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Literature summary extracted from

  • Hlouchova, K.; Rudolph, J.; Pietari, J.M.; Behlen, L.S.; Copley, S.D.
    Pentachlorophenol hydroxylase, a poorly functioning enzyme required for degradation of pentachlorophenol by Sphingobium chlorophenolicum (2012), Biochemistry, 51, 3848-3860.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.13.50 expression in Escherichia coli Sphingobium chlorophenolicum

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.14.13.50 0.001
-
 Pentachlorophenol below 0.001, pH 7.0, 22°C Sphingobium chlorophenolicum
1.14.13.50 0.0056
-
 2,3,5,6-Tetrachlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum
1.14.13.50 0.0126
-
 2,6-dichlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum
1.14.13.50 0.059
-
 3,4,5-trichlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum
1.14.13.50 0.098
-
 3,5-dichlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum

Organism

EC Number Organism UniProt Comment Textmining
1.14.13.50 Sphingobium chlorophenolicum
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.13.50 2,3,5,6-tetrachlorophenol + 2 NADPH + H+ + O2
-
 Sphingobium chlorophenolicum 2,3,5,6-tetrachloro-p-hydroquinone + 2 NADP+ + chloride + H2O
-
 ?
1.14.13.50 2,6-dichlorophenol + NADPH + H+ + O2
-
 Sphingobium chlorophenolicum 2,6-dichloro-p-hydroquinone + NADP+ + H2O
-
 ?
1.14.13.50 3,4,5-trichlorophenol + 2 NADPH + H+ + O2
-
 Sphingobium chlorophenolicum 3,5-dichloro-p-hydroquinone + 2 NADP+ + chloride + H2O
-
 ?
1.14.13.50 3,5-dichlorophenol + NADPH + H+ + O2
-
 Sphingobium chlorophenolicum 3,5-dichloro-p-hydroquinone + NADP+ + H2O
-
 ?
1.14.13.50 additional information 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 Sphingobium chlorophenolicum ?
-
 ?
1.14.13.50 pentachlorophenol + 2 NADPH + H+ + O2
-
 Sphingobium chlorophenolicum tetrachlorobenzoquinone + 2 NADP+ + chloride + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.13.50 PCP hydroxylase
-
 Sphingobium chlorophenolicum
1.14.13.50 pentachlorophenol hydroxylase
-
 Sphingobium chlorophenolicum

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.14.13.50 0.01
-
 3,5-dichlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum
1.14.13.50 0.01
-
 3,4,5-trichlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum
1.14.13.50 0.024
-
 Pentachlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum
1.14.13.50 0.046
-
 2,6-dichlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum
1.14.13.50 0.32
-
 2,3,5,6-Tetrachlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1.14.13.50 0.102
-
 3,5-dichlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum
1.14.13.50 0.169
-
 3,4,5-trichlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum
1.14.13.50 3.81
-
 2,6-dichlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum
1.14.13.50 24
-
 Pentachlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum
1.14.13.50 57
-
 2,3,5,6-Tetrachlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum