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Literature summary for 1.11.1.18 extracted from

  • Chen, Y.; Lin, K.; Chen, D.; Wang, K.; Zhou, W.; Wu, Y.; Huang, X.
    Formation of environmentally relevant polyhalogenated carbazoles from chloroperoxidase-catalyzed halogenation of carbazole (2018), Environ. Pollut., 232, 264-273 .
    View publication on PubMed

Localization

Localization Comment Organism GeneOntology No. Textmining
extracellular the enzyme is secreted Leptoxyphium fumago
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Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
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
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?
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- ?
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RH + bromide + H2O2 Leptoxyphium fumago
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RBr + 2 H2O
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?

Organism

Organism UniProt Comment Textmining
Leptoxyphium fumago P04963 Caldariomyces fumago
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
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
-
?
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 ?
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RH + bromide + H2O2
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Leptoxyphium fumago RBr + 2 H2O
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?

Synonyms

Synonyms Comment Organism
More see also EC 1.11.1.10 Leptoxyphium fumago

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
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assay at Leptoxyphium fumago

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
3
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assay at Leptoxyphium fumago

pH Range

pH Minimum pH Maximum Comment Organism
3 7 activity range for CPO-catalyzed halogenation of carbazole, preferential formation of higher substituted bromocarbazoles under acidic conditions Leptoxyphium fumago

Cofactor

Cofactor Comment Organism Structure
heme
-
Leptoxyphium fumago

General Information

General Information Comment Organism
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