenyl sulfide methyl p-nitrophenyl sulfide methyl p-tolyl sulfide methyl phenyl sulfide methylbenzoate methylsulfanylmethylsulfanylbenzene n-butyl-benzene n-butylphenylsulfide n-heptyl-phenyl sulfide n-hexyl-phenyl sulfide n-octyl-phenyl sulfide n-pentyl phenyl sulfide n-propylbenzene n-propylbenzoate n-propylphenylsulfide naphthalene o-bromostyrene o-nitrotoluene p-dichlorobenzene p-methoxyphenyl methyl sulfide p-nitrotoluene p-xylene phenetole phenol phenyl vinyl sulphide phenylmethyl acetate prop-2-yn-1-yl benzoate quinazoline quinoline quinoxaline styrene t-butyl benzene t-butyl phenyl sulfide Toluene trans-1-chloro-1-propene trans-1,4-dichloro-2-butene trans-2-chloro-2-butene trans-2-hexene trans-cinnamonitrile trans-dibromoethylene trichloroethene trifluoromethyl benzene Z-beta-bromostyrene

Compound	Product	Expression System	Reference
(1aS,7bR)-1a,7b-dihydronaphtho[1,2-b]oxirene-1a-d		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
(1aS,7bR)-1a,7b-dihydronaphtho[1,2-b]oxirene-7b-d		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
(1aS,7bR)-1a,7b-dihydrooxireno[2,3-f]quinoline-1a-d		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
(1aS,7bR)-1a,7b-dihydrooxireno[2,3-f]quinoline-1a,7b-d2		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
(1aS,7bR)-1a,7b-dihydrooxireno[2,3-f]quinoline-7b-d		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
(1aS,7bR)-1a,7b-dihydrooxireno[2,3-h]quinoline-1a-d		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
(1aS,7bR)-1a,7b-dihydrooxireno[2,3-h]quinoline-7b-d		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
(1E)-1-propen-1-yl-benzene	(1S,2R)-3-((E)-prop-1-en-1-yl)cyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
(1R,2S)-1,2-dihydronaphthalene-1-d-1,2-diol		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
(1R,2S)-1,2-dihydronaphthalene-2-d-1,2-diol		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
(1S,2S)-3-methoxycyclohexa-3,5-diene-2-d-1,2-diol		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
(1Z)-1-propen-1-yl-benzene	(1S,2R)-3-((Z)-prop-1-en-1-yl)cyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
(2-acetoxyethyl)benzene		Escherichia coli BL21 pDTG601a todC1C2BA	+
Hudlicky, T., Endoma, M. A. A., & Butora, G. (1996). Nucleophilic substitution of protected β-bromoethyl cyclohexadiene-cis-diol as an alternative to direct microbial oxidation of β-functionalized phenethyl substrates. J. Chem. Soc., Perkin Trans. 1, (17), 2187–2192. doi: 10.1039/P19960002187
(2-cyanoethyl)benzene		Escherichia coli BL21 pDTG601a todC1C2BA	+
Hudlicky, T., Endoma, M. A. A., & Butora, G. (1996). Nucleophilic substitution of protected β-bromoethyl cyclohexadiene-cis-diol as an alternative to direct microbial oxidation of β-functionalized phenethyl substrates. J. Chem. Soc., Perkin Trans. 1, (17), 2187–2192. doi: 10.1039/P19960002187
(2-isothiocyanatoethyl)benzene-1,3-diene	(5S,6R)-1-(2-isothiocyanatoethyl)-cis-5,6-dihydroxycyclohexa-1,3-diene	Escherichia coli BL21 pDTG601a todC1C2BA	+
Hudlicky, T., Endoma, M. A. A., & Butora, G. (1996). Nucleophilic substitution of protected β-bromoethyl cyclohexadiene-cis-diol as an alternative to direct microbial oxidation of β-functionalized phenethyl substrates. J. Chem. Soc., Perkin Trans. 1, (17), 2187–2192. doi: 10.1039/P19960002187
(2-methyl-2-phenyl-1,3-dioxolan-4-yl)methanol		Pseudomonas putida F39/D	+
Williams, M., Olson, P., Tautvydas, K., Bitner, R., Mader, R., & Wackett, L. (1990). The application of toluene dioxygenase in the synthesis of acetylene-terminated resins. Applied Microbiology and Biotechnology, 34(3). doi: 10.1007/BF00170050
(2-methyl-2-phenyl-1,3-dioxolan-4-yl)methanol		Pseudomonas putida F39/D	+
Williams, M., Olson, P., Tautvydas, K., Bitner, R., Mader, R., & Wackett, L. (1990). The application of toluene dioxygenase in the synthesis of acetylene-terminated resins. Applied Microbiology and Biotechnology, 34(3). doi: 10.1007/BF00170050
(2-thiocyanatoethyl)benzene-1,3-diene	(5S,6R)-1-(2-thiocyanatoethyl)-cis-5,6-dihydroxycyclohexa-1,3-diene	Escherichia coli BL21 pDTG601a todC1C2BA	+
Hudlicky, T., Endoma, M. A. A., & Butora, G. (1996). Nucleophilic substitution of protected β-bromoethyl cyclohexadiene-cis-diol as an alternative to direct microbial oxidation of β-functionalized phenethyl substrates. J. Chem. Soc., Perkin Trans. 1, (17), 2187–2192. doi: 10.1039/P19960002187
(5R,6S)-5,6-dihydroquinoline-5-d-5,6-diol		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
(5R,6S)-5,6-dihydroquinoline-5,6-d2-5,6-diol		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
(5R,6S)-5,6-dihydroquinoline-6-d-5,6-diol		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
(7R,8R)-7,8-dihydroquinoline-7-d-7,8-diol		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
(7R,8R)-7,8-dihydroquinoline-8-d-7,8-diol		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
1-bromo-2-(2-bromoethyl)benzene		Pseudomonas putida F39/D	+
Stabile, M. R., Hudlicky, T., Meisels, M. L., Butora, G., Gum, A. G., Fearnley, S. P., … Ellis, M. R. (1995). Oxidation of 2-(2-bromoethyl)bromobenzene with toluene dioxygenase: Isolation and identification of new chiral synthons. Chirality, 7(7), 556–559. doi: 10.1002/chir.530070710
1-bromo-2-iodobenzene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Barr, S. A., Dalton, H., Chima, J., Whited, G., & Seemayer, R. (1994). Chemoenzymic Synthesis of the 2,3- and 3,4-cis-Dihydrodiol Enantiomers of Monosubstituted Benzenes. Journal of the American Chemical Society, 116(3), 1147–1148. doi: 10.1021/ja00082a053
1-bromo-2,3-difluorobenzene	1-bromo-5,6-difluoro-cis-2,3-dihydroxycyclohexa-4,6-diene	Pseudomonas putida F1	+
Hudlicky, T., Gonzalez, D., Stabile, M., Endoma, M. A. A., Deluca, M., Parker, D., … Whited, G. M. (1998). New metabolites from the microbial oxidation of fluorinated aromatic compounds. Journal of Fluorine Chemistry, 89(1), 23–30. doi: 10.1016/S0022-1139(98)00081-5
1-bromo-2,3-difluorobenzene	1-bromo-5,6-difluoro-cis-2,3-dihydroxycyclohexa-4,6-diene	Escherichia coli BL21 pDTG601 todC1C2BA	+
Hudlicky, T., Gonzalez, D., Stabile, M., Endoma, M. A. A., Deluca, M., Parker, D., … Whited, G. M. (1998). New metabolites from the microbial oxidation of fluorinated aromatic compounds. Journal of Fluorine Chemistry, 89(1), 23–30. doi: 10.1016/S0022-1139(98)00081-5
1-bromo-3-(trifluoromethyl)benzene	3-trifluoromethyl-5-bromo-cis-1,2-dihydroxycyclohexa-3,5-diene	Pseudomonas putida F1	+
Hudlicky, T., Gonzalez, D., Stabile, M., Endoma, M. A. A., Deluca, M., Parker, D., … Whited, G. M. (1998). New metabolites from the microbial oxidation of fluorinated aromatic compounds. Journal of Fluorine Chemistry, 89(1), 23–30. doi: 10.1016/S0022-1139(98)00081-5
1-bromo-3-(trifluoromethyl)benzene	3-bromo-5-trifluoromethyl-cis-1,2-dihydroxycyclohexa-3,5-diene	Pseudomonas putida F1	+
Hudlicky, T., Gonzalez, D., Stabile, M., Endoma, M. A. A., Deluca, M., Parker, D., … Whited, G. M. (1998). New metabolites from the microbial oxidation of fluorinated aromatic compounds. Journal of Fluorine Chemistry, 89(1), 23–30. doi: 10.1016/S0022-1139(98)00081-5
1-bromo-3-(trifluoromethyl)benzene	3-trifluoromethyl-5-bromo-cis-1,2-dihydroxycyclohexa-3,5-diene	Escherichia coli BL21 pDTG601 todC1C2BA	+
Hudlicky, T., Gonzalez, D., Stabile, M., Endoma, M. A. A., Deluca, M., Parker, D., … Whited, G. M. (1998). New metabolites from the microbial oxidation of fluorinated aromatic compounds. Journal of Fluorine Chemistry, 89(1), 23–30. doi: 10.1016/S0022-1139(98)00081-5
1-bromo-3-(trifluoromethyl)benzene	3-bromo-5-trifluoromethyl-cis-1,2-dihydroxycyclohexa-3,5-diene	Escherichia coli BL21 pDTG601 todC1C2BA	+
Hudlicky, T., Gonzalez, D., Stabile, M., Endoma, M. A. A., Deluca, M., Parker, D., … Whited, G. M. (1998). New metabolites from the microbial oxidation of fluorinated aromatic compounds. Journal of Fluorine Chemistry, 89(1), 23–30. doi: 10.1016/S0022-1139(98)00081-5
1-bromo-3-(trifluoromethyl)benzene		Pseudomonas putida F39/D	+
Hudlicky, T., Gonzalez, D., Stabile, M., Endoma, M. A. A., Deluca, M., Parker, D., … Whited, G. M. (1998). New metabolites from the microbial oxidation of fluorinated aromatic compounds. Journal of Fluorine Chemistry, 89(1), 23–30. doi: 10.1016/S0022-1139(98)00081-5
1-bromo-4-iodobenzene	1-bromo-4-iodo-cis-2,3-dihydroxycyclohexa-4,6-diene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Hand, M. V., Groocock, M. R., Kerley, N. A., Dalton, H., … Sheldrake, G. N. (1993). Stereodirecting substituent effects during enzyme-catalysed synthesis of cis-dihydrodiol metabolites of 1,4-disubstituted benzene substrates. Journal of the Chemical Society, Chemical Communications, (11), 974. doi: 10.1039/C39930000974
1-bromopropene		Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
1-chloro-2-iodobenzene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Barr, S. A., Dalton, H., Chima, J., Whited, G., & Seemayer, R. (1994). Chemoenzymic Synthesis of the 2,3- and 3,4-cis-Dihydrodiol Enantiomers of Monosubstituted Benzenes. Journal of the American Chemical Society, 116(3), 1147–1148. doi: 10.1021/ja00082a053
1-chloro-2-methylpropene	3-Chloro-2-methyl-2-propene- 1-ol	Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
1-chloro-4-iodobenzene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Hand, M. V., Groocock, M. R., Kerley, N. A., Dalton, H., … Sheldrake, G. N. (1993). Stereodirecting substituent effects during enzyme-catalysed synthesis of cis-dihydrodiol metabolites of 1,4-disubstituted benzene substrates. Journal of the Chemical Society, Chemical Communications, (11), 974. doi: 10.1039/C39930000974
1-ethyl-4-methyl benzene		Pseudomonas putida F1	+
Gibson DT, Gschwendt B, Yeh WK, Kobal VM. Initial reactions in the oxidation of ethylbenzene by Pseudomonas putida. Biochemistry. 1973 Apr 10;12(8):1520-8. PMID: 4699984
1-ethyl-4-methyl benzene		Pseudomonas putida F39/D	+
