1.14.13.50: pentachlorophenol monooxygenase
This is an abbreviated version!
For detailed information about pentachlorophenol monooxygenase, go to the full flat file.
Word Map on EC 1.14.13.50
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1.14.13.50
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pcp-degrading
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flavobacterium
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sphingobium
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chlorophenolicum
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tetrachlorohydroquinone
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bioremediation
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tetrachlorobenzoquinone
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dehalogenation
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environmental protection
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arthrobacter
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degradation
- 1.14.13.50
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pcp-degrading
- flavobacterium
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sphingobium
- chlorophenolicum
- tetrachlorohydroquinone
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bioremediation
- tetrachlorobenzoquinone
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dehalogenation
- environmental protection
- arthrobacter
- degradation
Reaction
Synonyms
CpsB, dechlorinase, pentachlorophenol, GM610_18120, oxygenase, pentachlorophenol 4-mono-, PCB hydroxylase, PCP 4-monooxygenase, PCP hydroxylase, PCP-4-monooxygenase, PCP-monooxygenase, PCP4MO, PcpB, PcpD, pentachlorophenol 4-mono-oxygenase, pentachlorophenol 4-monooxygenase, pentachlorophenol dechlorinase, pentachlorophenol dehalogenase, pentachlorophenol hydroxylase, pentachlorophenol monooxygenase, pentachlorophenol-4-monooxygenase, Phe4MO, tetrachlorobenzoquinone reductase
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Substrates Products
Substrates Products on EC 1.14.13.50 - pentachlorophenol monooxygenase
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REACTION DIAGRAM
2,3,4,5-tetrachlorophenol + NADPH + O2
2,3,5-trichlorohydroquinone + Cl- + NADP+ + H2O
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?
2,3,5,6-tetrachlorophenol + 2 NADPH + H+ + O2
2,3,5,6-tetrachloro-p-hydroquinone + 2 NADP+ + chloride + H2O
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?
2,3,5,6-tetrachlorophenol + NADPH + O2
2,3,5,6-tetrachloro-p-hydroquinone + NADP+
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?
2,3,6-trichlorophenol + NADPH + O2
2,3,6-trichloro-p-hydroquinone + NADP+ + H2O
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?
2,4,6-tribromophenol + NADPH + O2
2,6-dibromo-p-hydroquinone + Br- + NADP+ + H2O
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low activity
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?
2,6-dibromo-4-nitrophenol + NADPH + O2
2,6-dibromo-p-hydroquinone + NO2- + NADP+ + H2O
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low activity
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?
2,6-dibromophenol + NADPH + O2
2,6-dibromo-p-hydroquinone + NADP+ + H2O
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?
2,6-dichlorophenol + NADPH + H+ + O2
2,6-dichloro-p-hydroquinone + NADP+ + H2O
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?
2,6-dichlorophenol + NADPH + O2
2,6-dichloro-p-hydroquinone + NADP+ + H2O
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?
3,4,5-trichlorophenol + 2 NADPH + H+ + O2
3,5-dichloro-p-hydroquinone + 2 NADP+ + chloride + H2O
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?
3,5-dibromo-4-hydroxybenzonitrile + 2 NADPH + 2 H+ + O2
2,6-dibromo-p-hydroquinone + CN- + 2 NADP+ + H2O
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?
3,5-dichlorophenol + NADPH + H+ + O2
3,5-dichloro-p-hydroquinone + NADP+ + H2O
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?
4-amino-2,6-dichlorophenol + NADPH + O2
2,6-dichloro-p-hydroquinone + NADP+ + NH2OH
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low activity
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?
pentachlorophenol + 2 NADPH + H+ + O2
tetrachlorobenzoquinone + 2 NADP+ + chloride + H2O
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?
pentachlorophenol + 2 NADPH + H+ + O2
tetrachlorohydroquinone + 2 NADP+ + chloride + H2O
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product is not tetrachlorobenzoquinone as previously thought, ethyl acetate and glutathione can shift the redox-equilibrium in favor of tetrachlorobenzoquinone, room temperature (23-25°C), 50 mM phosphate buffer, pH 7.0, while with NADPH tetrachlorobenzoquinone is reduced to tetrachlorohydroquinone (with 0.5-1 mol NADPH/mol tetrachlorobenzoquinone 50-65% are reduced, with 2.5 mol or more almost complete reduction occurs), deionized distilled water, pH 6.8 (due to interference of phosphate or Tris-HCl buffer with the detection of tetrachlorohydroquinone)
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?
pentachlorophenol + NADH + H+ + O2
2,3,5,6-tetrachloro-1,4-benzoquinone + NAD+ + chloride + H2O
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r
pentachlorophenol + NADH + H+ + O2
2,3,5,6-tetrachloro-1,4-benzoquinone + NADP+ + chloride + H2O
pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachloro-1,4-benzoquinone + NADP+ + chloride + H2O
pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
2,6-dichloro-p-hydroquinone + Cl- + NADP+ + H2O
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?
2,4,6-trichlorophenol + NADPH + O2
2,6-dichloro-p-hydroquinone + Cl- + NADP+ + H2O
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low activity
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?
tetrachlorohydroquinone + 2 NADP+ + Cl- + H2O
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pentachlorophenol + 2 NADPH + H+ + O2
tetrachlorohydroquinone + 2 NADP+ + Cl- + H2O
wild-type and transformed E. coli cells
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?
pentachlorophenol + 2 NADPH + H+ + O2
tetrachlorohydroquinone + 2 NADP+ + Cl- + H2O
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solitary oxygenolytic pathway for removal of the primary chlorine during PCP degradation, not a hydrolytic one
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?
pentachlorophenol + 2 NADPH + H+ + O2
tetrachlorohydroquinone + 2 NADP+ + Cl- + H2O
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wild-type and mutant strains
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?
