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Naphthalene 1,2-dioxygenase

natively expressed by: Pseudomonas sp. NCIB 9816-4

Substrates:

(1R)-indanol (1S)-indanol (S)-1-phenethyl alcohol [2-(methylsulfanyl)ethyl]benzene 1-methylisoquinoline 1-methylpyridin-2-one 1-Phenylethanone 1-phenylpyrazole 1-phenylpyrrole 1,1-diphenylethylene 1,2-dihydronaphthalene 1,2,3,4-tetrahydronaphthalene 1,2,3,5,6,7-hexahydro-S-indacene 1,3-cycloheptadiene 1,3-cyclohexadiene 1,3-cyclooctadiene 1,3,5-cycloheptatriene 1,3,5-trimethylbenzene 1,5-dimethylnaphthalene 1,5-naphthyridine 1,8-dimethylnaphthalene 2-bromo naphthalene 2-chloro naphthalene 2-chlorophenol 2-ethyl naphthalene 2-indanone 2-methyl naphthalene 2-methylbenzothiophene 2-methylquinoline 2,6-dimethylnaphthalene 2,7-dimethylnaphthalene 3-chlorophenol 3-methylbenzothiophene 3-methylisoquinoline 4-chlorophenol 4-methoxyindole 4-methylindole 4-methylquinoline 4-nitroindole 5-(propan-2-ylidene)cyclopenta-1,3-diene 5-bromoindole 5-chloroindole 5-cyanoindole 5-fluoroindole 5-methylindole 5-nitroindole 6-chloroindole 6-methoxyindole 6-methylfulvene 6-methylquinoline 6-nitroindole 7-bromoindole 7-chloroindole 7-methylindole 8-methylquinoline acenaphthylene anisole benzo[a]pyrene benzocyclobutene benzocyclohept-1-ene benzofuran benzophenone benzothiophene benzylethylsulfide benzylmethylsulfide Bibenzyl biphenyl carbazole cinnoline cis-Stilbene Cyclohexylbenzene cyclopropylbenzene dibenzo-p-dioxin dibenzofuran dibenzothiophene Diphenylether Diphenylmethane ethyl phenyl sulfide ethylbenzene fluoranthene fluorene i-propylphenylsulfide indan indene indole indoline isochroman isoflavone isoquinoline m-chlorophenylmethylsulfide m-cresol m-nitrotoluene m-terphenyl m-xylene methyl p-nitrophenyl sulfide methyl p-tolyl sulfide methyl phenyl sulfide methyl-2-naphthoate methylthiocyclohexane n-butylphenylsulfide N-methylaniline N-methylindole n-propylphenylsulfide N,N-dimethylaniline norcarane o-bromostyrene o-chlorophenylmethylsulfide o-cresol o-nitrotoluene o-xylene p-bromophenylmethylsulfide p-chlorophenylethylsulfide p-chlorophenylmethylsulfide p-cresol p-cyanophenylmethylsulfide p-fluorophenylmethylsulfide p-methoxyphenyl methyl sulfide p-nitrotoluene p-xylene phenanthrene phenetole phenol phenyl naphthalene phenyl vinyl sulphide phthalazine pyrene quinazoline quinoline spiro[2.4]hepta-4,6-diene spiro[cyclopropane-1,1'-indene] styrene Toluene trans-decalin trans-Stilbene triphenylene triphenylmethane xanthene

Compound	Product	Expression System	Reference
(1R)-indanol	cis-1,3-indandiol	Pseudomonas sp. NCIB 9816-4	+
Lee K, Resnick SM, Gibson DT. Stereospecific oxidation of (R)- and (S)-1-indanol by naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4. Appl Environ Microbiol. 1997 May;63(5):2067-70. PubMed PMID: 9143136
(1R)-indanol	(R)-3-hydroxy-1-indanone	Pseudomonas sp. NCIB 9816-4	+
Lee K, Resnick SM, Gibson DT. Stereospecific oxidation of (R)- and (S)-1-indanol by naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4. Appl Environ Microbiol. 1997 May;63(5):2067-70. PubMed PMID: 9143136
(1S)-indanol	(R)-3-hydroxy-1-indanone	Pseudomonas sp. NCIB 9816-4	+
Lee K, Resnick SM, Gibson DT. Stereospecific oxidation of (R)- and (S)-1-indanol by naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4. Appl Environ Microbiol. 1997 May;63(5):2067-70. PubMed PMID: 9143136
(S)-1-phenethyl alcohol		Pseudomonas sp. NCIB 9816-4	+
Lee K, Gibson DT. Toluene and ethylbenzene oxidation by purified naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4. Appl Environ Microbiol. 1996 Sep;62(9):3101-6. PubMed Central PMCID: PMC168101. PMID: 8795196
[2-(methylsulfanyl)ethyl]benzene		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
1-methylisoquinoline	Isoquinolin-1-ylmethanol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
1-methylisoquinoline	cis-1-methyl-7,8-dihydroisoquinoline-7,8-diol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
1-methylpyridin-2-one	cis-5,6-dihydro-5,6-dihydroxy-1-methyl-2-pyridone	Escherichia coli JM109 pDTG141	+
Modyanova, L., & Azerad, R. (2000). Dioxygenase-catalysed formation of dihydrodiol metabolites of N-methyl-2-pyridone. Tetrahedron Letters, 41(20), 3865–3869. doi: 10.1016/S0040-4039(00)00541-4
1-methylpyridin-2-one	cis-3,4-dihydro-3,4-dihydroxy-1-methyl-2-pyridone	Escherichia coli JM109 pDTG141	+
Modyanova, L., & Azerad, R. (2000). Dioxygenase-catalysed formation of dihydrodiol metabolites of N-methyl-2-pyridone. Tetrahedron Letters, 41(20), 3865–3869. doi: 10.1016/S0040-4039(00)00541-4
1-methylpyridin-2-one	trans-5,6-dihydro-5,6-dihydroxy-1-methyl-2-pyridone	Escherichia coli JM109 pDTG141	+
