Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water

4-hydroxybenzoate:NADPH oxidoreductase (brominating, decarboxylating)

(1) 4-hydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+ = 2,4-dibromophenol + 2 NADP+ + CO2 + 4 H2O (overall reaction) [RN:R12013];
(1a) 4-hydroxybenzoate + NADPH + bromide + O2 + H+ = 3-bromo-4-hydroxybenzoate + NADP+ + 2 H2O [RN:R12015];
(1b) 3-bromo-4-hydroxybenzoate + NADPH + bromide + O2 + H+ = 2,4-dibromophenol + NADP+ + CO2 + 2 H2O [RN:R12016];
(2) 3,4-dihydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+ = 3,5-dibromobenzene-1,2-diol + 2 NADP+ + CO2 + 4 H2O (overall reaction) [RN:R12018];
(2a) 3,4-dihydroxybenzoate + NADPH + bromide + O2 + H+ = 3-bromo-4,5-dihydroxybenzoate + NADP+ + 2 H2O [RN:R12019];
(2b) 3-bromo-4,5-dihydroxybenzoate + NADPH + bromide + O2 + H+ = 3,5-dibromobenzene-1,2-diol + NADP+ + CO2 + 2 H2O [RN:R12020]

R12013 R12015 R12016 R12018 R12019 R12020

4-hydroxybenzoate [CPD:C00156];
NADPH [CPD:C00005];
bromide [CPD:C01324];
O2 [CPD:C00007];
H+ [CPD:C00080];
3-bromo-4-hydroxybenzoate [CPD:C21850];
3,4-dihydroxybenzoate [CPD:C00230];
3-bromo-4,5-dihydroxybenzoate [CPD:C21853]

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.

EC 1.14.19.55 created 2018

1  [PMID:24974229]

Agarwal V, El Gamal AA, Yamanaka K, Poth D, Kersten RD, Schorn M, Allen EE, Moore BS

Biosynthesis of polybrominated aromatic organic compounds by marine bacteria.

Nat Chem Biol 10:640-7 (2014)
DOI:10.1038/nchembio.1564

[pphe:PP2015_466]

2  [PMID:25061970]

Agarwal V, Moore BS

Enzymatic synthesis of polybrominated dioxins from the marine environment.

ACS Chem Biol 9:1980-4 (2014)
DOI:10.1021/cb5004338