1.14.13.7: phenol 2-monooxygenase (NADPH)
This is an abbreviated version!
For detailed information about phenol 2-monooxygenase (NADPH), go to the full flat file.
Word Map on EC 1.14.13.7
-
1.14.13.7
-
catechols
-
phenol-degrading
-
hydroxylases
-
2,3-dioxygenase
-
trichosporon
-
cutaneum
-
meta-cleavage
-
diiron
-
cresol
-
comamonas
-
2-hydroxymuconic
-
testosteroni
-
haldane
-
coke
-
radioresistens
-
carboxylate-bridged
-
meta-pathway
-
ortho-cleavage
-
methylococcus
-
cis,cis-muconate
-
coking
-
environmental protection
-
industry
-
synthesis
-
degradation
- 1.14.13.7
- catechols
-
phenol-degrading
- hydroxylases
-
2,3-dioxygenase
- trichosporon
- cutaneum
-
meta-cleavage
-
diiron
- cresol
- comamonas
-
2-hydroxymuconic
- testosteroni
-
haldane
-
coke
- radioresistens
-
carboxylate-bridged
-
meta-pathway
-
ortho-cleavage
-
methylococcus
- cis,cis-muconate
-
coking
- environmental protection
- industry
- synthesis
- degradation
Reaction
Synonyms
DmpLNO, flavin containing monooxygenase, LmPH, Mph, MphN, multi-component phenol hydroxylase, multicomponent PH, multicomponent phenol hydroxylase, multicomponent phenol hydroxylase alpha subunit, NCgl2588, oxygenase, phenol 2-mono-, PHE, phenol hydroxylase, phenol o-hydroxylase, PHH, phhY, PHIND, PHO, PHR, single-component PH, SPH
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Reference on EC 1.14.13.7 - phenol 2-monooxygenase (NADPH)
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REF. 
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Krug, M.; Straube, G.
Degradation of phenolic compounds by the yeast Candida tropicalis HP 15. II. Some properties of the first two enzymes of the degradation pathway
J. Basic Microbiol.
26
271-281
1986
Candida tropicalis
Neujahr, H.Y.; Gaal, A.
Phenol hydroxylase from yeast. Purification and properties of the enzyme from Trichosporon cutaneum
Eur. J. Biochem.
35
386-400
1973
Cutaneotrichosporon cutaneum
Nakagawa, H.; Takeda, Y.
Phenol hydroxylase
Biochim. Biophys. Acta
62
423-426
1962
Brevibacterium fuscum
Neujahr, H.Y.; Gaal, A.
Phenol hydroxylase from yeast. Sulfhydryl groups in phenol hydroxylase from Trichosporon cutaneum
Eur. J. Biochem.
58
351-357
1975
Cutaneotrichosporon cutaneum
Kjellen, K.G.; Neujahr, H.Y.
Immobilization of phenol hydroxylase
Biotechnol. Bioeng.
21
715-719
1979
Cutaneotrichosporon cutaneum
Detmer, K.; Massey, V.
Effect of monovalent anions on the mechanism of phenol hydroxylase
J. Biol. Chem.
259
11265-11272
1984
Cutaneotrichosporon cutaneum
Detmer, K.; Massey, V.
Effect of substrate and pH on the oxidative half-reaction of phenol hydroxylase
J. Biol. Chem.
260
5998-6005
1985
Cutaneotrichosporon cutaneum
Neujahr, H.Y.; Kjellen, K.G.
Phenol hydroxylase from yeast. Reaction with phenol derivatives
J. Biol. Chem.
253
8835-8841
1978
Cutaneotrichosporon cutaneum
Neujahr, H.Y.
Effect of anions, chaotropes, and phenol on the attachment of flavin adenine dinucleotide to phenol hydroxylase
Biochemistry
22
580-584
1983
Cutaneotrichosporon cutaneum
Neujahr, H.Y.; Kjellen, K.G.