Modyanova, L., & Azerad, R. (2000). Dioxygenase-catalysed formation of dihydrodiol metabolites of N-methyl-2-pyridone. Tetrahedron Letters, 41(20), 3865–3869. doi: 10.1016/S0040-4039(00)00541-4
1-Phenylethanone	2-Hydroxy-acetophenone	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
1-phenylpyrazole	1-phenylpyrazol-4-ol	Escherichia coli JM109 pDTG141	+
Thawng, C. N. (2011). Biotransformation of N-Heterocyclic Compounds 1-Phenylpyrazole and 1-Phenylpyrrole by Escherichia coli (pDTG141) Expressing Naphthalene Dioxygenase of Pseudomonas sp. Strain NCIB 9816-4. Journal of the Korean Society for Applied Biological Chemistry, 54(2). doi: 10.3839/jksabc.2011.037
1-phenylpyrrole		Escherichia coli JM109 pDTG141	+
Thawng, C. N. (2011). Biotransformation of N-Heterocyclic Compounds 1-Phenylpyrazole and 1-Phenylpyrrole by Escherichia coli (pDTG141) Expressing Naphthalene Dioxygenase of Pseudomonas sp. Strain NCIB 9816-4. Journal of the Korean Society for Applied Biological Chemistry, 54(2). doi: 10.3839/jksabc.2011.037
1,1-diphenylethylene		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
1,2-dihydronaphthalene	(-)-(1R,2S)-cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
1,2,3,4-tetrahydronaphthalene		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
1,2,3,4-tetrahydronaphthalene		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
1,2,3,5,6,7-hexahydro-S-indacene		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
1,3-cycloheptadiene		Pseudomonas sp. NCIB 9816-11	+
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-cyclohexadiene		Pseudomonas sp. NCIB 9816-11	+
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-cyclooctadiene		Pseudomonas sp. NCIB 9816-11	+
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		Pseudomonas sp. NCIB 9816-11	+
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 sp. NCIB 9816-4	+
Catterall GF, Williams PA. Some properties of the naphthalene oxygenase from Pseudomonas sp. NCIB 9816. J Gen Microbiol. 1971 Jul;67(1):117-24. PubMed PMID: PMID: 4330923
1,5-dimethylnaphthalene	1-Naphthalenemethanol, 5-methyl-	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
1,5-dimethylnaphthalene	1,5-Naphthalenedimethanol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
1,5-naphthyridine		Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
1,8-dimethylnaphthalene	1-Naphthalenemethanol, 8-methyl-	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
1,8-dimethylnaphthalene	1,8-Naphthalenedimethanol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
2-bromo naphthalene	7-bromo-1,2-dihydronaphthalene-1,2-diol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
2-chloro naphthalene	7-chloro-1,2-dihydronaphthalene-1,2-diol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
2-chlorophenol		Escherichia coli JM109 pDTG141	+
Lee K. p-hydroxylation reactions catalyzed by naphthalene dioxygenase. FEMS Microbiol Lett. 2006 Feb;255(2):316-20. PMID: 16448512
2-ethyl naphthalene	(1R,2S)-7-ethyl-1,2-dihydronaphthalene-1,2-diol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
2-indanone	(S)-2-Hydroxy-1-indanone	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
2-methyl naphthalene	(1R,2S)-7-methyl-1,2-dihydronaphthalene-1,2-diol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
2-methylbenzothiophene	(+)-2-methyl-cis-4,5-dihydroxy-4,5-dihydrobenzo[b]thiophene	Pseudomonas sp. NCIB 9816-11	+
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
2-methylbenzothiophene	(+)-(1S)-2-Methylbenzo[b]thiophene-1-oxide	Pseudomonas sp. NCIB 9816-11	+
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
2-methylquinoline	cis-2-Methyl-5,6-dihydroquinoline-5,6-diol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
2-methylquinoline	2-methylquinolin-8-ol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
2,6-dimethylnaphthalene	6-methyl-2-naphthalenemethanol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
2,7-dimethylnaphthalene	7-methyl-2-naphthalenemethanol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
2,7-dimethylnaphthalene	2,7-Naphthalenedimethanol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
3-chlorophenol		Escherichia coli JM109 pDTG141	+
Lee K. p-hydroxylation reactions catalyzed by naphthalene dioxygenase. FEMS Microbiol Lett. 2006 Feb;255(2):316-20. PMID: 16448512
3-methylbenzothiophene	(-)-(R)-3-methylbenzo[b]thiophene-1-oxide	Pseudomonas sp. NCIB 9816-11	+
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
3-methylisoquinoline	cis-1-methyl-7,8-dihydroisoquinoline-7,8-diol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