Gibson DT, Gschwendt B, Yeh WK, Kobal VM. Initial reactions in the oxidation of ethylbenzene by Pseudomonas putida. Biochemistry. 1973 Apr 10;12(8):1520-8. PMID: 4699984
1-Fluoro-2-iodobenzene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Barr, S. A., Dalton, H., Chima, J., Whited, G., & Seemayer, R. (1994). Chemoenzymic Synthesis of the 2,3- and 3,4-cis-Dihydrodiol Enantiomers of Monosubstituted Benzenes. Journal of the American Chemical Society, 116(3), 1147–1148. doi: 10.1021/ja00082a053
1-Fluoro-3-iodobenzene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Barr, S. A., Dalton, H., Chima, J., Whited, G., & Seemayer, R. (1994). Chemoenzymic Synthesis of the 2,3- and 3,4-cis-Dihydrodiol Enantiomers of Monosubstituted Benzenes. Journal of the American Chemical Society, 116(3), 1147–1148. doi: 10.1021/ja00082a053
1-fluoro-4-iodobenzene	1-fluoro-4-iodo-cis-2,3-dihydroxycyclohexa-4,6-diene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Barr, S. A., Dalton, H., Chima, J., Whited, G., & Seemayer, R. (1994). Chemoenzymic Synthesis of the 2,3- and 3,4-cis-Dihydrodiol Enantiomers of Monosubstituted Benzenes. Journal of the American Chemical Society, 116(3), 1147–1148. doi: 10.1021/ja00082a053
1-Iodo-2-methylbenzene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Barr, S. A., Dalton, H., Chima, J., Whited, G., & Seemayer, R. (1994). Chemoenzymic Synthesis of the 2,3- and 3,4-cis-Dihydrodiol Enantiomers of Monosubstituted Benzenes. Journal of the American Chemical Society, 116(3), 1147–1148. doi: 10.1021/ja00082a053
1-Iodo-2-methylbenzene	3-iodo-4-methyl-cis-1,2-dihydroxycyclohexa-3,5-diene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Barr, S. A., Dalton, H., Chima, J., Whited, G., & Seemayer, R. (1994). Chemoenzymic Synthesis of the 2,3- and 3,4-cis-Dihydrodiol Enantiomers of Monosubstituted Benzenes. Journal of the American Chemical Society, 116(3), 1147–1148. doi: 10.1021/ja00082a053
1-iodo-4-(trifluoromethyl)benzene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Hand, M. V., Groocock, M. R., Kerley, N. A., Dalton, H., … Sheldrake, G. N. (1993). Stereodirecting substituent effects during enzyme-catalysed synthesis of cis-dihydrodiol metabolites of 1,4-disubstituted benzene substrates. Journal of the Chemical Society, Chemical Communications, (11), 974. doi: 10.1039/C39930000974
1-Iodo-4-methylbenzene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Hand, M. V., Groocock, M. R., Kerley, N. A., Dalton, H., … Sheldrake, G. N. (1993). Stereodirecting substituent effects during enzyme-catalysed synthesis of cis-dihydrodiol metabolites of 1,4-disubstituted benzene substrates. Journal of the Chemical Society, Chemical Communications, (11), 974. doi: 10.1039/C39930000974
1-Iodo-4-methylbenzene	3-iodo-6-methyl-cis-1,2-dihydroxycyclohexa-3,5-diene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Barr, S. A., Dalton, H., Chima, J., Whited, G., & Seemayer, R. (1994). Chemoenzymic Synthesis of the 2,3- and 3,4-cis-Dihydrodiol Enantiomers of Monosubstituted Benzenes. Journal of the American Chemical Society, 116(3), 1147–1148. doi: 10.1021/ja00082a053
1-methyl naphthalene		Pseudomonas putida F39/D	+
Deluca, M. E., & Hudlicky, T. (1990). Microbial oxidation of naphthalene derivatives. Absolute configuration of metabolites. Tetrahedron Letters, 31(1), 13–16. doi: 10.1016/S0040-4039(00)94321-1
1-methyl-4-(trifluoromethyl)benzene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Hand, M. V., Groocock, M. R., Kerley, N. A., Dalton, H., … Sheldrake, G. N. (1993). Stereodirecting substituent effects during enzyme-catalysed synthesis of cis-dihydrodiol metabolites of 1,4-disubstituted benzene substrates. Journal of the Chemical Society, Chemical Communications, (11), 974. doi: 10.1039/C39930000974
1-methylpyridin-2-one	cis-3,4-dihydro-3,4-dihydroxy-1-methyl-2-pyridone	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Modyanova, L. V., Carroll, J. G., Malone, J. F., Allen, C. C., … Dalton, H. (2002). Dioxygenase-catalyzed cis -dihydroxylation of pyridine-ring systems . Canadian Journal of Chemistry, 80(6), 589–600. doi: 10.1139/v02-062
1-phenyl-2-propene	(1S,2R)-3-prop-2-enylcyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
1-Phenylethanone	3-acetyl-cis-1,2-dihydroxycyclohexa-3,5-diene	Pseudomonas putida F39/D	+
Gibson DT, Gschwendt B, Yeh WK, Kobal VM. Initial reactions in the oxidation of ethylbenzene by Pseudomonas putida. Biochemistry. 1973 Apr 10;12(8):1520-8. PMID: 4699984
1-phenylpyrazole	(1S,2R)-3-(1H-pyrazol-1-yl)cyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Coen GP, Hempenstall F, Ljubez V, Malone JF, Allen CC, Hamilton JT. Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates. Org Biomol Chem. 2008 Nov 7;6(21):3957-66. doi: 10.1039/b810235j. PMID: 18931802
1-phenylpyrrole	(1S,2R)-3-(1H-pyrrol-1-yl)cyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Coen GP, Hempenstall F, Ljubez V, Malone JF, Allen CC, Hamilton JT. Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates. Org Biomol Chem. 2008 Nov 7;6(21):3957-66. doi: 10.1039/b810235j. PMID: 18931802
1,1-dichloro-1-propene	3,3-Dichloro-2-propene-1-ol	Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
1,1-dichloroethene		Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
1,2-dihydronaphthalene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Boyle, R., Evans, T. A., Malone, J. F., McCombe, K. M., … Chima, J. (1996). Chemical and enzyme-catalysed syntheses of enantiopure epoxide and diol derivatives of chromene, 2,2-dimethylchromene, and 7-methoxy-2,2-dimethylchromene (precocene-1). Journal of the Chemical Society, Perkin Transactions 1, (14), 1757. doi: 10.1039/P19960001757
1,2,3,4-tetrahydronaphthalene	(1R)-1,2,3,4-tetrahydronaphthalen-1-ol	Pseudomonas putida UV4	+
Derek R., B., Narain D., S., Paul J., S., Jagdeep, C., David J., G., & Howard, D. (1991). Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites. Tetrahedron Letters, 32(31), 3887–3890. doi: 10.1016/S0040-4039(00)79405-6
1,2,3,4-tetrahydronaphthalene	alpha-tetralone	Pseudomonas putida UV4	+
Derek R., B., Narain D., S., Paul J., S., Jagdeep, C., David J., G., & Howard, D. (1991). Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites. Tetrahedron Letters, 32(31), 3887–3890. doi: 10.1016/S0040-4039(00)79405-6
1,2,4-trimethyl benzene		Pseudomonas putida F1	+
Leahy JG, Tracy KD, Eley MH. Degradation of mixtures of aromatic and chloroaliphatic hydrocarbons by aromatic hydrocarbon-degrading bacteria. FEMS Microbiol Ecol. 2003 Mar 1;43(2):271-6. doi: 10.1111/j.1574-6941.2003.tb01067.x. PMID: 19719688
1,3-cycloheptadiene	(1R,2S)-cyclohept-3-ene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
1,3-cyclohexadiene	(1R,2S)-cyclohex-3-ene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
1,3-cyclooctadiene	(1R,2S,Z)-cyclooct-3-ene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
1,3-cyclopentadiene	(1R,2S)-cyclopent-3-ene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
1,3-dibromobenzene	1,5-dibromo-cis-2,3-dihydroxycyclohexa-4,6-diene	Escherichia coli BL21 pDTG601a todC1C2BA	+
Gonzalez, D., Martinot, T., & Hudlicky, T. (1999). A short chemoenzymatic synthesis of (+)-narciclasine. Tetrahedron Letters, 40(16), 3077–3080. doi: 10.1016/S0040-4039(99)00433-5
1,3,5-cycloheptatriene	(1R,2S)-cyclohepta-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Bowers, N. I., Boyd, D. R., Sharma, N. D., Kennedy, M. A., Sheldrake, G. N., & Dalton, H. (1998). Stereoselective cis-dihydroxylation of azulene and related non-aromatic polyenes. Tetrahedron: Asymmetry, 9(11), 1831–1834. doi: 10.1016/S0957-4166(98)00161-X
1,3,5-cycloheptatriene	(1R,2S)-cyclohepta-3,6-diene-1,2-diol	Pseudomonas putida UV4	+
Bowers, N. I., Boyd, D. R., Sharma, N. D., Kennedy, M. A., Sheldrake, G. N., & Dalton, H. (1998). Stereoselective cis-dihydroxylation of azulene and related non-aromatic polyenes. Tetrahedron: Asymmetry, 9(11), 1831–1834. doi: 10.1016/S0957-4166(98)00161-X
1,3,5-trimethylbenzene		Pseudomonas putida F1	+
Leahy JG, Tracy KD, Eley MH. Degradation of mixtures of aromatic and chloroaliphatic hydrocarbons by aromatic hydrocarbon-degrading bacteria. FEMS Microbiol Ecol. 2003 Mar 1;43(2):271-6. doi: 10.1111/j.1574-6941.2003.tb01067.x. PMID: 19719688
1,4 dihydronaphthalene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Boyle, R., Evans, T. A., Malone, J. F., McCombe, K. M., … Chima, J. (1996). Chemical and enzyme-catalysed syntheses of enantiopure epoxide and diol derivatives of chromene, 2,2-dimethylchromene, and 7-methoxy-2,2-dimethylchromene (precocene-1). Journal of the Chemical Society, Perkin Transactions 1, (14), 1757. doi: 10.1039/P19960001757
1,4 dihydronaphthalene	cis-1,2,3,4-tetrahydronaphthalene-2,3-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
2-(2-bromomethyl)bromobenzene	4-bromo-3-(bromomethyl)cyclohexa-3,5-diene-1,2-diol	Pseudomonas putida F39/D	+
Stabile, M. R., Hudlicky, T., Meisels, M. L., Butora, G., Gum, A. G., Fearnley, S. P., … Ellis, M. R. (1995). Oxidation of 2-(2-bromoethyl)bromobenzene with toluene dioxygenase: Isolation and identification of new chiral synthons. Chirality, 7(7), 556–559. doi: 10.1002/chir.530070710
2-chloroquinoline		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Modyanova, L. V., Carroll, J. G., Malone, J. F., Allen, C. C., … Dalton, H. (2002). Dioxygenase-catalyzed cis -dihydroxylation of pyridine-ring systems . Canadian Journal of Chemistry, 80(6), 589–600. doi: 10.1139/v02-062
2-chlorostyrene		Pseudomonas putida F39/D	+
Hudlicky, T., Boros, E. E., & Boros, C. H. (1993). New diol metabolites derived by biooxidation of chlorostyrenes with Pseudomonas putida: Determination of absolute stereochemistry and enantiomeric excess by convergent syntheses. Tetrahedron: Asymmetry, 4(6), 1365–1386. doi: 10.1016/S0957-4166(00)80247-5
2-chlorotoluene		Pseudomonas putida F1	+