2,3,5,6-tetrachloro-1,4-benzoquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADH + H+ + O2
2,3,5,6-tetrachloro-1,4-benzoquinone + NADP+ + chloride + H2O
Bacillus tropicus AOA-CPS1
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2,3,5,6-tetrachloro-1,4-benzoquinone + NADP+ + chloride + H2O
degradation of pentachlorophenol
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachloro-1,4-benzoquinone + NADP+ + chloride + H2O
the enzyme is an unusually slow flavin-dependent monooxygenase (kcat = 0.02/s) that converts pentachlorophenol to a highly reactive product, tetrachlorobenzoquinone. By stopped-flow spectroscopy, it is shown that the steps up to and including formation of tetrachlorobenzoquinone are rapid (5-30/s). Before products can be released from the active site, the strongly oxidizing tetrachlorobenzoquinone abstracts an electron from a donor at the active site, possibly a cysteine residue, resulting in an off-pathway diradical state that only slowly reverts to an intermediate capable of completing the catalytic cycle
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2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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oxygen and NADPH are essential
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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initial enzyme in the PCP catabolic pathway of numerous sphingomonads, PCP-4-monooxygenase (PcpB), catalyzes the parahydroxylation of PCP to tetrachlorohydroquinone, pentachlorophenol degradation pathway, overview
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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initial enzyme in the PCP catabolic pathway of numerous sphingomonads, PCP-4-monooxygenase (PcpB), catalyzes the parahydroxylation of PCP to tetrachlorohydroquinone, pentachlorophenol degradation pathway, overview
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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initial enzyme in the PCP catabolic pathway of numerous sphingomonads, PCP-4-monooxygenase (PcpB), catalyzes the parahydroxylation of PCP to tetrachlorohydroquinone, pentachlorophenol degradation pathway, overview
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pentachlorophenol + NADPH + H+ + O2
2,3,5,6-tetrachlorohydroquinone + NADP+ + chloride + H2O
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tetrachlorobenzoquinone + NADP+ + chloride + H2O
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ir
pentachlorophenol + NADPH + H+ + O2
tetrachlorobenzoquinone + NADP+ + chloride + H2O
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first step of pentachlorophenol degradation pathway
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ir
tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol degradation
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pentachlorophenol + NADPH + H+ + O2
tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2
tetrachlorohydroquinone + NADP+ + chloride + H2O
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pentachlorophenol degradation
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tetrachlorohydroquinone + NADP+
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tetrachlorobenzoquinone + NADPH
tetrachlorohydroquinone + NADP+
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second step in pentachlorophenol degradation, physiological role in association with pentachloro monooxygenase, overview
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diiodohydroquinone + iodide + NADP+ + H2O
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triiodophenol + NADPH + O2
diiodohydroquinone + iodide + NADP+ + H2O
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no activity with 3,4,5-trichlorophenol, 2,4-dichlorophenol, 3,4-dichlorophenol, 4-chlorophenol
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additional information
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enzyme CpsB from Bacillus tropicus reacts with PCP to trap 1,4-tetrachlorobenzoquinone (Tet-CBQ) formed as 2,3,5,6-tetrakis[(2-hydroxyethyl)thio]-1,4-hydroquinone (THTH)
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additional information
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Bacillus tropicus AOA-CPS1
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enzyme CpsB from Bacillus tropicus reacts with PCP to trap 1,4-tetrachlorobenzoquinone (Tet-CBQ) formed as 2,3,5,6-tetrakis[(2-hydroxyethyl)thio]-1,4-hydroquinone (THTH)
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additional information
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broad substrate specificity, hydroxylation in para-position
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additional information
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enzyme also removes amino, cyano and nitro groups from the para-position to the hydroxyl group of the phenol
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additional information
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enzyme also removes amino, cyano and nitro groups from the para-position to the hydroxyl group of the phenol
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additional information
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overview: enzyme catalyzes a primary attack on a broad range of substituted phenols, hydroxylating the para position and removing halogen, nitro, amino and cyano groups to produce halide, nitrite, hydroxylamine and cyanide respectively
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additional information
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no activity with 3,4,5-trichlorophenol, 3,5-dichlorophenol
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additional information
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broad substrate and catalytic reaction range
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additional information
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biodegradation of the herbicide bromoxynil, i.e. 3,5-dibromo-4-hydroxybenzonitrile
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additional information
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lateral gene transfer and the origin of the pentachlorophenol pathway, overview
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additional information
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enzyme expression in response to pentachlorophenol hydroxylase PcpB
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additional information
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lateral gene transfer and the origin of the pentachlorophenol pathway, overview
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additional information
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enzyme exhibits substantial uncoupling. The C4a-hydroxyflavin intermediate, instead of hydroxylating the substrate, can decompose to produce H2O2 in a futile cycle that consumes NADPH. The extent of uncoupling varies from 0 to 100% with different substrates. The extent of uncoupling is increased by the presence of bulky substituents at position 3, 4, or 5 and decreased by the presence of a chlorine in the ortho position. The effectiveness of pentachlorophenol hydroxylase is additionally hindered by its promiscuous activity with tetrachlorohydroquinone, a downstream metabolite in the degradation pathway. The conversion of tetrachlorohydroquinone to tetrachlorobenzoquinone reverses flux through the pathway. Substantial uncoupling also occurs during the reaction with tetrachlorohydroquinone
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additional information
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broad substrate specificity, hydroxylation in para-position
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additional information
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lateral gene transfer and the origin of the pentachlorophenol pathway, overview
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?
additional information
?
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broad substrate specificity, hydroxylation in para-position
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