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Information on EC 1.14.19.55 - 4-hydroxybenzoate brominase (decarboxylating) for references in articles please use BRENDA:EC1.14.19.55
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IUBMB Comments Contains FAD. The enzyme, described from epiphytic marine bacteria of the genera Pseudoalteromonas and Marinomonas, is an unusual single-component FAD-dependent halogenase that contains a distinct NAD(P)H binding domain and does not require an additional flavin reductase for activity. The enzyme catalyses a bromination of its substrate, followed by a second bromination concurrent with decarboxylation.
The enzyme appears in viruses and cellular organisms
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bmp5
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gene name
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3,4-dihydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+ = 3,5-dibromobenzene-1,2-diol + 2 NADP+ + CO2 + 4 H2O
(2)
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3,4-dihydroxybenzoate + NADPH + bromide + O2 + H+ = 3-bromo-4,5-dihydroxybenzoate + NADP+ + 2 H2O
(2a)
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3-bromo-4,5-dihydroxybenzoate + NADPH + bromide + O2 + H+ = 3,5-dibromobenzene-1,2-diol + NADP+ + CO2 + 2 H2O
(2b)
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3-bromo-4-hydroxybenzoate + NADPH + bromide + O2 + H+ = 2,4-dibromophenol + NADP+ + CO2 + 2 H2O
(1b)
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4-hydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+ = 2,4-dibromophenol + 2 NADP+ + CO2 + 4 H2O
(1)
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4-hydroxybenzoate + NADPH + bromide + O2 + H+ = 3-bromo-4-hydroxybenzoate + NADP+ + 2 H2O
(1a)
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4-hydroxybenzoate:NADPH oxidoreductase (brominating, decarboxylating)
Contains FAD. The enzyme, described from epiphytic marine bacteria of the genera Pseudoalteromonas and Marinomonas, is an unusual single-component FAD-dependent halogenase that contains a distinct NAD(P)H binding domain and does not require an additional flavin reductase for activity. The enzyme catalyses a bromination of its substrate, followed by a second bromination concurrent with decarboxylation.
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2,4-dihydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+
2,4-dibromo-6-hydroxyphenol + 4-bromo-2-hydroxyphenol + 2 NADP+ + CO2 + 4 H2O
3,4-dihydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+
2,4-dibromo-6-hydroxyphenol + 4-bromo-2-hydroxyphenol + 2 NADP+ + CO2 + 4 H2O
3-bromo-4-hydroxybenzoate + NADPH + bromide + O2 + H+
2,4-dibromophenol + NADP+ + CO2 + 2 H2O
4-hydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+
2,4-dibromophenol + 2 NADP+ + CO2 + 4 H2O
4-hydroxybenzoate + 2 NADPH + 2 iodide + 2 O2 + 2 H+
2,4-diiodophenol + 2 NADP+ + CO2 + 4 H2O
4-hydroxybenzoate + NADPH + bromide + O2 + H+
3-bromo-4-hydroxybenzoate + NADP+ + 2 H2O
additional information
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2,4-dihydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+
2,4-dibromo-6-hydroxyphenol + 4-bromo-2-hydroxyphenol + 2 NADP+ + CO2 + 4 H2O
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2,4-dihydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+
2,4-dibromo-6-hydroxyphenol + 4-bromo-2-hydroxyphenol + 2 NADP+ + CO2 + 4 H2O
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3,4-dihydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+
2,4-dibromo-6-hydroxyphenol + 4-bromo-2-hydroxyphenol + 2 NADP+ + CO2 + 4 H2O
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3,4-dihydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+
2,4-dibromo-6-hydroxyphenol + 4-bromo-2-hydroxyphenol + 2 NADP+ + CO2 + 4 H2O
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3-bromo-4-hydroxybenzoate + NADPH + bromide + O2 + H+
2,4-dibromophenol + NADP+ + CO2 + 2 H2O
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3-bromo-4-hydroxybenzoate + NADPH + bromide + O2 + H+
2,4-dibromophenol + NADP+ + CO2 + 2 H2O
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4-hydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+
2,4-dibromophenol + 2 NADP+ + CO2 + 4 H2O
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4-hydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+
2,4-dibromophenol + 2 NADP+ + CO2 + 4 H2O
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4-hydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+
2,4-dibromophenol + 2 NADP+ + CO2 + 4 H2O
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4-hydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+
2,4-dibromophenol + 2 NADP+ + CO2 + 4 H2O
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4-hydroxybenzoate + 2 NADPH + 2 iodide + 2 O2 + 2 H+
2,4-diiodophenol + 2 NADP+ + CO2 + 4 H2O
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4-hydroxybenzoate + 2 NADPH + 2 iodide + 2 O2 + 2 H+
2,4-diiodophenol + 2 NADP+ + CO2 + 4 H2O
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4-hydroxybenzoate + NADPH + bromide + O2 + H+
3-bromo-4-hydroxybenzoate + NADP+ + 2 H2O
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4-hydroxybenzoate + NADPH + bromide + O2 + H+
3-bromo-4-hydroxybenzoate + NADP+ + 2 H2O
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additional information
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no substrate: chloride
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additional information
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no substrate: chloride
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FAD
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Bmp5 does not require the addition of a flavin reductase to regenerate FADH2 in situ
NADPH
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absolutely required
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brenda
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physiological function
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coexpression of Bmp5 with flavin-dependent 4-hydroxybenzoate-3-hydroxylase m3553 in Escherichia coli yields 2,4-dibromophenol, 4-bromo-2-hydroxyphenol and 2,4-dibromo-6-hydroxyphenol. Coexpression of Bmp5, Cyp450 enzyme Bmp7, and m3553, and supplementation of the culture medium with exogenous 4-hydroxybenzoic acid, leads to production of bromophenols, bromocatechols, mono- and dihydroxylated dibenzo-p-dioxins, mono- and dihydroxy-brominated diphenyl ethers, as well as biphenyls
physiological function
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deletion of the Bmp5 gene eliminates the synthesis of bromophenol-containing species
physiological function
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coexpression of Bmp5 with flavin-dependent 4-hydroxybenzoate-3-hydroxylase m3553 in Escherichia coli yields 2,4-dibromophenol, 4-bromo-2-hydroxyphenol and 2,4-dibromo-6-hydroxyphenol. Coexpression of Bmp5, Cyp450 enzyme Bmp7, and m3553, and supplementation of the culture medium with exogenous 4-hydroxybenzoic acid, leads to production of bromophenols, bromocatechols, mono- and dihydroxylated dibenzo-p-dioxins, mono- and dihydroxy-brominated diphenyl ethers, as well as biphenyls
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physiological function
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deletion of the Bmp5 gene eliminates the synthesis of bromophenol-containing species
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expression in Escherichia coli
expression in Escherichia coli
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expression in Escherichia coli
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Agarwal, V.; Moore, B.
Enzymatic synthesis of polybrominated dioxins from the marine environment
ACS Chem. Biol.
9
1980-1984
2014
Marinomonas mediterranea, Marinomonas mediterranea MMB-1
brenda
Agarwal, V.; El Gamal, A.; Yamanaka, K.; Poth, D.; Kersten, R.; Schorn, M.; Allen, E.; Moore, B.
Biosynthesis of polybrominated aromatic organic compounds by marine bacteria
Nat. Chem. Biol.
10
640-647
2014
Pseudoalteromonas luteoviolacea, Pseudoalteromonas luteoviolacea 2ta16
brenda
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1.14.19.55 4-hydroxybenzoate brominase (decarboxylating)
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