Leahy JG, Tracy KD, Eley MH. Degradation of mixtures of aromatic and chloroaliphatic hydrocarbons by aromatic hydrocarbon-degrading bacteria. FEMS Microbiol Ecol. 2003 Mar 1;43(2):271-6. doi: 10.1111/j.1574-6941.2003.tb01067.x. PMID: 19719688
2-Ethylpyridine	(R)-1-(2-pyridyl)ethanol	Pseudomonas putida UV4	+
Garrett, M. D., Scott, R., & Sheldrake, G. N. (2002). Enantiocomplementary preparation of (S)- and (R)-1-pyridylalkanols via ketone reduction and alkane hydroxylation using whole cells of Pseudomonas putida UV4. Tetrahedron: Asymmetry, 13(20), 2201–2204. doi: 10.1016/S0957-4166(02)00634-1
2-indanone	(S)-2-Hydroxy-1-indanone	Pseudomonas putida F39/D	+
Resnick SM, Torok DS, Lee K, Brand JM, Gibson DT. Regiospecific and stereoselective hydroxylation of 1-indanone and 2-indanone by naphthalene dioxygenase and toluene dioxygenase. Appl Environ Microbiol. 1994 Sep;60(9):3323-8. Erratum in: Appl Environ Microbiol 1995 Feb;61(2):847. PubMed Central PMCID: PMC201805. PMID: 7944365
2-methoxy biphenyl		Escherichia coli BL21 pDTG601a todC1C2BA	+
Gonzalez, D., Schapiro, V., Seoane, G., & Hudlicky, T. (1997). New metabolites from toluene dioxygenase dihydroxylation of oxygenated biphenyls. Tetrahedron: Asymmetry, 8(7), 975–977. doi: 10.1016/S0957-4166(97)00059-1
2-methoxynaphthalene		Pseudomonas putida F39/D	+
Whited GM, Downie JC, Hudlicky T, Fearnley SP, Dudding TC, Olivo HF, Parker D. Oxidation of 2-methoxynaphthalene by toluene, naphthalene and biphenyl dioxygenases:structure and absolute stereochemistry of metabolites. Bioorg Med Chem. 1994 Jul;2(7):727-34. PMID: 7858982
2-methoxyquinoline		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Modyanova, L. V., Carroll, J. G., Malone, J. F., Allen, C. C., … Dalton, H. (2002). Dioxygenase-catalyzed cis -dihydroxylation of pyridine-ring systems . Canadian Journal of Chemistry, 80(6), 589–600. doi: 10.1139/v02-062
2-methyl indene	(1S,2R)-2,3-dihydro-2-methyl-1H-Indene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
2-methyl indene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
2-methyl indene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
2-methyl naphthalene		Pseudomonas putida F39/D	+
Deluca, M. E., & Hudlicky, T. (1990). Microbial oxidation of naphthalene derivatives. Absolute configuration of metabolites. Tetrahedron Letters, 31(1), 13–16. doi: 10.1016/S0040-4039(00)94321-1
2-methyl-1,3-benzodithiole		Pseudomonas putida UV4	+
Alien, C. C. R., Boyd, D. R., Dalton, H., Sharma, N. D., Haughey, S. A., McMordie, R. A. S., … Sproule, K. (1995). Sulfoxides of high enantiopurity from bacterial dioxygenase-catalysed oxidation. Journal of the Chemical Society, Chemical Communications, (2), 119. doi: 10.1039/C39950000119
2-methyl-1,3-benzodithiole		Pseudomonas putida UV4	+
Alien, C. C. R., Boyd, D. R., Dalton, H., Sharma, N. D., Haughey, S. A., McMordie, R. A. S., … Sproule, K. (1995). Sulfoxides of high enantiopurity from bacterial dioxygenase-catalysed oxidation. Journal of the Chemical Society, Chemical Communications, (2), 119. doi: 10.1039/C39950000119
2-methyl-2-phenyl-1,3-dioxolane	(1S,2R)-3-(2-methyl-1,3-dioxolan-2-yl)cyclohexa-3,5-diene-1,2-diol	Pseudomonas putida F39/D	+
Williams, M., Olson, P., Tautvydas, K., Bitner, R., Mader, R., & Wackett, L. (1990). The application of toluene dioxygenase in the synthesis of acetylene-terminated resins. Applied Microbiology and Biotechnology, 34(3). doi: 10.1007/BF00170050
2-Methylbenzofuran		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Brannigan, I. N., Haughey, S. A., Malone, J. F., Clarke, D. A., & Dalton, H. (1996). Dioxygenase-catalysed formation of cis/trans-dihydrodiol metabolites of mono- and bi-cyclic heteroarenes. Chemical Communications, (20), 2361. doi: 10.1039/CC9960002361
2-methylbenzothiophene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Haughey, S. A., Malone, J. F., McMurray, B. T., Sheldrake, G. N., … Dalton, H. (1996). Enantioselective dioxygenase-catalysed formation and thermal racemisation of chiral thiophene sulfoxides. Chemical Communications, (20), 2363. doi: 10.1039/CC9960002363
2-methylsulfanylthiophene	(+)-(R)-2-thienyl methyl sulfoxide	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Gunaratne, N., Haughey, S. A., Kennedy, M. A., Malone, J. F., … Dalton, H. (2003). Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. Organic & Biomolecular Chemistry, 1(6), 984–994. doi: 10.1039/B300867N
2-methylsulfanylthiophene	(+)-(R)-2-thienyl methyl sulfoxide	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
2-phenyl pyridine		Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Coen GP, Hempenstall F, Ljubez V, Malone JF, Allen CC, Hamilton JT. Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates. Org Biomol Chem. 2008 Nov 7;6(21):3957-66. doi: 10.1039/b810235j. PMID: 18931802
2-Phenyl-1,3-dioxolane	(1S,2R)-3-(1,3-dioxolan-2-yl)cyclohexa-3,5-diene-1,2-diol	Pseudomonas putida F39/D	+
Williams, M., Olson, P., Tautvydas, K., Bitner, R., Mader, R., & Wackett, L. (1990). The application of toluene dioxygenase in the synthesis of acetylene-terminated resins. Applied Microbiology and Biotechnology, 34(3). doi: 10.1007/BF00170050
2-phenylsulfanylthiophene	(+)-2-phenylsulfinylthiophene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Gunaratne, N., Haughey, S. A., Kennedy, M. A., Malone, J. F., … Dalton, H. (2003). Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. Organic & Biomolecular Chemistry, 1(6), 984–994. doi: 10.1039/B300867N
2-phenylthiophene	(+)-(1S,2R)-1,2-Dihydroxy-3-(2-thienyl)-cyclohexa-3,5-diene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Gunaratne, N., Haughey, S. A., Kennedy, M. A., Malone, J. F., … Dalton, H. (2003). Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. Organic & Biomolecular Chemistry, 1(6), 984–994. doi: 10.1039/B300867N
2-phenylthiophene	2-(2'-hydroxyphenyl)-thiophene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Gunaratne, N., Haughey, S. A., Kennedy, M. A., Malone, J. F., … Dalton, H. (2003). Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. Organic & Biomolecular Chemistry, 1(6), 984–994. doi: 10.1039/B300867N
2-phenylthiophene	2-(3'-hydroxyphenyl)thiophene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Gunaratne, N., Haughey, S. A., Kennedy, M. A., Malone, J. F., … Dalton, H. (2003). Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. Organic & Biomolecular Chemistry, 1(6), 984–994. doi: 10.1039/B300867N
2-propylpyridine	(R)-1-(2-pyridyl)propanol	Pseudomonas putida UV4	+
Garrett, M. D., Scott, R., & Sheldrake, G. N. (2002). Enantiocomplementary preparation of (S)- and (R)-1-pyridylalkanols via ketone reduction and alkane hydroxylation using whole cells of Pseudomonas putida UV4. Tetrahedron: Asymmetry, 13(20), 2201–2204. doi: 10.1016/S0957-4166(02)00634-1
2-pyridyl methyl sulfide	2-pyridyl methylsulfoxide	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
2-thiophen-2-ylsulfanylthiophene	2-thiophen-2-ylsulfinylthiophene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Gunaratne, N., Haughey, S. A., Kennedy, M. A., Malone, J. F., … Dalton, H. (2003). Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. Organic & Biomolecular Chemistry, 1(6), 984–994. doi: 10.1039/B300867N
2,2-Dimethylchromene	cis-3,4-dihydroxy-2,2-dimethylchromane	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Boyle, R., Evans, T. A., Malone, J. F., McCombe, K. M., … Chima, J. (1996). Chemical and enzyme-catalysed syntheses of enantiopure epoxide and diol derivatives of chromene, 2,2-dimethylchromene, and 7-methoxy-2,2-dimethylchromene (precocene-1). Journal of the Chemical Society, Perkin Transactions 1, (14), 1757. doi: 10.1039/P19960001757
2,3-dichloropropene	2,3-Dichloro-2-propene-1-ol	Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
2,3-dimethoxy biphenyl		Escherichia coli BL21 pDTG601a todC1C2BA	+
Gonzalez, D., Schapiro, V., Seoane, G., & Hudlicky, T. (1997). New metabolites from toluene dioxygenase dihydroxylation of oxygenated biphenyls. Tetrahedron: Asymmetry, 8(7), 975–977. doi: 10.1016/S0957-4166(97)00059-1
2,5-dichlorophenol	3,6-dichlorocatechol	Pseudomonas putida F1	+
Spain JC, Zylstra GJ, Blake CK, Gibson DT. Monohydroxylation of phenol and 2,5-dichlorophenol by toluene dioxygenase in Pseudomonas putida F1. Appl Environ Microbiol. 1989 Oct;55(10):2648-52. Erratum in: Appl Environ Microbiol 1991 May;57(5):1579. PubMed Central PMCID: PMC203138. PMID: 2604403
2H-chromene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Boyle, R., Evans, T. A., Malone, J. F., McCombe, K. M., … Chima, J. (1996). Chemical and enzyme-catalysed syntheses of enantiopure epoxide and diol derivatives of chromene, 2,2-dimethylchromene, and 7-methoxy-2,2-dimethylchromene (precocene-1). Journal of the Chemical Society, Perkin Transactions 1, (14), 1757. doi: 10.1039/P19960001757
2H-chromene	chromen-2-one	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Boyle, R., Evans, T. A., Malone, J. F., McCombe, K. M., … Chima, J. (1996). Chemical and enzyme-catalysed syntheses of enantiopure epoxide and diol derivatives of chromene, 2,2-dimethylchromene, and 7-methoxy-2,2-dimethylchromene (precocene-1). Journal of the Chemical Society, Perkin Transactions 1, (14), 1757. doi: 10.1039/P19960001757
2H-chromene	3-(2-hydroxyphenyl)-2-propenal	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Boyle, R., Evans, T. A., Malone, J. F., McCombe, K. M., … Chima, J. (1996). Chemical and enzyme-catalysed syntheses of enantiopure epoxide and diol derivatives of chromene, 2,2-dimethylchromene, and 7-methoxy-2,2-dimethylchromene (precocene-1). Journal of the Chemical Society, Perkin Transactions 1, (14), 1757. doi: 10.1039/P19960001757
3-bromoquinoline		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Modyanova, L. V., Carroll, J. G., Malone, J. F., Allen, C. C., … Dalton, H. (2002). Dioxygenase-catalyzed cis -dihydroxylation of pyridine-ring systems . Canadian Journal of Chemistry, 80(6), 589–600. doi: 10.1139/v02-062