Phenol hydroxylase from yeast: a lysyl residue essential for binding of reduced nicotinamide adenine dinucleotide phosphate
Biochemistry
19
4967-4972
1980
Cutaneotrichosporon cutaneum
Selitz, T.; Neujahr, H.Y.
Phenol hydroxylase from yeast. A model for phenol binding and an improved purification procedure
Eur. J. Biochem.
170
343-349
1987
Cutaneotrichosporon cutaneum
Mörtberg, M.; Neujahr, H.Y.
In situ and in vitro kinetics of phenol hydroxylase
Biochem. Biophys. Res. Commun.
146
41-46
1987
Cutaneotrichosporon cutaneum
Cadieux, E.; Vrajmasu, V.; Achim, C.; Powlowski, J.; Muenck, E.
Biochemical, Mossbauer, and EPR studies of the diiron cluster of phenol hydroxylase from Pseudomonas sp. strain CF 600
Biochemistry
41
10680-10691
2002
Pseudomonas sp., Pseudomonas sp. CF 600
Enroth, C.; Neujahr, H.; Schneider, G.; Lindqvist, Y.
The crystal structure of phenol hydroxylase in complex with FAD and phenol provides evidence for a concerted conformational change in the enzyme and its cofactor during catalysis
Structure
6
605-617
1998
Cutaneotrichosporon cutaneum
Hino, S.; Watanabe, K.; Takahashi, N.
Phenol hydroxylase cloned from Ralstonia eutropha strain E2 exhibits novel kinetic properties
Microbiology
144
1765-1772
1998
Cupriavidus necator, Cupriavidus necator E2
-
Kaelin, M.; Neujahr, H.Y.; Weissmahr, R.N.; Sejlitz, T.; Joehl, R.; Fiechter, A.; Reiser, J.
Phenol hydroxylase from Trichosporon cutaneum: gene cloning, sequence analysis, and functional expression in Escherichia coli
J. Bacteriol.
174
7112-7120
1992
Cutaneotrichosporon cutaneum
Maeda-Yorita, K.; Massey, V.
On the reaction mechanism of phenol hydroxylase. New information obtained by correlation of fluorescence and absorbance stopped flow studies
J. Biol. Chem.
268
4134-4144
1993
Cutaneotrichosporon cutaneum
Peelen, S.; Rietjens, I.M.C.M.; Boersma, M.G.; Vervoort, J.
Conversion of phenol derivatives to hydroxylated products by phenol hydroxylase from Trichosporon cutaneum. A comparison of regioselectivity and rate of conversion with calculated molecular orbital substrate characteristics
Eur. J. Biochem.
227
284-291
1995
Cutaneotrichosporon cutaneum
Peelen, S.; Rietjens, I.M.C.M.; van Berkel, W.J.H.; van Workum, W.A.T.; Vervoort, J.
Fluorine-19 NMR study on the pH-dependent regioselectivity and rate of the ortho-hydroxylation of 3-fluorophenol by phenol hydroxylase from Trichosporon cutaneum. Implications for the reaction mechanism
Eur. J. Biochem.
218
345-353
1993
Cutaneotrichosporon cutaneum
Pessione, E.; Divari, S.; Griva, E.; Cavaletto, M.; Rossi, G.L.; Gilardi, G.; Giunta, C.
Phenol hydroxylase from Acinetobacter radioresistens is a multicomponent enzyme. Purification and characterization of the reductase moiety
Eur. J. Biochem.
265
549-555
1999
Acinetobacter radioresistens
Waters, S.; Neujahr, H.Y.
A fermentor culture for production of recombinant phenol hydroxylase
Protein Expr. Purif.
5
534-540
1994
Cutaneotrichosporon cutaneum
Waters, S.; Neujahr, H.Y.
Sources and nature of heterogeneity in recombinant phenol hydroxylase derived from the basidiomycetous soil yeast Trichosporon cutaneum
Biotechnol. Appl. Biochem.
25
235-242
1997
Cutaneotrichosporon cutaneum
-
Xu, D.; Ballou, D.P.; Massey, V.