3-methylisoquinoline	3-methylisoquinolin-5-ol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
4-chlorophenol		Escherichia coli JM109 pDTG141	+
Lee K. p-hydroxylation reactions catalyzed by naphthalene dioxygenase. FEMS Microbiol Lett. 2006 Feb;255(2):316-20. PMID: 16448512
4-methoxyindole		Escherichia coli JM109 pDTG141	+
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
4-methylindole		Escherichia coli JM109 pDTG141	+
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
4-methylquinoline	quinolin-4-ylmethanol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
4-nitroindole		Escherichia coli JM109 pDTG141	+
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-(propan-2-ylidene)cyclopenta-1,3-diene	(1R,2S)-5-isopropylidenecyclopent-3-ene-1,2-diol	Pseudomonas sp. NCIB 9816-11	+
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-bromoindole		Escherichia coli JM109 pDTG141	+
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-chloroindole		Escherichia coli JM109 pDTG141	+
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-cyanoindole		Escherichia coli JM109 pDTG141	+
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-fluoroindole		Escherichia coli JM109 pDTG141	+
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-methylindole		Escherichia coli JM109 pDTG141	+
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-nitroindole		Escherichia coli JM109 pDTG141	+
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-chloroindole		Escherichia coli JM109 pDTG141	+
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 JM109 pDTG141	+
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		Pseudomonas sp. NCIB 9816-11	+
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-methylquinoline	6-methylquinolin-3-ol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
6-nitroindole		Escherichia coli JM109 pDTG141	+
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-bromoindole		Escherichia coli JM109 pDTG141	+
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 JM109 pDTG141	+
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-methylindole		Escherichia coli JM109 pDTG141	+
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
8-methylquinoline	quinolin-8-ylmethanol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
8-methylquinoline	cis-8-methyl-5,6-dihydroquinoline-5,6-diol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
acenaphthylene	cis-1,2-acenaphthenediol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
anisole	phenol	Pseudomonas sp. NCIB 9816-11	+
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
benzo[a]pyrene		Pseudomonas sp. NCIB 9816-4	+
Barnsley EA. The bacterial degradation of fluoranthene and benzo[alpyrene. Can J Microbiol. 1975 Jul;21(7):1004-8. PMID: 1148939
benzocyclobutene	Benzocyclobutene-1-ol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
benzocyclohept-1-ene	(5R,6S)-6,7,8,9-Tetrahydro-5H-benzo[7]annulene-5,6-diol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
benzofuran		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
benzophenone		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
benzothiophene	2,3-dihydro-benzo[b]thiophene-2,3-diol	Pseudomonas sp. NCIB 9816-11	+
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 sp. NCIB 9816-11	+
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
benzylethylsulfide		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
benzylmethylsulfide		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
Bibenzyl		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
biphenyl		Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
carbazole	3-hydroxycarbazole	Pseudomonas sp. NCIB 9816-4	+
Resnick SM, Torok DS, Gibson DT. Oxidation of carbazole to 3-hydroxycarbazole by naphthalene 1,2-dioxygenase and biphenyl 2,3-dioxygenase. FEMS Microbiol Lett. 1993 Nov 1;113(3):297-302. PMID: 8270195
cinnoline		Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
cis-Stilbene	cis-3-Phenylcyclohexa-3,5-diene-1,2-diol	Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
Cyclohexylbenzene		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
cyclopropylbenzene		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
dibenzo-p-dioxin	cis-1,2-dihydroxy-1,2-dihydrodibenzo-p-dioxin	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
dibenzofuran	cis-1,2-dihydroxy-1,2-dihydrodibenzofuran	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
dibenzofuran	cis-3,4-Dihydroxy-3,4-dihydrodibenzofuran	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
dibenzothiophene	dibenzothiophene-5-oxide	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
Diphenylether		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
Diphenylmethane		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
ethyl phenyl sulfide	Ethyl phenyl sulfoxide	Pseudomonas sp. NCIB 9816-4	+
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	(S)-1-phenethyl alcohol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
fluoranthene		Pseudomonas sp. NCIB 9816-4	+
Barnsley EA. The bacterial degradation of fluoranthene and benzo[alpyrene. Can J Microbiol. 1975 Jul;21(7):1004-8. PMID: 1148939
fluorene	9-fluorenol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
i-propylphenylsulfide		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
indan	(1S)-indenol	Pseudomonas sp. NCIB 9816-11	+
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
indan	(1S)-indanol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
indan	indene	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
indan	(1S)-indenol	Pseudomonas sp. NCIB 9816-4	+
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 sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
indole		Escherichia coli JM109 pDTG141	+
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
indole	cis-2,3-dihydro-indole-2,3-diol	Pseudomonas sp. NCIB 9816-11	+
Ensley BD, Ratzkin BJ, Osslund TD, Simon MJ, Wackett LP, Gibson DT. Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo. Science. 1983 Oct 14;222(4620):167-9. PMID: 6353574
indoline	indole	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
isochroman		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
isoflavone	3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-4H-chromen-4-one	Escherichia coli JM109 pDTG141	+
Seo J, Kang SI, Ryu JY, Lee YJ, Park KD, Kim M, Won D, Park HY, Ahn JH, Chong Y, Kanaly RA, Han J, Hur HG. Location of flavone B-ring controls regioselectivity and stereoselectivity of naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4. Appl Microbiol Biotechnol. 2010 May;86(5):1451-62. doi: 10.1007/s00253-009-2389-6. PMID: 20091026
isoquinoline	Isoquinolin-5-ol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
isoquinoline	cis-7,8-dihydroisoquinoline-7,8-diol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
isoquinoline	cis-5,6-dihydroisoquinoline-5,6-diol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
isoquinoline	isoquinolin-4-ol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
m-chlorophenylmethylsulfide		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
m-cresol		Escherichia coli JM109 pDTG141	+
Lee K. p-hydroxylation reactions catalyzed by naphthalene dioxygenase. FEMS Microbiol Lett. 2006 Feb;255(2):316-20. PMID: 16448512
m-nitrotoluene	(3-nitrophenyl)methanol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
m-nitrotoluene	3-nitrobenzaldehyde	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
m-terphenyl		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
m-xylene	(3-methylphenyl)methanol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
methyl p-nitrophenyl sulfide	Methyl p-nitrophenyl sulfoxide	Pseudomonas sp. NCIB 9816-4	+
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	Methyl p-tolyl sulfoxide	Pseudomonas sp. NCIB 9816-4	+
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	Methyl phenyl sulfoxide	Pseudomonas sp. NCIB 9816-4	+
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-2-naphthoate	methyl (7S,8R)-7,8-dihydroxy-7,8-dihydronaphthalene-2-carboxylate	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
methylthiocyclohexane		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
n-butylphenylsulfide		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
N-methylaniline	Aniline	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
N-methylindole	indole	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
n-propylphenylsulfide		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
N,N-dimethylaniline	Aniline	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
norcarane	1-cyclohex-2-enylmethanol	Pseudomonas sp. NCIB 9816-4	+
Chakrabarty S, Austin RN, Deng D, Groves JT, Lipscomb JD. Radical intermediates in monooxygenase reactions of rieske dioxygenases. J Am Chem Soc. 2007 Mar 28;129(12):3514-5. PubMed Central PMCID: PMID: 17341076
o-bromostyrene	(1R)-1-(2-bromophenyl)ethan-1,2-diol	Pseudomonas sp. NCIB 9816-11	+
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-chlorophenylmethylsulfide		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
o-cresol		Escherichia coli JM109 pDTG141	+
Lee K. p-hydroxylation reactions catalyzed by naphthalene dioxygenase. FEMS Microbiol Lett. 2006 Feb;255(2):316-20. PMID: 16448512