3-bromothiophene	cis-4-bromo-2,3-dihydroxy-2,3-dihydro-thiophene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Gunaratne, N., Haughey, S. A., Kennedy, M. A., Malone, J. F., … Dalton, H. (2003). Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. Organic & Biomolecular Chemistry, 1(6), 984–994. doi: 10.1039/B300867N
3-bromothiophene	trans-4-bromo-2,3-dihydroxy-2,3-dihydro-thiophene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Gunaratne, N., Haughey, S. A., Kennedy, M. A., Malone, J. F., … Dalton, H. (2003). Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. Organic & Biomolecular Chemistry, 1(6), 984–994. doi: 10.1039/B300867N
3-chlorostyrene	(1S)-1-(3-chlorophenyl)-1,2-ethanediol	Pseudomonas putida F39/D	+
Hudlicky, T., Boros, E. E., & Boros, C. H. (1993). New diol metabolites derived by biooxidation of chlorostyrenes with Pseudomonas putida: Determination of absolute stereochemistry and enantiomeric excess by convergent syntheses. Tetrahedron: Asymmetry, 4(6), 1365–1386. doi: 10.1016/S0957-4166(00)80247-5
3-chlorostyrene	cis-1-chloro-5-vinylcyclohexa-4,6-diene-2,3-diol	Pseudomonas putida F39/D	+
Hudlicky, T., Boros, E. E., & Boros, C. H. (1993). New diol metabolites derived by biooxidation of chlorostyrenes with Pseudomonas putida: Determination of absolute stereochemistry and enantiomeric excess by convergent syntheses. Tetrahedron: Asymmetry, 4(6), 1365–1386. doi: 10.1016/S0957-4166(00)80247-5
3-chlorostyrene	(2R,3S)-cis-5-chloro-1-vinylcyclohexa-4,6-diene-2,3-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
3-chlorostyrene	(S)-1-(3-chlorophenyl)propan-1-ol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
3-chlorothiophene	cis-4-chloro-2,3-dihydroxy-2,3-dihydro-thiophene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Gunaratne, N., Haughey, S. A., Kennedy, M. A., Malone, J. F., … Dalton, H. (2003). Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. Organic & Biomolecular Chemistry, 1(6), 984–994. doi: 10.1039/B300867N
3-chlorothiophene	trans-4-chloro-2,3-dihydroxy-2,3-dihydro-thiophene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Gunaratne, N., Haughey, S. A., Kennedy, M. A., Malone, J. F., … Dalton, H. (2003). Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. Organic & Biomolecular Chemistry, 1(6), 984–994. doi: 10.1039/B300867N
3-Ethylpyridine	(R)-1-(3-pyridyl)ethanol	Pseudomonas putida UV4	+
Garrett, M. D., Scott, R., & Sheldrake, G. N. (2002). Enantiocomplementary preparation of (S)- and (R)-1-pyridylalkanols via ketone reduction and alkane hydroxylation using whole cells of Pseudomonas putida UV4. Tetrahedron: Asymmetry, 13(20), 2201–2204. doi: 10.1016/S0957-4166(02)00634-1
3-fluorophenyl methyl sulfide	3-fluorophenyl methyl sulfoxide	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
3-fluorostyrene	(1S,2R)-5-fluoro-3-vinylcyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
3-fluorostyrene	(S)-1-(3-fluorophenyl)propan-1-ol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
3-iodophenol		Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Ljubez V, McGeehin PK, Stevenson PJ, Blain M, Allen CC. Chemoenzymatic synthesis of monocyclic arene oxides and arene hydrates from substituted benzene substrates. Org Biomol Chem. 2013 May 14;11(18):3020-9. doi: 10.1039/c3ob40166a. PMID: 23532167
3-methylbenzothiophene	(2S,3R)-3-methyl-2,3-dihydrobenzo[b]thiophene-2,3-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Haughey, S. A., Malone, J. F., McMurray, B. T., Sheldrake, G. N., … Dalton, H. (1996). Enantioselective dioxygenase-catalysed formation and thermal racemisation of chiral thiophene sulfoxides. Chemical Communications, (20), 2363. doi: 10.1039/CC9960002363
3-methylbenzothiophene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Haughey, S. A., Malone, J. F., McMurray, B. T., Sheldrake, G. N., … Dalton, H. (1996). Enantioselective dioxygenase-catalysed formation and thermal racemisation of chiral thiophene sulfoxides. Chemical Communications, (20), 2363. doi: 10.1039/CC9960002363
3-methylstyrene	(1S,2R)-5-methyl-3-vinylcyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
3-methylstyrene	(S)-1-(m-tolyl)propan-1-ol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
3-methylthiophene	cis-4-methyl-2,3-dihydroxy-2,3-dihydrothiophene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Brannigan, I. N., Haughey, S. A., Malone, J. F., Clarke, D. A., & Dalton, H. (1996). Dioxygenase-catalysed formation of cis/trans-dihydrodiol metabolites of mono- and bi-cyclic heteroarenes. Chemical Communications, (20), 2361. doi: 10.1039/CC9960002361
3-methylthiophene	trans-4-methyl-2,3-dihydroxy-2,3-dihydrothiophene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Brannigan, I. N., Haughey, S. A., Malone, J. F., Clarke, D. A., & Dalton, H. (1996). Dioxygenase-catalysed formation of cis/trans-dihydrodiol metabolites of mono- and bi-cyclic heteroarenes. Chemical Communications, (20), 2361. doi: 10.1039/CC9960002361
3-methylthiophene	3-hydroxy-4-methyl-5H-thiophen-2-one	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Brannigan, I. N., Haughey, S. A., Malone, J. F., Clarke, D. A., & Dalton, H. (1996). Dioxygenase-catalysed formation of cis/trans-dihydrodiol metabolites of mono- and bi-cyclic heteroarenes. Chemical Communications, (20), 2361. doi: 10.1039/CC9960002361
3-phenyl pyridine		Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Coen GP, Hempenstall F, Ljubez V, Malone JF, Allen CC, Hamilton JT. Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates. Org Biomol Chem. 2008 Nov 7;6(21):3957-66. doi: 10.1039/b810235j. PMID: 18931802
3-phenylthiophene	cis-4-phenyl-2,3-dihydroxy-2,3-dihydro-thiophene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Gunaratne, N., Haughey, S. A., Kennedy, M. A., Malone, J. F., … Dalton, H. (2003). Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. Organic & Biomolecular Chemistry, 1(6), 984–994. doi: 10.1039/B300867N
3-phenylthiophene	trans-4-phenyl-2,3-dihydroxy-2,3-dihydro-thiophene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Gunaratne, N., Haughey, S. A., Kennedy, M. A., Malone, J. F., … Dalton, H. (2003). Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. Organic & Biomolecular Chemistry, 1(6), 984–994. doi: 10.1039/B300867N
3-phenylthiophene	1,2-dihydroxy-3-(3-thienyl)-cyclohexa-3,5-diene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Gunaratne, N., Haughey, S. A., Kennedy, M. A., Malone, J. F., … Dalton, H. (2003). Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. Organic & Biomolecular Chemistry, 1(6), 984–994. doi: 10.1039/B300867N
3-propylpyridine	(R)-1-(3-pyridyl)propanol	Pseudomonas putida UV4	+
Garrett, M. D., Scott, R., & Sheldrake, G. N. (2002). Enantiocomplementary preparation of (S)- and (R)-1-pyridylalkanols via ketone reduction and alkane hydroxylation using whole cells of Pseudomonas putida UV4. Tetrahedron: Asymmetry, 13(20), 2201–2204. doi: 10.1016/S0957-4166(02)00634-1
3,4-dichlorobutene	3,4-Dichlorobutane-1,2-diol	Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
4-bromophenyl methyl sulfide	1-bromo-4-methylsulfinylbenzene	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
4-bromophenyl methyl sulfide	(1S,2R)-3-bromo-6-methylsulfanylcyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
4-chlorophenyl methyl sulfide	1-chloro-4-methylsulfinylbenzene	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
4-chlorophenyl methyl sulfide	(1S,2R)-3-chloro-6-methylsulfanylcyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
4-chlorostyrene	(1R)-1-(4-chlorophenyl)-1,2-ethanediol	Pseudomonas putida F39/D	+
Hudlicky, T., Boros, E. E., & Boros, C. H. (1993). New diol metabolites derived by biooxidation of chlorostyrenes with Pseudomonas putida: Determination of absolute stereochemistry and enantiomeric excess by convergent syntheses. Tetrahedron: Asymmetry, 4(6), 1365–1386. doi: 10.1016/S0957-4166(00)80247-5
4-chlorostyrene	cis-4-chloro-1-vinylcyclohexa-4,6-diene-2,3-diol	Pseudomonas putida F39/D	+
Hudlicky, T., Boros, E. E., & Boros, C. H. (1993). New diol metabolites derived by biooxidation of chlorostyrenes with Pseudomonas putida: Determination of absolute stereochemistry and enantiomeric excess by convergent syntheses. Tetrahedron: Asymmetry, 4(6), 1365–1386. doi: 10.1016/S0957-4166(00)80247-5
4-chlorotoluene	4-chloro-cis-2,3-dihydroxy-2,3-dihydrotoluene	Pseudomonas putida F1	+
Ziffer, H., Kabuto, K., Gibson, D. T., Kobal, V. M., & Jerina, D. M. (1977). The absolute stereochemistry of several cis-dihydrodiols microbially produced from substituted benzenes. Tetrahedron, 33(19), 2491–2496. doi: 10.1016/0040-4020(77)80070-7
4-Ethylpyridine	4-ethylpyridin-3-ol	Pseudomonas putida UV4	+
Garrett, M. D., Scott, R., & Sheldrake, G. N. (2002). Enantiocomplementary preparation of (S)- and (R)-1-pyridylalkanols via ketone reduction and alkane hydroxylation using whole cells of Pseudomonas putida UV4. Tetrahedron: Asymmetry, 13(20), 2201–2204. doi: 10.1016/S0957-4166(02)00634-1
4-fluorophenyl methyl sulfide	4-fluorophenyl methyl sulfoxide	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
4-fluorotoluene	4-fluoro-cis-2,3-dihydroxy-2,3-dihydrotoluene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Hand, M. V., Groocock, M. R., Kerley, N. A., Dalton, H., … Sheldrake, G. N. (1993). Stereodirecting substituent effects during enzyme-catalysed synthesis of cis-dihydrodiol metabolites of 1,4-disubstituted benzene substrates. Journal of the Chemical Society, Chemical Communications, (11), 974. doi: 10.1039/C39930000974
4-phenyl pyridine		Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Coen GP, Hempenstall F, Ljubez V, Malone JF, Allen CC, Hamilton JT. Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates. Org Biomol Chem. 2008 Nov 7;6(21):3957-66. doi: 10.1039/b810235j. PMID: 18931802