Studies of the mechanism of phenol hydroxylase: mutants Tyr289Phe, Asp54Asn, and Arg281Met
Biochemistry
40
12369-12378
2001
Cutaneotrichosporon cutaneum
Xu, D.; Enroth, C.; Lindqvist, Y.; Ballou, D.P.; Massey, V.
Studies of the mechanism of phenol hydroxylase: Effect of mutation of proline 364 to serine
Biochemistry
41
13627-13636
2002
Cutaneotrichosporon cutaneum
Enroth, C.
High-resolution structure of phenol hydroxylase and correction of sequence errors
Acta Crystallogr. Sect. D
59
1597-1602
2003
Cutaneotrichosporon cutaneum
Cafaro, V.; Izzo, V.; Scognamiglio, R.; Notomista, E.; Capasso, P.; Casbarra, A.; Pucci, P.; Di Donato, A.
Phenol hydroxylase and toluene/o-xylene monooxygenase from Pseudomonas stutzeri OX1: interplay between two enzymes
Appl. Environ. Microbiol.
70
2211-2219
2004
Pseudomonas stutzeri, Pseudomonas stutzeri OX1
Alexievaa, Z.; Gerginova, M.; Zlateva, P.; Peneva, N.
Comparison of growth kinetics and phenol metabolizing enzymes of Trichosporon cutaneum R57 and mutants with modified degradation abilities
Enzyme Microb. Technol.
34
242-247
2004
Cutaneotrichosporon cutaneum
-
Griva, E.; Pessione, E.; Divari, S.; Valetti, F.; Cavaletto, M.; Rossi, G.L.; Giunta, C.
Phenol hydroxylase from Acinetobacter radioresistens S13. Isolation and characterization of the regulatory component
Eur. J. Biochem.
270
1434-1440
2003
Acinetobacter radioresistens, Acinetobacter radioresistens S13
Divari, S.; Valetti, F.; Caposio, P.; Pessione, E.; Cavaletto, M.; Griva, E.; Gribaudo, G.; Gilardi, G.; Giunta, C.
The oxygenase component of phenol hydroxylase from Acinetobacter radioresistens S13
Eur. J. Biochem.
270
2244-2253
2003
Acinetobacter radioresistens, Acinetobacter radioresistens S13
Stiborova, M.; Sucha, V.; Miksanova, M.; Paca, J.Jr.; Paca, J.
Hydroxylation of phenol to catechol by Candida tropicalis: involvement of cytochrome P450
Gen. Physiol. Biophys.
22
167-179
2003
Candida tropicalis
Jeong, J.J.; Kim, J.H.; Kim, C.K.; Hwang, I.; Lee, K.
3- and 4-alkylphenol degradation pathway in Pseudomonas sp. strain KL28: genetic organization of the lap gene cluster and substrate specificities of phenol hydroxylase and catechol 2,3-dioxygenase
Microbiology
149
3265-3277
2003
Pseudomonas sp., Pseudomonas sp. KL28
Ahuatzi-Chacon, D.; Ordorica-Morales, G.; Ruiz-Ordaz, N.; Cristiani-Urbina, E.; Juarez-Ramirez, C.; Galindez-Mayer, J.
Kinetic study of phenol hydroxylase and catechol 1,2-dioxygenase dioxygenase biosynthesis by Candida tropicalis cells grown on different phenolic substrates.
World J. Microbiol. Biotechnol.
20
695-702
2004
Candida tropicalis
Teramoto, M.; Futamata, H.; Harayama, S.; Watanabe, K.
Characterization of a high-affinity phenol hydroxylase from Comamonas testosteroni R5 by gene cloning, and expression in Pseudomonas aeruginosa PAO1c
Mol. Gen. Genet.
262
552-558
1999
Comamonas testosteroni, Comamonas testosteroni R5
Cafaro, V.; Notomista, E.; Capasso, P.; Di Donato, A.
