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Literature summary for 1.13.11.66 extracted from

  • Machonkin, T.E.; Doerner, A.E.
    Substrate specificity of Sphingobium chlorophenolicum 2,6-dichlorohydroquinone 1,2-dioxygenase (2011), Biochemistry, 50, 8899-8913.
    View publication on PubMed
Search for more literature for 1.13.11.66

Inhibitors

Inhibitors Comment Organism Structure
2,6-dibromophenol competitive Sphingobium chlorophenolicum
3-bromocatechol inactivation Sphingobium chlorophenolicum
ortho-disubstituted phenols
-
 Sphingobium chlorophenolicum

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0013
-
 2,6-dibromohydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum
0.0032
-
 2,6-dichlorohydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum
0.0044
-
 2-chloro-6-methylhydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum
0.0085
-
 bromohydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum
0.01
-
 chlorohydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum
0.021
-
 O2 cosubstrate 2-chloro-6-methylhydroquinone, 1,2-cleavage, pH 7.0, 23°C Sphingobium chlorophenolicum
0.041
-
 methylhydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum
0.055
-
 2,6-dimethylhydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum
0.07
-
 O2 cosubstrate 2,6-dimethylhydroquinone, pH 7.0, 23°C Sphingobium chlorophenolicum
0.12
-
 O2 cosubstrate 2,6-dibromohydroquinone, pH 7.0, 23°C Sphingobium chlorophenolicum
0.19
-
 O2 cosubstrate 2,6-dichlorohydroquinone, pH 7.0, 23°C Sphingobium chlorophenolicum
0.26
-
 O2 cosubstrate 2-chloro-6-methylhydroquinone, 1,6-cleavage, pH 7.0, 23°C Sphingobium chlorophenolicum

Organism

Organism UniProt Comment Textmining
Sphingobium chlorophenolicum Q9ZBB0
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2,6-dibromohydroquinone + O2
-
 Sphingobium chlorophenolicum 2-bromomaleylacetate + Br-
-
 ?
2,6-dichlorohydroquinone + O2 complete conversion of substrate Sphingobium chlorophenolicum 2-chloromaleylacetate + Cl-
-
 ?
2,6-dimethylhydroquinone + O2
-
 Sphingobium chlorophenolicum 2-methylmaleylacetone + ?
-
 ?
2-chloro-6-methylhydroquinone
-
 Sphingobium chlorophenolicum ? complete conversion of substrate, yields a mixture of 1,2- and 1,6-cleavage products. The two modes of cleavage have different Km values for oxygen, consistent with a mechanism in which the substrate binds in two catalytically productive orientations ?
bromohydroquinone + O2
-
 Sphingobium chlorophenolicum maleylacetate + Br-
-
 ?
chlorohydroquinone + O2
-
 Sphingobium chlorophenolicum maleylacetate + Cl-
-
 ?
methylhydroquinone + O2
-
 Sphingobium chlorophenolicum maleylacetone + ?
-
 ?
additional information exhibits a high degree of substrate specificity for 2,6-disubstituted hydroquinones, with halogens greatly preferred at those positions. The asymmetric substrate 2-chloro-6-methylhydroquinone yields a mixture of 87% 1,2-cleavage and 13% 1,6-cleavage products with different Km values for oxygen, consistent with a mechanism in which the substrate binds in two catalytically productive orientations. Monosubstituted hydroquinones show a limited amount of ring cleavage but rapidly inactivate the enzyme in an O2-dependent fashion, suggesting that oxidation of the Fe(II) may be the cause Sphingobium chlorophenolicum ?
-
 ?

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.25
-
 2,6-dimethylhydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum
1.4
-
 O2 cosubstrate 2,6-dimethylhydroquinone, pH 7.0, 23°C Sphingobium chlorophenolicum
1.6
-
 O2 cosubstrate 2-chloro-6-methylhydroquinone, 1,2-cleavage, pH 7.0, 23°C Sphingobium chlorophenolicum
1.61
-
 2,6-dibromohydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum
1.8
-
 O2 cosubstrate 2-chloro-6-methylhydroquinone, 1,6-cleavage, pH 7.0, 23°C Sphingobium chlorophenolicum
2.2
-
 O2 cosubstrate 2,6-dibromohydroquinone, pH 7.0, 23°C Sphingobium chlorophenolicum
2.41
-
 2-chloro-6-methylhydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum
3.05
-
 2,6-dichlorohydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum
4.8
-
 O2 cosubstrate 2,6-dichlorohydroquinone, pH 7.0, 23°C Sphingobium chlorophenolicum

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.7
-
 O2 cosubstrate 2-chloro-6-methylhydroquinone, 1,6-cleavage, pH 7.0, 23°C Sphingobium chlorophenolicum
7
-
 O2 cosubstrate 2-chloro-6-methylhydroquinone, 1,2-cleavage, pH 7.0, 23°C Sphingobium chlorophenolicum
19
-
 O2 cosubstrate 2,6-dibromohydroquinone, pH 7.0, 23°C Sphingobium chlorophenolicum
20
-
 O2 cosubstrate 2,6-dimethylhydroquinone, pH 7.0, 23°C Sphingobium chlorophenolicum
23
-
 2,6-dimethylhydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum
26
-
 O2 cosubstrate 2,6-dichlorohydroquinone, pH 7.0, 23°C Sphingobium chlorophenolicum
540
-
 2-chloro-6-methylhydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum
1000
-
 2,6-dichlorohydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum
1200
-
 2,6-dibromohydroquinone pH 7.0, 23°C Sphingobium chlorophenolicum