4-Picoline	3-hydroxy-4-methyl pyridine	Escherichia coli BL21 pDTG601 todC1C2BA	+
Sakamoto T, Joern JM, Arisawa A, Arnold FH. Laboratory evolution of toluene dioxygenase to accept 4-picoline as a substrate. Appl Environ Microbiol. 2001 Sep;67(9):3882-7. PubMed Central PMCID: PMC93105. PMID: 11525981
4-propylpyridine	4-propylpyridin-3-ol	Pseudomonas putida UV4	+
Garrett, M. D., Scott, R., & Sheldrake, G. N. (2002). Enantiocomplementary preparation of (S)- and (R)-1-pyridylalkanols via ketone reduction and alkane hydroxylation using whole cells of Pseudomonas putida UV4. Tetrahedron: Asymmetry, 13(20), 2201–2204. doi: 10.1016/S0957-4166(02)00634-1
4-trifluoromethylphenyl methyl sulfide	4-trifluoromethylphenyl methyl sulfoxide	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
5-(propan-2-ylidene)cyclopenta-1,3-diene	(1R,2S)-5-isopropylidenecyclopent-3-ene-1,2-diol	Pseudomonas putida UV4	+
Bowers, N. I., Boyd, D. R., Sharma, N. D., Kennedy, M. A., Sheldrake, G. N., & Dalton, H. (1998). Stereoselective cis-dihydroxylation of azulene and related non-aromatic polyenes. Tetrahedron: Asymmetry, 9(11), 1831–1834. doi: 10.1016/S0957-4166(98)00161-X
5-(propan-2-ylidene)cyclopenta-1,3-diene	(1R,2S)-5-isopropylidenecyclopent-3-ene-1,2-diol	Pseudomonas putida UV4	+
Bowers, N. I., Boyd, D. R., Sharma, N. D., Kennedy, M. A., Sheldrake, G. N., & Dalton, H. (1998). Stereoselective cis-dihydroxylation of azulene and related non-aromatic polyenes. Tetrahedron: Asymmetry, 9(11), 1831–1834. doi: 10.1016/S0957-4166(98)00161-X
5-(propan-2-ylidene)cyclopenta-1,3-diene	(1R,2S)-5-isopropylidenecyclopent-3-ene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
5-bromo-1H-indene	5-bromoinden-1-ol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Boyle, R., Harrison, J. S., Lee, K., … Gibson, D. T. (2003). Stereochemical and mechanistic aspects of dioxygenase-catalysed benzylic hydroxylation of indene and chromane substrates. Organic & Biomolecular Chemistry, 1(8), 1298–1307. doi: 10.1039/b300898c
5-cyanoindole		Escherichia coli BL21 pDTG601a todC1C2BA	+
Kim JY, Lee K, Kim Y, Kim CK, Lee K. Production of dyestuffs from indole derivatives by naphthalene dioxygenase and toluene dioxygenase. Lett Appl Microbiol. 2003;36(6):343-8. PMID: 12753239
5-methylbenzo[b]thiophene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Brannigan, I. N., Haughey, S. A., Malone, J. F., Clarke, D. A., & Dalton, H. (1996). Dioxygenase-catalysed formation of cis/trans-dihydrodiol metabolites of mono- and bi-cyclic heteroarenes. Chemical Communications, (20), 2361. doi: 10.1039/CC9960002361
5-nitroindole		Escherichia coli BL21 pDTG601a todC1C2BA	+
Kim JY, Lee K, Kim Y, Kim CK, Lee K. Production of dyestuffs from indole derivatives by naphthalene dioxygenase and toluene dioxygenase. Lett Appl Microbiol. 2003;36(6):343-8. PMID: 12753239
5-phenyl-1,3-benzodioxole		Escherichia coli BL21 pDTG601a todC1C2BA	+
Reference under development doi:
6-bromo-1H-indene	6-bromoindan-1-one	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Boyle, R., Harrison, J. S., Lee, K., … Gibson, D. T. (2003). Stereochemical and mechanistic aspects of dioxygenase-catalysed benzylic hydroxylation of indene and chromane substrates. Organic & Biomolecular Chemistry, 1(8), 1298–1307. doi: 10.1039/b300898c
6-bromo-1H-indene	(1S)-6-bromoinden-1-ol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Boyle, R., Harrison, J. S., Lee, K., … Gibson, D. T. (2003). Stereochemical and mechanistic aspects of dioxygenase-catalysed benzylic hydroxylation of indene and chromane substrates. Organic & Biomolecular Chemistry, 1(8), 1298–1307. doi: 10.1039/b300898c
6-chloroindole		Escherichia coli BL21 pDTG601a todC1C2BA	+
Kim JY, Lee K, Kim Y, Kim CK, Lee K. Production of dyestuffs from indole derivatives by naphthalene dioxygenase and toluene dioxygenase. Lett Appl Microbiol. 2003;36(6):343-8. PMID: 12753239
6-methoxyindole		Escherichia coli BL21 pDTG601a todC1C2BA	+
Kim JY, Lee K, Kim Y, Kim CK, Lee K. Production of dyestuffs from indole derivatives by naphthalene dioxygenase and toluene dioxygenase. Lett Appl Microbiol. 2003;36(6):343-8. PMID: 12753239
6-methylfulvene	(1R,2S)-5-ethylidenecyclopenta-3-ene-1,2-diol	Pseudomonas putida UV4	+
Bowers, N. I., Boyd, D. R., Sharma, N. D., Kennedy, M. A., Sheldrake, G. N., & Dalton, H. (1998). Stereoselective cis-dihydroxylation of azulene and related non-aromatic polyenes. Tetrahedron: Asymmetry, 9(11), 1831–1834. doi: 10.1016/S0957-4166(98)00161-X
6,6-diethylfulvene	(1R,2S)-3-cyclopenta-4-dienylidenecyclopentane-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
6,7-dihydro-5H-benzocycloheptene		Pseudomonas putida F39/D	+
Resnick SM, Gibson DT. Oxidation of 6,7-dihydro-5H-benzocycloheptene by bacterial strains expressing naphthalene dioxygenase, biphenyl dioxygenase, and toluene dioxygenase yields homochiral monol or cis-diol enantiomers as major products. Appl Environ Microbiol. 1996 Apr;62(4):1364-8. PMID: 8919798
6,7,8,9-tetrahydro-5H-benzo[7]annulene	(R)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol	Pseudomonas putida UV4	+
Derek R., B., Narain D., S., Paul J., S., Jagdeep, C., David J., G., & Howard, D. (1991). Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites. Tetrahedron Letters, 32(31), 3887–3890. doi: 10.1016/S0040-4039(00)79405-6
6,7,8,9-tetrahydro-5H-benzo[7]annulene	6,7,8,9-tetrahydrobenzo[7]annulen-5-one	Pseudomonas putida UV4	+
Derek R., B., Narain D., S., Paul J., S., Jagdeep, C., David J., G., & Howard, D. (1991). Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites. Tetrahedron Letters, 32(31), 3887–3890. doi: 10.1016/S0040-4039(00)79405-6
7-bromoindole		Escherichia coli BL21 pDTG601a todC1C2BA	+
Kim JY, Lee K, Kim Y, Kim CK, Lee K. Production of dyestuffs from indole derivatives by naphthalene dioxygenase and toluene dioxygenase. Lett Appl Microbiol. 2003;36(6):343-8. PMID: 12753239
7-chloroindole		Escherichia coli BL21 pDTG601a todC1C2BA	+
Kim JY, Lee K, Kim Y, Kim CK, Lee K. Production of dyestuffs from indole derivatives by naphthalene dioxygenase and toluene dioxygenase. Lett Appl Microbiol. 2003;36(6):343-8. PMID: 12753239
9,10-dihydroanthracene	9-hydroxy-9,10-dihydroanthracene	Pseudomonas putida UV4	+
Derek R., B., Narain D., S., Paul J., S., Jagdeep, C., David J., G., & Howard, D. (1991). Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites. Tetrahedron Letters, 32(31), 3887–3890. doi: 10.1016/S0040-4039(00)79405-6
allylbenzoate		Escherichia coli BL21 pDTG601a todC1C2BA	+
Fabris F, Collins J, Sullivan B, Leisch H, Hudlicky T. Investigation of steric and functionality limits in the enzymatic dihydroxylation of benzoate esters. Versatile intermediates for the synthesis of pseudo-sugars, amino cyclitols, and bicyclic ring systems. Org Biomol Chem. 2009 Jun 21;7(12):2619-27. doi: 10.1039/b902577b. PMID: 19503938
anisole	(1S,2S)-3-methoxycyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
anisole	3-methoxy-cis-1,2-dihydroxycyclohexa-3,5-diene	Pseudomonas putida F39/D	+
Resnick, S. M., & Gibson, D. T. (1993). Biotransformation of anisole and phenetole by aerobic hydrocarbonoxidizing bacteria. Biodegradation, 4(3), 195–203. doi: 10.1007/BF00695122
anisole		Pseudomonas putida F39/D	+
Resnick, S. M., & Gibson, D. T. (1993). Biotransformation of anisole and phenetole by aerobic hydrocarbonoxidizing bacteria. Biodegradation, 4(3), 195–203. doi: 10.1007/BF00695122
azulene	(4R,5S)-4,5-dihydroazulene-4,5-diol	Pseudomonas putida UV4	+
Bowers, N. I., Boyd, D. R., Sharma, N. D., Kennedy, M. A., Sheldrake, G. N., & Dalton, H. (1998). Stereoselective cis-dihydroxylation of azulene and related non-aromatic polyenes. Tetrahedron: Asymmetry, 9(11), 1831–1834. doi: 10.1016/S0957-4166(98)00161-X
Benzene	cis-dihydrobenzenediol	Pseudomonas putida F39/D	+
Gibson, D. T., Cardini, G. E., Maseles, F. C., & Kallio, R. E. (1970). Oxidative degradation of aromatic hydrocarbons by microorganisms. IV. Incorporation of oxygen-18 into benzene by Pseudomonas putida. Biochemistry, 9(7), 1631–1635. doi: 10.1021/bi00809a024
benzocyclobutene	(8R)-bicyclo[4.2.0]octa-1,3,5-trien-8-ol	Pseudomonas putida UV4	+
Derek R., B., Narain D., S., Paul J., S., Jagdeep, C., David J., G., & Howard, D. (1991). Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites. Tetrahedron Letters, 32(31), 3887–3890. doi: 10.1016/S0040-4039(00)79405-6
benzocyclobutene	Benzocyclobuten-1(2H)-one	Pseudomonas putida UV4	+
Derek R., B., Narain D., S., Paul J., S., Jagdeep, C., David J., G., & Howard, D. (1991). Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites. Tetrahedron Letters, 32(31), 3887–3890. doi: 10.1016/S0040-4039(00)79405-6
benzocyclobutene	(7R,8S)-bicyclo[4.2.0]octa-1,3,5-triene-7,8-diol	Pseudomonas putida UV4	+
Derek R., B., Narain D., S., Paul J., S., Jagdeep, C., David J., G., & Howard, D. (1991). Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites. Tetrahedron Letters, 32(31), 3887–3890. doi: 10.1016/S0040-4039(00)79405-6
benzocyclobutene	(2R,3S)-bicyclo[4.2.0]octa-1(6),4-diene-2,3-diol	Pseudomonas putida UV4	+
Derek R., B., Narain D., S., Paul J., S., Jagdeep, C., David J., G., & Howard, D. (1991). Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites. Tetrahedron Letters, 32(31), 3887–3890. doi: 10.1016/S0040-4039(00)79405-6
benzocyclobutene	(1R,2S)-bicyclo[4.2.0]octa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Derek R., B., Narain D., S., Paul J., S., Jagdeep, C., David J., G., & Howard, D. (1991). Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites. Tetrahedron Letters, 32(31), 3887–3890. doi: 10.1016/S0040-4039(00)79405-6
benzocyclobutene		Pseudomonas putida UV4	+
Derek R., B., Narain D., S., Paul J., S., Jagdeep, C., David J., G., & Howard, D. (1991). Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites. Tetrahedron Letters, 32(31), 3887–3890. doi: 10.1016/S0040-4039(00)79405-6