Regiospecificity of two multicomponent monooxygenases from Pseudomonas stutzeri OX1: molecular basis for catabolic adaptation of this microorganism to methylated aromatic compounds
Appl. Environ. Microbiol.
71
4736-4743
2005
Pseudomonas stutzeri, Pseudomonas stutzeri OX1
Cafaro, V.; Notomista, E.; Capasso, P.; Di Donato, A.
Mutation of glutamic acid 103 of toluene o-xylene monooxygenase as a means to control the catabolic efficiency of a recombinant upper pathway for degradation of methylated aromatic compounds
Appl. Environ. Microbiol.
71
4744-4750
2005
Pseudomonas stutzeri, Pseudomonas stutzeri OX1
Kagle, J.; Hay, A.G.
Phenylacetylene reversibly inhibits the phenol hydroxylase of Pseudomonas sp. CF600 at high concentrations but is oxidized at lower concentrations
Appl. Microbiol. Biotechnol.
72
306-315
2006
Pseudomonas sp., Pseudomonas sp. CF 600
Merimaa, M.; Heinaru, E.; Liivak, M.; Vedler, E.; Heinaru, A.
Grouping of phenol hydroxylase and catechol 2,3-dioxygenase genes among phenol- and p-cresol-degrading Pseudomonas species and biotypes
Arch. Microbiol.
186
287-296
2006
Pseudomonas sp.
Sazinsky, M.H.; Dunten, P.W.; McCormick, M.S.; Didonato, A.; Lippard, S.J.
X-ray structure of a hydroxylase-regulatory protein complex from a hydrocarbon-oxidizing multicomponent monooxygenase, Pseudomonas sp. OX1 phenol hydroxylase
Biochemistry
45
15392-15404
2006
Pseudomonas sp., Pseudomonas sp. OX1
Tsai, S.C.; Tsai, L.D.; Li, Y.K.
An isolated Candida albicans TL3 capable of degrading phenol at large concentration
Biosci. Biotechnol. Biochem.
69
2358-2367
2005
Candida albicans, Candida albicans TL3
Kim, J.Y.; Kim, J.K.; Lee, S.O.; Kim, C.K.; Lee, K.
Multicomponent phenol hydroxylase-catalysed formation of hydroxyindoles and dyestuffs from indole and its derivatives
Lett. Appl. Microbiol.
41
163-168
2005
Pseudomonas sp.
Viggor, S.; Heinaru, E.; Kuennapas, A.; Heinaru, A.
Evaluation of different phenol hydroxylase-possessing phenol-degrading pseudomonads by kinetic parameters
Biodegradation
19
759-769
2008
Pseudomonas putida, Pseudomonas fluorescens, Pseudomonas mendocina
Gerginova, M.; Manasiev, J.; Shivarova, N.; Alexieva, Z.
Influence of various phenolic compounds on phenol hydroxylase activity of a Trichosporon cutaneum strain
Z. Naturforsch. C
62
83-86
2007
Cutaneotrichosporon cutaneum, Cutaneotrichosporon cutaneum R57
Manasiev, J.; Gerginova, M.; Yemendzhiev, H.; Peneva, N.; Alexieva, Z.
Molecular analysis of phenol-degrading microbial strains
Z. Naturforsch. C
63
133-138
2008
no activity in Escherichia coli, no activity in Lactobacillus acidophilus, Cutaneotrichosporon cutaneum, no activity in Escherichia coli JM109
Zhu, C.; Zhang, L.; Zhao, L.
Molecular cloning, genetic organization of gene cluster encoding phenol hydroxylase and catechol 2,3-dioxygenase in Alcaligenes faecalis IS-46
World J. Microbiol. Biotechnol.
