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Literature summary extracted from
- Formation of environmentally relevant polyhalogenated carbazoles from chloroperoxidase-catalyzed halogenation of carbazole (2018), Environ. Pollut., 232, 264-273 .
Localization
| EC Number | Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|---|
| 1.11.1.10 | extracellular | the enzyme is secreted | Leptoxyphium fumago | - |
- |
| 1.11.1.18 | extracellular | the enzyme is secreted | Leptoxyphium fumago | - |
- |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.11.1.10 | 2-chlorodimedone + chloride + H2O2 | Leptoxyphium fumago | model substrate monochlorodimedone | 1,1-dimethyl-4,4-dichloro-3,5-cyclohexanedione + 2 H2O | - |
? |  |
| 1.11.1.10 | additional information | Leptoxyphium fumago | production of polyhalogenated carbazoles (PHCs) from halogenation of carbazole in the presence of bromide and/or chloride under the catalysis of chloroperoxidase (CPO) isolated from the marine fungus Caldariomyces fumago, see also EC 1.11.1.18. A total of 25 congeners including mono-to tetra-substituted chlorinated, brominated, and mixed halogenated carbazoles (with substitution patterns of -BrCl, -BrCl2, -BrCl3, -Br2Cl, -Br2Cl2, and -Br3Cl) are produced from the reactions under various conditions. The PHC product profiles are apparently dependent on the halide concentrations. In the CPO-mediated chlorination of carbazole, 3-mono- and 3,6-dichlorocarbazoles predominated in the formation products. In addition to the less abundant mixed halogenated carbazoles (-Br2Cl), 1,3,6-tri- and 1,3,6,8-tetrabromocarbazoles are the dominant products in reactions containing both Br- and Cl- | ? | - |
- |
|
| 1.11.1.10 | RH + chloride + H2O2 | Leptoxyphium fumago | - |
RCl + 2 H2O | - |
? | |
| 1.11.1.18 | 2-chlorodimedone + chloride + H2O2 | Leptoxyphium fumago | model substrate monochlorodimedone, activity of EC 1.11.1.10 | 1,1-dimethyl-4,4-dichloro-3,5-cyclohexanedione + 2 H2O | - |
? | |
| 1.11.1.18 | additional information | Leptoxyphium fumago | production of polyhalogenated carbazoles (PHCs) from halogenation of carbazole in the presence of bromide and/or chloride under the catalysis of chloroperoxidase (CPO) isolated from the marine fungus Caldariomyces fumago, see also EC 1.11.1.10. A total of 25 congeners including mono-to tetra-substituted chlorinated, brominated, and mixed halogenated carbazoles (with substitution patterns of -BrCl, -BrCl2, -BrCl3, -Br2Cl, -Br2Cl2, and -Br3Cl) are produced from the reactions under various conditions. The PHC product profiles are apparently dependent on the halide concentrations. In the CPO-mediated chlorination of carbazole, 3-mono- and 3,6-dichlorocarbazoles predominated in the formation products. In addition to the less abundant mixed halogenated carbazoles (-Br2Cl), 1,3,6-tri- and 1,3,6,8-tetrabromocarbazoles are the dominant products in reactions containing both Br- and Cl- | ? | - |
- |
|
| 1.11.1.18 | RH + bromide + H2O2 | Leptoxyphium fumago | - |
RBr + 2 H2O | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.11.1.10 | Leptoxyphium fumago | P04963 | Caldariomyces fumago | - |
| 1.11.1.18 | Leptoxyphium fumago | P04963 | Caldariomyces fumago | - |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.11.1.10 | 2-chlorodimedone + chloride + H2O2 | model substrate monochlorodimedone | Leptoxyphium fumago | 1,1-dimethyl-4,4-dichloro-3,5-cyclohexanedione + 2 H2O | - |
? | |
| 1.11.1.10 | additional information | production of polyhalogenated carbazoles (PHCs) from halogenation of carbazole in the presence of bromide and/or chloride under the catalysis of chloroperoxidase (CPO) isolated from the marine fungus Caldariomyces fumago, see also EC 1.11.1.18. A total of 25 congeners including mono-to tetra-substituted chlorinated, brominated, and mixed halogenated carbazoles (with substitution patterns of -BrCl, -BrCl2, -BrCl3, -Br2Cl, -Br2Cl2, and -Br3Cl) are produced from the reactions under various conditions. The PHC product profiles are apparently dependent on the halide concentrations. In the CPO-mediated chlorination of carbazole, 3-mono- and 3,6-dichlorocarbazoles predominated in the formation products. In addition to the less abundant mixed halogenated carbazoles (-Br2Cl), 1,3,6-tri- and 1,3,6,8-tetrabromocarbazoles are the dominant products in reactions containing both Br- and Cl- | Leptoxyphium fumago | ? | - |
- |
|
| 1.11.1.10 | RH + chloride + H2O2 | - |
Leptoxyphium fumago | RCl + 2 H2O | - |