benzocyclobutene		Pseudomonas putida UV4	+
Derek R., B., Narain D., S., Paul J., S., Jagdeep, C., David J., G., & Howard, D. (1991). Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites. Tetrahedron Letters, 32(31), 3887–3890. doi: 10.1016/S0040-4039(00)79405-6
benzocyclohept-1-ene		Pseudomonas putida F39/D	+
Resnick SM, Gibson DT. Oxidation of 6,7-dihydro-5H-benzocycloheptene by bacterial strains expressing naphthalene dioxygenase, biphenyl dioxygenase, and toluene dioxygenase yields homochiral monol or cis-diol enantiomers as major products. Appl Environ Microbiol. 1996 Apr;62(4):1364-8. PMID: 8919798
benzofuran	6-hydroxybenzofuran	Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
benzofuran		Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
benzonitrile	cis-(1S,2R)-1,2-dihydroxy-3-cyanocyclohexa-3,5-diene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
benzothiophene	2,3-dihydro-benzo[b]thiophene-2,3-diol	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, McMurray B, Haughey SA, Allen CC, Hamilton JT, McRoberts WC, O'Ferrall RA, Nikodinovic-Runic J, Coulombel LA, O'Connor KE. Bacterial dioxygenase- and monooxygenase-catalysed sulfoxidation of benzo[b]thiophenes. Org Biomol Chem. 2012 Jan 28;10(4):782-90. doi: 10.1039/c1ob06678a. PubMed PMID: PMID: 22134441
benzothiophene	(4R,5S)-4,5-dihydro-benzo[b]thiophene-4,5-diol	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, McMurray B, Haughey SA, Allen CC, Hamilton JT, McRoberts WC, O'Ferrall RA, Nikodinovic-Runic J, Coulombel LA, O'Connor KE. Bacterial dioxygenase- and monooxygenase-catalysed sulfoxidation of benzo[b]thiophenes. Org Biomol Chem. 2012 Jan 28;10(4):782-90. doi: 10.1039/c1ob06678a. PubMed PMID: PMID: 22134441
benzothiophene	Benzo[b]naphtho[1,2-d]thiophene, 7-oxide	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, McMurray B, Haughey SA, Allen CC, Hamilton JT, McRoberts WC, O'Ferrall RA, Nikodinovic-Runic J, Coulombel LA, O'Connor KE. Bacterial dioxygenase- and monooxygenase-catalysed sulfoxidation of benzo[b]thiophenes. Org Biomol Chem. 2012 Jan 28;10(4):782-90. doi: 10.1039/c1ob06678a. PubMed PMID: PMID: 22134441
benzothiophene	Benzo[b]naphtho[1,2-d]thiophene	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, McMurray B, Haughey SA, Allen CC, Hamilton JT, McRoberts WC, O'Ferrall RA, Nikodinovic-Runic J, Coulombel LA, O'Connor KE. Bacterial dioxygenase- and monooxygenase-catalysed sulfoxidation of benzo[b]thiophenes. Org Biomol Chem. 2012 Jan 28;10(4):782-90. doi: 10.1039/c1ob06678a. PubMed PMID: PMID: 22134441
benzothiophene	5-hydroxybenzothiophene	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, McMurray B, Haughey SA, Allen CC, Hamilton JT, McRoberts WC, O'Ferrall RA, Nikodinovic-Runic J, Coulombel LA, O'Connor KE. Bacterial dioxygenase- and monooxygenase-catalysed sulfoxidation of benzo[b]thiophenes. Org Biomol Chem. 2012 Jan 28;10(4):782-90. doi: 10.1039/c1ob06678a. PubMed PMID: PMID: 22134441
benzothiophene	1-benzothiophen-4-ol	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, McMurray B, Haughey SA, Allen CC, Hamilton JT, McRoberts WC, O'Ferrall RA, Nikodinovic-Runic J, Coulombel LA, O'Connor KE. Bacterial dioxygenase- and monooxygenase-catalysed sulfoxidation of benzo[b]thiophenes. Org Biomol Chem. 2012 Jan 28;10(4):782-90. doi: 10.1039/c1ob06678a. PubMed PMID: PMID: 22134441
benzothiophene	5-hydroxybenzothiophene	Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
benzothiophene	2,3-dihydro-benzo[b]thiophene-2,3-diol	Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
biphenyl	cis-2,3-dihydroxy-1-phenylcyclohexa-4,6-diene	Pseudomonas putida F1	+
Furukawa K, Hirose J, Suyama A, Zaiki T, Hayashida S. Gene components responsible for discrete substrate specificity in the metabolism of biphenyl (bph operon) and toluene (tod operon). J Bacteriol. 1993 Aug;175(16):5224-32. PubMed Central PMCID: PMC204990. PMID: 8349562
Biphenylene	(1S,8bS)-biphenylene-1,8b(1H)-diol	Pseudomonas putida UV4	+
Derek R., B., Narain D., S., Paul J., S., Jagdeep, C., David J., G., & Howard, D. (1991). Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites. Tetrahedron Letters, 32(31), 3887–3890. doi: 10.1016/S0040-4039(00)79405-6
bromobenzene	3-bromo-cis-1,2-dihydroxycyclohexa-3,5-diene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
chlorobenzene	3-chloro-cis-1,2-dihydroxycyclohexa-3,5-diene	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
chroman-4-ol	4-Chromanone	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Boyle, R., Harrison, J. S., Lee, K., … Gibson, D. T. (2003). Stereochemical and mechanistic aspects of dioxygenase-catalysed benzylic hydroxylation of indene and chromane substrates. Organic & Biomolecular Chemistry, 1(8), 1298–1307. doi: 10.1039/b300898c
chromane	(4R)-chroman-4-ol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Boyle, R., Harrison, J. S., Lee, K., … Gibson, D. T. (2003). Stereochemical and mechanistic aspects of dioxygenase-catalysed benzylic hydroxylation of indene and chromane substrates. Organic & Biomolecular Chemistry, 1(8), 1298–1307. doi: 10.1039/b300898c
chromane	4-Chromanone	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Boyle, R., Harrison, J. S., Lee, K., … Gibson, D. T. (2003). Stereochemical and mechanistic aspects of dioxygenase-catalysed benzylic hydroxylation of indene and chromane substrates. Organic & Biomolecular Chemistry, 1(8), 1298–1307. doi: 10.1039/b300898c
cis-1-bromopropene		Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
cis-1-chloro-1-propene		Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
cis-1,2-dichloroethene		Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
cis-1,4-dichloro-2-butene		Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
cis-2-chloro-2-butene		Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
cis-2-heptene		Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
cis-2-hexene	Hexane-2,3-diol	Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
cis-2-octene	Octane-2,3-diol	Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
cis-2-pentene	Pentane-2,3-diol	Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
cis-dibromoethylene		Pseudomonas putida F1	+
McClay K, Fox BG, Steffan RJ. Chloroform mineralization by toluene-oxidizing bacteria. Appl Environ Microbiol. 1996 Aug;62(8):2716-22. PMID: 8702263
cyclohexene	cis-cyclohexane-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
dihydrobenzofuran		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Boyle, R., Malone, J. F., Chima, J., & Dalton, H. (1993). Structures and stereochemical assignments of some novel chiral synthons derived from the biotransformation of 2,3-dihydrobenzofuran and benzofuran by Pseudomonas putida. Tetrahedron: Asymmetry, 4(6), 1307–1324. doi: 10.1016/S0957-4166(00)80242-6
diphenyl sulfide	(1S,2S)-3-(phenylthio)cyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
Diphenylmethane		Escherichia coli JM109 pJHF3051	+
Shindo K, Ohnishi Y, Chun HK, Takahashi H, Hayashi M, Saito A, Iguchi K, Furukawa K, Harayama S, Horinouchi S, Misawa N. Oxygenation reactions of various tricyclic fused aromatic compounds using Escherichia coli and Streptomyces lividans transformants carrying several arene dioxygenase genes. Biosci Biotechnol Biochem. 2001 Nov;65(11):2472-81. PMID: 11791721
E-beta-bromostyrene	(1R,2S)-3-((E)-2-bromovinyl)cyclohexa-3,5-diene-1,2-diol	Escherichia coli BL21 pDTG601a todC1C2BA	+
Novak, B. H., & Hudlicky, T. (1999). New arene cis-dihydrodiol metabolites from β-bromostyrenes. Tetrahedron: Asymmetry, 10(11), 2067–2069. doi: 10.1016/S0957-4166(99)00237-2
ethyl phenyl sulfide	Ethylphenylsulfoxide	Pseudomonas putida F1	+
Lee K, Brand JM, Gibson DT. Stereospecific sulfoxidation by toluene and naphthalene dioxygenases. Biochem Biophys Res Commun. 1995 Jul 6;212(1):9-15. PMID: 7612022
ethylbenzene	3-ethyl-cis-1,2-dihydroxycyclohexa-3,5-diene	Pseudomonas putida F1	+
Gibson DT, Gschwendt B, Yeh WK, Kobal VM. Initial reactions in the oxidation of ethylbenzene by Pseudomonas putida. Biochemistry. 1973 Apr 10;12(8):1520-8. PMID: 4699984
ethylbenzoate		Escherichia coli BL21 pDTG601a todC1C2BA	+
Fabris F, Collins J, Sullivan B, Leisch H, Hudlicky T. Investigation of steric and functionality limits in the enzymatic dihydroxylation of benzoate esters. Versatile intermediates for the synthesis of pseudo-sugars, amino cyclitols, and bicyclic ring systems. Org Biomol Chem. 2009 Jun 21;7(12):2619-27. doi: 10.1039/b902577b. PMID: 19503938
ethynylbenzene	(1S,2R)-3-ethynylcyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
ethynylbenzene	3-ethynyl-cis-1,2-dihydroxycyclohexa-3,5-diene	Pseudomonas putida F39/D	+
Stabile, M. R., Hudlicky, T., & Meisels, M. L. (1995). New chiral synthon from bromoethylbenzene: Absolute stereochemistry of a biooxidation metabolite. Tetrahedron: Asymmetry, 6(2), 537–542. doi: 10.1016/0957-4166(95)00037-P
ethynylbenzene	(1S,2R)-3-ethynylcyclohexa-3,5-diene-1,2-diol	Pseudomonas putida F39/D	+
Hudlicky, T., Luna, H., Barbieri, G., & Kwart, L. D. (1988). Enantioselective synthesis through microbial oxidation of arenes. 1. Efficient preparation of terpene and prostanoid synthons. Journal of the American Chemical Society, 110(14), 4735–4741. doi: 10.1021/ja00222a035
fluorene	Fluoren-9-one	Pseudomonas putida UV4	+
Derek R., B., Narain D., S., Paul J., S., Jagdeep, C., David J., G., & Howard, D. (1991). Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites. Tetrahedron Letters, 32(31), 3887–3890. doi: 10.1016/S0040-4039(00)79405-6
furan		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Brannigan, I. N., Haughey, S. A., Malone, J. F., Clarke, D. A., & Dalton, H. (1996). Dioxygenase-catalysed formation of cis/trans-dihydrodiol metabolites of mono- and bi-cyclic heteroarenes. Chemical Communications, (20), 2361. doi: 10.1039/CC9960002361
i-propylbenzoate		Escherichia coli BL21 pDTG601a todC1C2BA	+
Fabris F, Collins J, Sullivan B, Leisch H, Hudlicky T. Investigation of steric and functionality limits in the enzymatic dihydroxylation of benzoate esters. Versatile intermediates for the synthesis of pseudo-sugars, amino cyclitols, and bicyclic ring systems. Org Biomol Chem. 2009 Jun 21;7(12):2619-27. doi: 10.1039/b902577b. PMID: 19503938
i-propylphenylsulfide	isopropylphenylsulfoxide	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
indan	(1R)-indanol	Escherichia coli BL21 pDTG601 todC1C2BA	+
Brand JM, Cruden DL, Zylstra GJ, Gibson DT. Stereospecific hydroxylation of indan by Escherichia coli containing the cloned toluene dioxygenase genes from Pseudomonas putida F1. Appl Environ Microbiol. 1992 Oct;58(10):3407-9. Erratum in: Appl Environ Microbiol 1993 Jan;59(1):351. PubMed PMID: 1444374
indan	trans-1,3-indandiol	Escherichia coli BL21 pDTG601 todC1C2BA	+
Brand JM, Cruden DL, Zylstra GJ, Gibson DT. Stereospecific hydroxylation of indan by Escherichia coli containing the cloned toluene dioxygenase genes from Pseudomonas putida F1. Appl Environ Microbiol. 1992 Oct;58(10):3407-9. Erratum in: Appl Environ Microbiol 1993 Jan;59(1):351. PubMed PMID: 1444374
indan	trans-1,3-indandiol	Pseudomonas putida F39/D	+
Brand JM, Cruden DL, Zylstra GJ, Gibson DT. Stereospecific hydroxylation of indan by Escherichia coli containing the cloned toluene dioxygenase genes from Pseudomonas putida F1. Appl Environ Microbiol. 1992 Oct;58(10):3407-9. Erratum in: Appl Environ Microbiol 1993 Jan;59(1):351. PubMed PMID: 1444374
indan	(1R)-indanol	Pseudomonas putida F39/D	+
Brand JM, Cruden DL, Zylstra GJ, Gibson DT. Stereospecific hydroxylation of indan by Escherichia coli containing the cloned toluene dioxygenase genes from Pseudomonas putida F1. Appl Environ Microbiol. 1992 Oct;58(10):3407-9. Erratum in: Appl Environ Microbiol 1993 Jan;59(1):351. PubMed PMID: 1444374
indan	1-indanone	Pseudomonas putida F39/D	+
Brand JM, Cruden DL, Zylstra GJ, Gibson DT. Stereospecific hydroxylation of indan by Escherichia coli containing the cloned toluene dioxygenase genes from Pseudomonas putida F1. Appl Environ Microbiol. 1992 Oct;58(10):3407-9. Erratum in: Appl Environ Microbiol 1993 Jan;59(1):351. PubMed PMID: 1444374
indan	(1R)-indanol	Pseudomonas putida UV4	+
Gibson DT, Resnick SM, Lee K, Brand JM, Torok DS, Wackett LP, Schocken MJ, Haigler BE. Desaturation, dioxygenation, and monooxygenation reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp. strain 9816-4. J Bacteriol. 1995 May;177(10):2615-21. PubMed Central PMCID: PMC176929. PMID: 7751268
indene	(1S)-indenol	Pseudomonas putida F39/D	+
Brand JM, Cruden DL, Zylstra GJ, Gibson DT. Stereospecific hydroxylation of indan by Escherichia coli containing the cloned toluene dioxygenase genes from Pseudomonas putida F1. Appl Environ Microbiol. 1992 Oct;58(10):3407-9. Erratum in: Appl Environ Microbiol 1993 Jan;59(1):351. PubMed PMID: 1444374
indene	(1R)-indenol	Pseudomonas putida UV4	+
Gibson DT, Resnick SM, Lee K, Brand JM, Torok DS, Wackett LP, Schocken MJ, Haigler BE. Desaturation, dioxygenation, and monooxygenation reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp. strain 9816-4. J Bacteriol. 1995 May;177(10):2615-21. PubMed Central PMCID: PMC176929. PMID: 7751268
iodobenzene	3-Iodobenzene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
isopropenylbenzene	(1S,2R)-3-(prop-1-en-2-yl)cyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Bowers, N. I., Brannigan, I. N., Groocock, M. R., Malone, J. F., … Allen, C. C. R. (2005). Biocatalytic Asymmetric Dihydroxylation of Conjugated Mono- and Poly-alkenes to Yield Enantiopure Cycliccis-Diols. Advanced Synthesis & Catalysis, 347(7-8), 1081–1089. doi: 10.1002/adsc.200505033
isopropylbenzene		Pseudomonas putida F1	+
Leahy JG, Tracy KD, Eley MH. Degradation of mixtures of aromatic and chloroaliphatic hydrocarbons by aromatic hydrocarbon-degrading bacteria. FEMS Microbiol Ecol. 2003 Mar 1;43(2):271-6. doi: 10.1111/j.1574-6941.2003.tb01067.x. PMID: 19719688
isoquinoline	2-hydroxyisoquinoline	Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
isoquinoline	isoquinolin-4-ol	Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
isoquinoline	Isoquinolin-5-ol	Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
isoquinoline	8-hydroxyisoquinoline	Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
m-nitrotoluene	(3-nitrophenyl)methanol	Pseudomonas putida F1	+
Robertson JB, Spain JC, Haddock JD, Gibson DT. Oxidation of nitrotoluenes by toluene dioxygenase: evidence for a monooxygenase reaction. Appl Environ Microbiol. 1992 Aug;58(8):2643-8. PubMed Central PMCID: PMID: 1514810
m-xylene	3,5-dimethyl-cis-1,2-dihydroxycyclohexa-3,5-diene	Pseudomonas putida F39/D	+
Gibson DT, Mahadevan V, Davey JF. Bacterial metabolism of para- and meta-xylene: oxidation of the aromatic ring. J Bacteriol. 1974 Sep;119(3):930-6. PubMed Central PMCID: PMC245701. PMID: 4850728
m-xylene	2,4-dimethylphenol	Pseudomonas putida F39/D	+
Gibson DT, Mahadevan V, Davey JF. Bacterial metabolism of para- and meta-xylene: oxidation of the aromatic ring. J Bacteriol. 1974 Sep;119(3):930-6. PubMed Central PMCID: PMC245701. PMID: 4850728
methoxylmethyl phenyl sulfide	methoxylmethyl phenyl sulfoxide	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
methyl p-nitrophenyl sulfide	Methyl p-nitrophenyl sulfoxide	Pseudomonas putida F1	+
Lee K, Brand JM, Gibson DT. Stereospecific sulfoxidation by toluene and naphthalene dioxygenases. Biochem Biophys Res Commun. 1995 Jul 6;212(1):9-15. PMID: 7612022
methyl p-tolyl sulfide	cis-2,3-dihydroxy-2,3-dihydro-1-methyl-4-(methylthio)-benzene	Pseudomonas putida F1	+
Lee K, Brand JM, Gibson DT. Stereospecific sulfoxidation by toluene and naphthalene dioxygenases. Biochem Biophys Res Commun. 1995 Jul 6;212(1):9-15. PMID: 7612022
methyl p-tolyl sulfide		Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
methyl p-tolyl sulfide	4-methylphenyl methyl sulfoxide	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
methyl phenyl sulfide	methylphenylsulfoxide	Pseudomonas putida F1	+
Lee K, Brand JM, Gibson DT. Stereospecific sulfoxidation by toluene and naphthalene dioxygenases. Biochem Biophys Res Commun. 1995 Jul 6;212(1):9-15. PMID: 7612022
methyl phenyl sulfide	methylphenylsulfoxide	Pseudomonas putida UV4	+
Lee K, Brand JM, Gibson DT. Stereospecific sulfoxidation by toluene and naphthalene dioxygenases. Biochem Biophys Res Commun. 1995 Jul 6;212(1):9-15. PMID: 7612022
methylbenzoate		Escherichia coli BL21 pDTG601a todC1C2BA	+
Fabris F, Collins J, Sullivan B, Leisch H, Hudlicky T. Investigation of steric and functionality limits in the enzymatic dihydroxylation of benzoate esters. Versatile intermediates for the synthesis of pseudo-sugars, amino cyclitols, and bicyclic ring systems. Org Biomol Chem. 2009 Jun 21;7(12):2619-27. doi: 10.1039/b902577b. PMID: 19503938
methylsulfanylmethylsulfanylbenzene	(S)-methyl((phenylsulfinyl)methyl)sulfane	Pseudomonas putida UV4	+
Alien, C. C. R., Boyd, D. R., Dalton, H., Sharma, N. D., Haughey, S. A., McMordie, R. A. S., … Sproule, K. (1995). Sulfoxides of high enantiopurity from bacterial dioxygenase-catalysed oxidation. Journal of the Chemical Society, Chemical Communications, (2), 119. doi: 10.1039/C39950000119
n-butyl-benzene		Escherichia coli JM109 pJHF3051	+
Shindo K, Ohnishi Y, Chun HK, Takahashi H, Hayashi M, Saito A, Iguchi K, Furukawa K, Harayama S, Horinouchi S, Misawa N. Oxygenation reactions of various tricyclic fused aromatic compounds using Escherichia coli and Streptomyces lividans transformants carrying several arene dioxygenase genes. Biosci Biotechnol Biochem. 2001 Nov;65(11):2472-81. PMID: 11791721
n-butyl-benzene		Pseudomonas putida F1	+
Shindo K, Ohnishi Y, Chun HK, Takahashi H, Hayashi M, Saito A, Iguchi K, Furukawa K, Harayama S, Horinouchi S, Misawa N. Oxygenation reactions of various tricyclic fused aromatic compounds using Escherichia coli and Streptomyces lividans transformants carrying several arene dioxygenase genes. Biosci Biotechnol Biochem. 2001 Nov;65(11):2472-81. PMID: 11791721
n-butyl-benzene		Pseudomonas putida F39/D	+
Shindo K, Ohnishi Y, Chun HK, Takahashi H, Hayashi M, Saito A, Iguchi K, Furukawa K, Harayama S, Horinouchi S, Misawa N. Oxygenation reactions of various tricyclic fused aromatic compounds using Escherichia coli and Streptomyces lividans transformants carrying several arene dioxygenase genes. Biosci Biotechnol Biochem. 2001 Nov;65(11):2472-81. PMID: 11791721
n-butyl-benzene	(1S,2R)-3-butylcyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
n-butylphenylsulfide	n-butyl phenyl sulfoxide	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
n-heptyl-phenyl sulfide		Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
n-hexyl-phenyl sulfide		Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
n-octyl-phenyl sulfide		Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
n-pentyl phenyl sulfide	n-pentyl phenyl sulfoxide	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
n-propylbenzene		Pseudomonas putida F39/D	+
Gibson DT, Gschwendt B, Yeh WK, Kobal VM. Initial reactions in the oxidation of ethylbenzene by Pseudomonas putida. Biochemistry. 1973 Apr 10;12(8):1520-8. PMID: 4699984
n-propylbenzene		Pseudomonas putida F1	+
Gibson DT, Gschwendt B, Yeh WK, Kobal VM. Initial reactions in the oxidation of ethylbenzene by Pseudomonas putida. Biochemistry. 1973 Apr 10;12(8):1520-8. PMID: 4699984
n-propylbenzoate		Escherichia coli BL21 pDTG601a todC1C2BA	+
Fabris F, Collins J, Sullivan B, Leisch H, Hudlicky T. Investigation of steric and functionality limits in the enzymatic dihydroxylation of benzoate esters. Versatile intermediates for the synthesis of pseudo-sugars, amino cyclitols, and bicyclic ring systems. Org Biomol Chem. 2009 Jun 21;7(12):2619-27. doi: 10.1039/b902577b. PMID: 19503938
n-propylphenylsulfide		Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