24
1687-1695
2008
Alcaligenes faecalis, Alcaligenes faecalis (A5HMH6), Alcaligenes faecalis (A5HMH7), Alcaligenes faecalis (A5HMH8), Alcaligenes faecalis (A5HMH9), Alcaligenes faecalis (A5HMI0), Alcaligenes faecalis (A5HMI1), Alcaligenes sp. IS-46 (Q6V9W5), Alcaligenes faecalis IS-67, Alcaligenes faecalis IS-46 (A5HMH6), Alcaligenes faecalis IS-46 (A5HMH7), Alcaligenes faecalis IS-46 (A5HMH8), Alcaligenes faecalis IS-46 (A5HMH9), Alcaligenes faecalis IS-46 (A5HMI0), Alcaligenes faecalis IS-46 (A5HMI1)
Basile, L.A.; Erijman, L.
Quantitative assessment of phenol hydroxylase diversity in bioreactors using a functional gene analysis
Appl. Microbiol. Biotechnol.
78
863-872
2008
uncultured microorganism (A5YUW2), uncultured microorganism (A5YUW3), uncultured microorganism (A5YUW6), uncultured microorganism (A5YUY2), uncultured microorganism (A5YUY5), uncultured microorganism (A5YUY6), uncultured microorganism (A5YUY7), uncultured microorganism (A5YUZ3), uncultured microorganism (A5YUZ5), uncultured microorganism (A5YUZ6), uncultured microorganism (A5YUZ7), uncultured microorganism (A5YUZ8), uncultured microorganism (A5YUZ9), uncultured microorganism (A5YV00), uncultured microorganism (A5YV01), uncultured microorganism (A5YV02), uncultured microorganism (A5YV03), uncultured microorganism (A5YV04), uncultured microorganism (A5YV05), uncultured microorganism (A5YV06), uncultured microorganism (A5YV08), uncultured microorganism (A5YV10), uncultured microorganism (A5YV11), uncultured microorganism (A5YV12), uncultured microorganism (A5YV13), uncultured microorganism (A5YV14), uncultured microorganism (A5YV15), uncultured microorganism (A5YV16), uncultured microorganism (A5YV18), uncultured microorganism (A5YV19), uncultured microorganism (A5YV20)
Zhan, Y.; Yu, H.; Yan, Y.; Ping, S.; Lu, W.; Zhang, W.; Chen, M.; Lin, M.
Benzoate catabolite repression of the phenol degradation in Acinetobacter calcoaceticus PHEA-2
Curr. Microbiol.
59
368-373
2009
Acinetobacter calcoaceticus
Nebe, J.; Baldwin, B.; Kassab, R.; Nies, L.; Nakatsu, C.
Quantification of aromatic oxygenase genes to evaluate enhanced bioremediation by oxygen releasing materials at a gasoline-contaminated site
Environ. Sci. Technol.
43
2029-2034
2009
uncultured microorganism
Dong, X.; Hong, Q.; He, L.; Jiang, X.; Li, S.
Characterization of phenol-degrading bacterial strains isolated from natural soil
Int. Biodeter. Biodegrad.
62
257-262
2008
Acinetobacter sp. PND-4 (A5Z0R4), Acinetobacter sp. PND-5 (A5Z0R5), Pseudomonas sp. PND-1 (A7L9S7), Pseudomonas sp. PND-2 (A7L9S8), Comamonas sp. PND-3 (A7L9S9), Cupriavidus sp. PND-6 (A7L9T0)
-
Yemendzhiev, H.; Gerginova, M.; Krastanov, A.; Stoilova, I.; Alexieva, Z.
Growth of Trametes versicolor on phenol
J. Ind. Microbiol. Biotechnol.
35
1309-1312
2008
Trametes versicolor, Trametes versicolor 1
Izzo, V.; Leo, G.; Scognamiglio, R.; Troncone, L.; Birolo, L.; Di Donato, A.
PHK from phenol hydroxylase of Pseudomonas sp. OX1. Insight into the role of an accessory protein in bacterial multicomponent monooxygenases
Arch. Biochem. Biophys.
505
48-59
2011
Pseudomonas sp., Pseudomonas sp. OX1
Ma, F.; Shi, S.N.; Sun, T.H.; Li, A.; Zhou, J.T.; Qu, Y.Y.