? | |
| 1.11.1.18 | 2-chlorodimedone + chloride + H2O2 | model substrate monochlorodimedone, activity of EC 1.11.1.10 | Leptoxyphium fumago | 1,1-dimethyl-4,4-dichloro-3,5-cyclohexanedione + 2 H2O | - |
? | |
| 1.11.1.18 | additional information | production of polyhalogenated carbazoles (PHCs) from halogenation of carbazole in the presence of bromide and/or chloride under the catalysis of chloroperoxidase (CPO) isolated from the marine fungus Caldariomyces fumago, see also EC 1.11.1.10. A total of 25 congeners including mono-to tetra-substituted chlorinated, brominated, and mixed halogenated carbazoles (with substitution patterns of -BrCl, -BrCl2, -BrCl3, -Br2Cl, -Br2Cl2, and -Br3Cl) are produced from the reactions under various conditions. The PHC product profiles are apparently dependent on the halide concentrations. In the CPO-mediated chlorination of carbazole, 3-mono- and 3,6-dichlorocarbazoles predominated in the formation products. In addition to the less abundant mixed halogenated carbazoles (-Br2Cl), 1,3,6-tri- and 1,3,6,8-tetrabromocarbazoles are the dominant products in reactions containing both Br- and Cl- | Leptoxyphium fumago | ? | - |
- |
|
| 1.11.1.18 | RH + bromide + H2O2 | - |
Leptoxyphium fumago | RBr + 2 H2O | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.11.1.10 | chloroperoxidase | - |
Leptoxyphium fumago |
| 1.11.1.10 | CPO | - |
Leptoxyphium fumago |
| 1.11.1.10 | More | see also EC 1.11.1.18 | Leptoxyphium fumago |
| 1.11.1.18 | More | see also EC 1.11.1.10 | Leptoxyphium fumago |
Temperature Optimum [°C]
| EC Number | Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|---|
| 1.11.1.10 | 25 | - |
assay at | Leptoxyphium fumago |
| 1.11.1.18 | 25 | - |
assay at | Leptoxyphium fumago |
pH Optimum
| EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|---|
| 1.11.1.10 | 3 | - |
assay at | Leptoxyphium fumago |
| 1.11.1.18 | 3 | - |
assay at | Leptoxyphium fumago |
pH Range
| EC Number | pH Minimum | pH Maximum | Comment | Organism |
|---|---|---|---|---|
| 1.11.1.10 | 3 | 7 | activity range for CPO-catalyzed halogenation of carbazole, preferential formation of higher substituted bromocarbazoles under acidic conditions | Leptoxyphium fumago |
| 1.11.1.18 | 3 | 7 | activity range for CPO-catalyzed halogenation of carbazole, preferential formation of higher substituted bromocarbazoles under acidic conditions | Leptoxyphium fumago |
Cofactor
| EC Number | Cofactor | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.11.1.10 | heme | - |
Leptoxyphium fumago | |
| 1.11.1.18 | heme | - |
Leptoxyphium fumago | |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 1.11.1.10 | physiological function | chloroperoxidase (CPO), secreted by the marine fungus Caldariomyces fumago, is a versatile enzyme with the capacity to catalyze the incorporation of halogen atoms into organic molecules in the presence of peroxides such as H2O2. Production of polyhalogenated carbazoles (PHCs) from halogenation of carbazole in the presence of bromide and/or chloride under the catalysis of chloroperoxidase (CPO) isolated from the marine fungus Caldariomyces fumago. CPO-catalyzed halogenation of carbazole may play an important role in the natural formation of PHCs. PHCs exhibit dioxin-like toxicity and are persistent and bioaccumulative. PHCs induce cytochrome P450 enzymes and certain other enzyme activities. The chlorinated and brominated carbazoles produced in the reactions with Cl- and Br- in vitro are also found in aquatic environments, overview | Leptoxyphium fumago |
| 1.11.1.18 | physiological function | chloroperoxidase (CPO), secreted by the marine fungus Caldariomyces fumago, is a versatile enzyme with the capacity to catalyze the incorporation of halogen atoms into organic molecules in the presence of peroxides such as H2O2. Production of polyhalogenated carbazoles (PHCs) from halogenation of carbazole in the presence of bromide and/or chloride under the catalysis of chloroperoxidase (CPO) isolated from the marine fungus Caldariomyces fumago. CPO-catalyzed halogenation of carbazole may play an important role in the natural formation of PHCs. PHCs exhibit dioxin-like toxicity and are persistent and bioaccumulative. PHCs induce cytochrome P450 enzymes and certain other enzyme activities. The chlorinated and brominated carbazoles produced in the reactions with Cl- and Br- in vitro are also found in aquatic environments, overview | Leptoxyphium fumago |
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