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Literature summary for 1.11.1.10 extracted from
- Halogenation of estrogens catalysed by a fungal chloroperoxidase (2021), Nat. Prod. Res., FEHLT, 0000 .
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| additional information | - |
additional information | Michaelis-Menten kinetics | Leptoxyphium fumago | |
| 0.0033 | - |
estrone | with Br-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago |  |
| 0.0048 | - |
beta-estradiol | with Br-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
| 0.0066 | - |
estrone | with Cl-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
| 0.0066 | - |
beta-estradiol | with Cl-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
| 0.152 | - |
equiline | with Br-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
| 0.216 | - |
equiline | with Cl-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago |
Metals/Ions
| Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|
| Fe2+ | required | Leptoxyphium fumago | |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| beta-estradiol + bromide + H2O2 | Leptoxyphium fumago | - |
? + 2 H2O | - |
? | |
| beta-estradiol + chloride + H2O2 | Leptoxyphium fumago | - |
? + 2 H2O | - |
? | |
| carvacrol + chloride + H2O2 | Leptoxyphium fumago | - |
? + 2 H2O | - |
? | |
| equiline + bromide + H2O2 | Leptoxyphium fumago | - |
? + 2 H2O | - |
? | |
| equiline + chloride + H2O2 | Leptoxyphium fumago | - |
? + 2 H2O | - |
? | |
| estrone + bromide + H2O2 | Leptoxyphium fumago | - |
? + 2 H2O | - |
? | |
| estrone + chloride + H2O2 | Leptoxyphium fumago | - |
? + 2 H2O | - |
? | |
| hesperetin + chloride + H2O2 | Leptoxyphium fumago | - |
? + 2 H2O | - |
? | |
| naringenin + chloride + H2O2 | Leptoxyphium fumago | - |
? + 2 H2O | - |
? | |
| pyrene + chloride + H2O2 | Leptoxyphium fumago | - |
? + 2 H2O | - |
? | |
| RH + chloride + H2O2 | Leptoxyphium fumago | - |
RCl + 2 H2O | - |
? | |
| thymol + chloride + H2O2 | Leptoxyphium fumago | - |
? + 2 H2O | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Leptoxyphium fumago | P04963 | Caldariomyces fumago | - |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| beta-estradiol + bromide + H2O2 | - |
Leptoxyphium fumago | ? + 2 H2O | - |
? | |
| beta-estradiol + chloride + H2O2 | - |
Leptoxyphium fumago | ? + 2 H2O | - |
? | |
| carvacrol + chloride + H2O2 | - |
Leptoxyphium fumago | ? + 2 H2O | - |
? | |
| equiline + bromide + H2O2 | - |
Leptoxyphium fumago | ? + 2 H2O | - |
? | |
| equiline + chloride + H2O2 | - |
Leptoxyphium fumago | ? + 2 H2O | - |
? | |
| estradiol + 2 bromide + 2 H2O2 | - |
Leptoxyphium fumago | 2,4-bromo beta-estradiol + 4 H2O | - |
? | |
| estradiol + 2 chloride + 2 H2O2 | - |
Leptoxyphium fumago | 2,4-dichloro beta-estradiol + 4 H2O | - |
? | |
| estradiol + bromide + H2O2 | - |
Leptoxyphium fumago | 2-bromo beta-estradiol + 2 H2O | - |
? | |
| estradiol + bromide + H2O2 | - |
Leptoxyphium fumago | 4-bromo beta-estradiol + 2 H2O | - |
? | |
| estradiol + chloride + H2O2 | - |
Leptoxyphium fumago | 2-chloro beta-estradiol + 2 H2O | - |
? | |
| estradiol + chloride + H2O2 | - |
Leptoxyphium fumago | 4-chloro beta-estradiol + 2 H2O | - |
? | |
| estrone + bromide + H2O2 | - |
Leptoxyphium fumago | ? + 2 H2O | - |
? | |
| estrone + chloride + H2O2 | - |
Leptoxyphium fumago | ? + 2 H2O | - |
? | |
| hesperetin + chloride + H2O2 | - |
Leptoxyphium fumago | ? + 2 H2O | - |
? | |
| additional information | CPO is a haeme-thiolate peroxidase requiring the presence of H2O2 to form an activated enzymatic species, responsible for oxidising either halides or organic substrates. CPO catalyses the halogenation of estrogens at comparable rates to other aromatic compounds | Leptoxyphium fumago | ? | - |
- |
|
| naringenin + chloride + H2O2 | - |
Leptoxyphium fumago | ? + 2 H2O | - |
? | |
| pyrene + chloride + H2O2 | - |
Leptoxyphium fumago | ? + 2 H2O | - |
? | |
| RH + chloride + H2O2 | - |
Leptoxyphium fumago | RCl + 2 H2O | - |
? | |
| thymol + chloride + H2O2 | - |
Leptoxyphium fumago | ? + 2 H2O | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| chloroperoxidase | - |
Leptoxyphium fumago |
| CPO | - |
Leptoxyphium fumago |
| haeme-thiolate peroxidase | - |
Leptoxyphium fumago |
| More | see also EC 1.11.1.18 | Leptoxyphium fumago |
Turnover Number [1/s]
| Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 33 | - |
beta-estradiol | with Cl-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
| 120 | - |
estrone | with Cl-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
| 330 | - |
estrone | with Br-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
| 420 | - |
beta-estradiol | with Br-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
| 1930 | - |
equiline | with Cl-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
| 1970 | - |
equiline | with Br-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago |
Cofactor
| Cofactor | Comment | Organism | Structure |
|---|---|---|---|
| heme | - |
Leptoxyphium fumago | |
General Information
| General Information | Comment | Organism |
|---|---|---|
| physiological function | chloroperoxidase (CPO) is a heme-thiolate enzyme able to catalyse the halogenation and oxidation of a wide range of organic substrates. CPO-catalysed chlorination and bromination reaction of natural estrogens, beta-estradiol, estrone and equiline are efficiently converted to halogenated compounds in the presence of chloride or bromide and hydrogen peroxide. The bromination reaction proceeds more efficiently than the chlorination reaction. Three major products are detected for chlorination of beta-estradiol, two of them are monohalogenated compounds while a third product is a dihalogenated compound at positions 2 and 4 of the aromatic ring A. Chlorinated compounds are not substrates for tyrosinase, suggesting that the halogenated form of estrogens is less susceptible to form o-quinones. Chlorinated estradiol is not a substrate of tyrosinase. Whereas E2 is completely consumed in the presence of tyrosinase, E2-derived chlorinated compounds are not transformed. 2,4-Dichloroestradiol is 90fold less estrogenic compared to beta-estradiol | Leptoxyphium fumago |
kcat/KM [mM/s]
| kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 5000 | - |
beta-estradiol | with Cl-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
| 8935 | - |
equiline | with Cl-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
| 12960 | - |
equiline | with Br-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
| 18181 | - |
estrone | with Cl-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
| 87500 | - |
beta-estradiol | with Br-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
| 100000 | - |
estrone | with Br-, pH 3.0, temperature not specified in the publication | Leptoxyphium fumago | |
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