Biotransformation of benzene and toluene to catechols by phenol hydroxylase from Arthrobacter sp. W1
Appl. Microbiol. Biotechnol.
97
5097-5103
2013
Arthrobacter sp.
McCormick, M.S.; Lippard, S.J.
Analysis of substrate access to active sites in bacterial multicomponent monooxygenase hydroxylases: X-ray crystal structure of xenon-pressurized phenol hydroxylase from Pseudomonas sp. OX1
Biochemistry
50
11058-11069
2011
Pseudomonas sp., Pseudomonas sp. OX1
Tinberg, C.E.; Song, W.J.; Izzo, V.; Lippard, S.J.
Multiple roles of component proteins in bacterial multicomponent monooxygenases: phenol hydroxylase and toluene/o-xylene monooxygenase from Pseudomonas sp. OX1
Biochemistry
50
1788-1798
2011
Pseudomonas sp., Pseudomonas sp. OX1
Turek, M.; Vilimkova, L.; Kremlackova, V.; Paca Jr., J.; Halecky, M.; Paca, J.; Stiborova, M.
Isolation and partial characterization of extracellular NADPH-dependent phenol hydroxylase oxidizing phenol to catechol in Comamonas testosteroni
Neuroendocrinol. Lett.
32
137-145
2011
Comamonas testosteroni
Szoekoel, J.; Rucka, L.; Simcikova, M.; Halada, P.; Nesvera, J.; Patek, M.
Induction and carbon catabolite repression of phenol degradation genes in Rhodococcus erythropolis and Rhodococcus jostii
Appl. Microbiol. Biotechnol.
98
8267-8279
2014
Rhodococcus erythropolis, Rhodococcus jostii, Rhodococcus erythropolis CCM2595
Shi, S.; Qu, Y.; Tan, L.; Ma, F.
Biosynthesis of 1,2-dihydroxydibenzofuran by magnetically immobilized cells of Escherichia coli expressing phenol hydroxylase in liquid-liquid biphasic systems
Biores. Technol.
197
72-78
2015
Arthrobacter sp. W1
Long, Y.; Yang, S.; Xie, Z.; Cheng, L.
Identification and characterization of phenol hydroxylase from phenol-degrading Candida tropicalis strain JH8
Can. J. Microbiol.
60
585-591
2014
Candida tropicalis, Candida tropicalis JH8
Das, B.; Patra, S.
Multisubstrate specific flavin containing monooxygenase from Chlorella pyrenoidosa with potential application for phenolic wastewater remediation and biosensor application
Environ. Technol.
39
2073-2089
2017
Auxenochlorella pyrenoidosa
Shi, S.; Ma, F.; Sun, T.; Li, A.; Zhou, J.; Qu, Y.
Multistep conversion of cresols by phenol hydroxylase and 2,3-dihydroxy-biphenyl 1,2-dioxygenase
Front. Environ. Sci. Eng.
8
539-546
2014
Pseudomonas sp., Pseudomonas sp. OX1
-
Xiao, X.; Si, M.; Yang, Z.; Zhang, Y.; Guan, J.; Chaudhry, M.T.; Wang, Y.; Shen, X.
Molecular characterization of a eukaryotic-like phenol hydroxylase from Corynebacterium glutamicum
J. Gen. Appl. Microbiol.
61
99-107
2015
Corynebacterium glutamicum
El-Sayed, W.S.; Ibrahim, M.K.; Ouf, S.A.
Molecular characterization of the alpha subunit of multicomponent phenol hydroxylase from 4-chlorophenol-degrading Pseudomonas sp. strain PT3
J. Microbiol.
52
13-19
2014
Pseudomonas sp. PT3 (A0A060N2T5)
Das, B.; Patra, S.
Multisubstrate specific flavin containing monooxygenase from Chlorella pyrenoidosa with potential application for phenolic wastewater remediation and biosensor application
Environ. Technol.
39
2073-2089
2018
Auxenochlorella pyrenoidosa, Auxenochlorella pyrenoidosa NCIM 2738
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