o-nitrotoluene	(2-Nitrophenyl)methanol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
o-nitrotoluene	styrene	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
o-xylene		Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
p-bromophenylmethylsulfide		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
p-chlorophenylethylsulfide		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
p-chlorophenylmethylsulfide		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
p-cresol		Escherichia coli JM109 pDTG141	+
Lee K. p-hydroxylation reactions catalyzed by naphthalene dioxygenase. FEMS Microbiol Lett. 2006 Feb;255(2):316-20. PMID: 16448512
p-cyanophenylmethylsulfide		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
p-fluorophenylmethylsulfide		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
p-methoxyphenyl methyl sulfide	p-Methoxyphenyl methyl sulfoxide	Pseudomonas sp. NCIB 9816-4	+
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	(4-Nitrophenyl)methanol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
p-nitrotoluene	p-Nitrobenzaldehyde	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
p-xylene	(4-methylphenyl)methanol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
phenanthrene	(1R,2S)-dihydrophenanthrene-1,2-diol	Pseudomonas sp. NCIB 9816-4	+
Ferraro DJ, Okerlund AL, Mowers JC, Ramaswamy S. Structural basis for regioselectivity and stereoselectivity of product formation by naphthalene 1,2-dioxygenase. J Bacteriol. 2006 Oct;188(19):6986-94. PMID: 16980501
phenetole	phenol	Pseudomonas sp. NCIB 9816-11	+
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	ethenyloxybenzene	Pseudomonas sp. NCIB 9816-11	+
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		Escherichia coli JM109 pDTG141	+
Lee K. p-hydroxylation reactions catalyzed by naphthalene dioxygenase. FEMS Microbiol Lett. 2006 Feb;255(2):316-20. PMID: 16448512
phenyl naphthalene		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
phenyl vinyl sulphide		Escherichia coli JM109 pDTG141	+
Kerridge, A., Willetts, A., & Holland, H. (1999). Stereoselective oxidation of sulfides by cloned naphthalene dioxygenase. Journal of Molecular Catalysis B: Enzymatic, 6(1-2), 59–65. doi: 10.1016/S1381-1177(98)00121-0
phthalazine	Phthalazin-5-ol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
pyrene		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
quinazoline	cis-5,6-dihydroquinoxaline-5,6-diol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
quinazoline	quinazolin-8-ol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
quinoline	(5R,6S)-5,6-dihydroquinoline-5,6-diol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
quinoline	quinolin-3-ol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
quinoline	cis-7,8-dihydroquinoline-7,8-diol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
quinoline	quinolin-8-ol	Escherichia coli JM109 pDTG141	+
Chopard, C., Bertho, G., & Prangé, T. (2012). Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes. RSC Adv., 2(2), 605–615. doi: 10.1039/c1ra00706h
spiro[2.4]hepta-4,6-diene		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
spiro[cyclopropane-1,1'-indene]		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
styrene	(1R)-1-phenyl-1,2-ethanediol	Pseudomonas sp. NCIB 9816-4	+
Resnick, S., Lee, K., & Gibson, D. (1996). Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816. Journal of Industrial Microbiology & Biotechnology, 17(5-6), 438–457. doi: 10.1007/BF01574775
Toluene	Benzyl alcohol	Pseudomonas sp. NCIB 9816-4	+
Lee K, Gibson DT. Toluene and ethylbenzene oxidation by purified naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4. Appl Environ Microbiol. 1996 Sep;62(9):3101-6. PubMed Central PMCID: PMC168101. PMID: 8795196
Toluene	Benzaldehyde	Pseudomonas sp. NCIB 9816-4	+
Lee K, Gibson DT. Toluene and ethylbenzene oxidation by purified naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4. Appl Environ Microbiol. 1996 Sep;62(9):3101-6. PubMed Central PMCID: PMC168101. PMID: 8795196
trans-decalin		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
trans-Stilbene		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
triphenylene		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
triphenylmethane		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321
xanthene		Pseudomonas sp. NCIB 9816-4	+
Aukema KG, Kasinkas L, Aksan A, Wackett LP. Use of silica-encapsulated Pseudomonas sp. strain NCIB 9816-4 in biodegradation of novel hydrocarbon ring structures found in hydraulic fracturing waters. Appl Environ Microbiol. 2014 Aug;80(16):4968-76. doi: 10.1128/AEM.01100-14. PubMed PMID: 24907321