naphthalene		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Kerley, N. A., McMordie, R. A. S., Sheldrake, G. N., Williams, P., & Dalton, H. (1996). Dioxygenase-catalysed oxidation of dihydronaphthalenes to yield arene hydrate and cis-dihydro naphthalenediols. Journal of the Chemical Society, Perkin Transactions 1, (1), 67. doi: 10.1039/P19960000067
naphthalene	(+)-(1R,2S)-cis-1,2-dihydroxy-1,2-dihydronaphthalene	Pseudomonas putida F39/D	+
Torok DS, Resnick SM, Brand JM, Cruden DL, Gibson DT. Desaturation and oxygenation of 1,2-dihydronaphthalene by toluene and naphthalene dioxygenase. J Bacteriol. 1995 Oct;177(20):5799-805. PubMed Central PMCID: PMID: 7592326
o-bromostyrene	(1S,2R)-4-bromo-3-ethenylcyclohexa-3,5-diene-1,2-diol	Pseudomonas putida F39/D	+
Königsberger, K., & Hudlicky, T. (1993). Microbial oxidation of 2-bromostyrene by Pseudomonas Putida 39/D. Isolation and identification of metabolites. Tetrahedron: Asymmetry, 4(12), 2469–2474. doi: 10.1016/S0957-4166(00)82225-9
o-nitrotoluene	(2-Nitrophenyl)methanol	Pseudomonas putida F1	+
Robertson JB, Spain JC, Haddock JD, Gibson DT. Oxidation of nitrotoluenes by toluene dioxygenase: evidence for a monooxygenase reaction. Appl Environ Microbiol. 1992 Aug;58(8):2643-8. PubMed Central PMCID: PMID: 1514810
p-dichlorobenzene	3,6-dichlorocatechol	Pseudomonas putida F1	+
Spain JC, Zylstra GJ, Blake CK, Gibson DT. Monohydroxylation of phenol and 2,5-dichlorophenol by toluene dioxygenase in Pseudomonas putida F1. Appl Environ Microbiol. 1989 Oct;55(10):2648-52. Erratum in: Appl Environ Microbiol 1991 May;57(5):1579. PubMed Central PMCID: PMC203138. PMID: 2604403
p-dichlorobenzene	(1R,2S)-3,6-dichlorocyclohexa-3,5-diene-1,2-diol	Pseudomonas putida F1	+
Spain JC, Zylstra GJ, Blake CK, Gibson DT. Monohydroxylation of phenol and 2,5-dichlorophenol by toluene dioxygenase in Pseudomonas putida F1. Appl Environ Microbiol. 1989 Oct;55(10):2648-52. Erratum in: Appl Environ Microbiol 1991 May;57(5):1579. PubMed Central PMCID: PMC203138. PMID: 2604403
p-methoxyphenyl methyl sulfide	p-Methoxyphenyl methyl sulfoxide	Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
p-methoxyphenyl methyl sulfide	p-methoxyphenylmethylsulfoxide	Pseudomonas putida F1	+
Lee K, Brand JM, Gibson DT. Stereospecific sulfoxidation by toluene and naphthalene dioxygenases. Biochem Biophys Res Commun. 1995 Jul 6;212(1):9-15. PMID: 7612022
p-nitrotoluene	2-methyl-5-nitrophenol	Pseudomonas putida F1	+
Robertson JB, Spain JC, Haddock JD, Gibson DT. Oxidation of nitrotoluenes by toluene dioxygenase: evidence for a monooxygenase reaction. Appl Environ Microbiol. 1992 Aug;58(8):2643-8. PubMed Central PMCID: PMID: 1514810
p-nitrotoluene	3-methyl-6-nitrocatechol	Pseudomonas putida F1	+
Robertson JB, Spain JC, Haddock JD, Gibson DT. Oxidation of nitrotoluenes by toluene dioxygenase: evidence for a monooxygenase reaction. Appl Environ Microbiol. 1992 Aug;58(8):2643-8. PubMed Central PMCID: PMID: 1514810
p-xylene	3,6-dimethyl-cis-1,2-dihydroxycyclohexa-3,5-diene	Pseudomonas putida F39/D	+
Gibson DT, Mahadevan V, Davey JF. Bacterial metabolism of para- and meta-xylene: oxidation of the aromatic ring. J Bacteriol. 1974 Sep;119(3):930-6. PubMed Central PMCID: PMC245701. PMID: 4850728
phenetole	(1S,2S)-3-ethoxycyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
phenetole	3-ethoxy-cis-1,2-dihydroxycyclohexa-3,5-diene	Pseudomonas putida F39/D	+
Resnick, S. M., & Gibson, D. T. (1993). Biotransformation of anisole and phenetole by aerobic hydrocarbonoxidizing bacteria. Biodegradation, 4(3), 195–203. doi: 10.1007/BF00695122
phenetole	2-ethoxyphenol	Pseudomonas putida F39/D	+
Resnick, S. M., & Gibson, D. T. (1993). Biotransformation of anisole and phenetole by aerobic hydrocarbonoxidizing bacteria. Biodegradation, 4(3), 195–203. doi: 10.1007/BF00695122
phenol	catechol	Pseudomonas putida F1	+
Spain JC, Zylstra GJ, Blake CK, Gibson DT. Monohydroxylation of phenol and 2,5-dichlorophenol by toluene dioxygenase in Pseudomonas putida F1. Appl Environ Microbiol. 1989 Oct;55(10):2648-52. Erratum in: Appl Environ Microbiol 1991 May;57(5):1579. PubMed Central PMCID: PMC203138. PMID: 2604403
phenyl vinyl sulphide		Pseudomonas putida UV4	+
Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CC. Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation. Org Biomol Chem. 2004 Sep 7;2(17):2530-7. PubMed PMID: PMID: 15326534
phenylmethyl acetate	[(5S,6R)-5,6-dihydroxy-1-cyclohexa-1,3-dienyl]methyl acetate	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
prop-2-yn-1-yl benzoate		Escherichia coli BL21 pDTG601a todC1C2BA	+
Fabris F, Collins J, Sullivan B, Leisch H, Hudlicky T. Investigation of steric and functionality limits in the enzymatic dihydroxylation of benzoate esters. Versatile intermediates for the synthesis of pseudo-sugars, amino cyclitols, and bicyclic ring systems. Org Biomol Chem. 2009 Jun 21;7(12):2619-27. doi: 10.1039/b902577b. PMID: 19503938
quinazoline		Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Dorrity, M. R. J., Hand, M. V., McMordie, R. A. S., Malone, J. F., … Sheldrake, G. N. (1993). Structure and stereochemistry of cis-dihydro diol and phenol metabolites of bicyclic azaarenes from Pseudomonas putida UV4. Journal of the Chemical Society, Perkin Transactions 1, (9), 1065. doi: 10.1039/P19930001065
quinoline	quinolin-3-ol	Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
quinoline	quinolin-8-ol	Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
quinoline	(5R,6S)-5,6-dihydroquinoline-5,6-diol	Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
quinoline	(7S,8R)-7,8-dihydroquinoline-7,8-diol	Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
quinoxaline	2-hydroxyquinoxaline	Pseudomonas putida UV4	+
Barr, S. A., Boyd, D. R., Sharma, N. D., Hamilton, L., Austin, R., McMordie, S., & Dalton, H. (1994). Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the “NIH shift.” J. Chem. Soc., Chem. Commun., (17), 1921–1922. doi: 10.1039/C39940001921
styrene	3-ethenyl-cis-1,2-dihydroxycyclohexa-3,5-diene	Pseudomonas putida F39/D	+
Hudlicky, T., Boros, E. E., & Boros, C. H. (1993). New diol metabolites derived by biooxidation of chlorostyrenes with Pseudomonas putida: Determination of absolute stereochemistry and enantiomeric excess by convergent syntheses. Tetrahedron: Asymmetry, 4(6), 1365–1386. doi: 10.1016/S0957-4166(00)80247-5
styrene	(1S,2R)-3-ethenylcyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
t-butyl benzene		Escherichia coli JM109 pJHF3051	+
Shindo K, Ohnishi Y, Chun HK, Takahashi H, Hayashi M, Saito A, Iguchi K, Furukawa K, Harayama S, Horinouchi S, Misawa N. Oxygenation reactions of various tricyclic fused aromatic compounds using Escherichia coli and Streptomyces lividans transformants carrying several arene dioxygenase genes. Biosci Biotechnol Biochem. 2001 Nov;65(11):2472-81. PMID: 11791721
t-butyl phenyl sulfide	(1S,2S)-3-(tert-butylthio)cyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
Toluene	3-Methylbenzene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
Toluene	(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol	Pseudomonas putida F1	+
Wackett LP, Kwart LD, Gibson DT. Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putida. Biochemistry. 1988 Feb 23;27(4):1360-7. PMID: 3365392
Toluene	(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol	Pseudomonas putida F39/D	+
Wackett LP, Kwart LD, Gibson DT. Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putida. Biochemistry. 1988 Feb 23;27(4):1360-7. PMID: 3365392
trans-1-chloro-1-propene		Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
trans-1,4-dichloro-2-butene	1,4-Dichloro-2-butanone	Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
trans-2-chloro-2-butene		Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
trans-2-hexene	Hexane-2,3-diol	Escherichia coli BL21 pDTG601a todC1C2BA	+
Lange CC, Wackett LP. Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification. J Bacteriol. 1997 Jun;179(12):3858-65. PubMed Central PMCID: PMC179193. PMID: 9190800
trans-cinnamonitrile	(E)-3-((5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl)acrylonitrile	Pseudomonas putida F1	+
Keener WK, Watwood ME, Apel WA. Activity-dependent fluorescent labeling of bacteria that degrade toluene via toluene 2,3-dioxygenase. Appl Microbiol Biotechnol. 1998 Apr;49(4):455-62. PMID: 9615486
trans-dibromoethylene		Pseudomonas putida F1	+
McClay K, Fox BG, Steffan RJ. Chloroform mineralization by toluene-oxidizing bacteria. Appl Environ Microbiol. 1996 Aug;62(8):2716-22. PMID: 8702263
trichloroethene	Formate	Pseudomonas putida F1	+
Wackett LP, Gibson DT. Degradation of trichloroethylene by toluene dioxygenase in whole-cell studies with Pseudomonas putida F1. Appl Environ Microbiol. 1988 Jul;54(7):1703-8. PubMed Central PMCID: PMC202732. PMID: 3415234
trichloroethene	Glyoxylate	Pseudomonas putida F1	+
Wackett LP, Gibson DT. Degradation of trichloroethylene by toluene dioxygenase in whole-cell studies with Pseudomonas putida F1. Appl Environ Microbiol. 1988 Jul;54(7):1703-8. PubMed Central PMCID: PMC202732. PMID: 3415234
trifluoromethyl benzene	(1S,2R)-3-(trifluoromethyl)cyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
trifluoromethyl benzene	(1R,2S)-3-(trifluoromethyl)cyclohexa-3,5-diene-1,2-diol	Pseudomonas putida UV4	+
Boyd, D. R., Sharma, N. D., Byrne, B., Hand, M. V., Malone, J. F., Sheldrake, G. N., … Dalton, H. (1998). Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. Journal of the Chemical Society, Perkin Transactions 1, (12), 1935–1944. doi: 10.1039/A800809D
Z-beta-bromostyrene	(1R,2S)-3-((Z)-2-bromovinyl)cyclohexa-3,5-diene-1,2-diol	Escherichia coli BL21 pDTG601a todC1C2BA	+
Novak, B. H., & Hudlicky, T. (1999). New arene cis-dihydrodiol metabolites from β-bromostyrenes. Tetrahedron: Asymmetry, 10(11), 2067–2069. doi: 10.1016/S0957-4166(99)00237-2