KEGG   ENZYME: 1.14.19.55Help
Entry
EC 1.14.19.55               Enzyme                                 

Name
4-hydroxybenzoate brominase (decarboxylating);
bmp5 (gene name)
Class
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
BRITE hierarchy
Sysname
4-hydroxybenzoate:NADPH oxidoreductase (brominating, decarboxylating)
Reaction(IUBMB)
(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]
Reaction(KEGG)
Substrate
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]
Product
2,4-dibromophenol [CPD:C14521];
NADP+ [CPD:C00006];
CO2 [CPD:C00011];
H2O [CPD:C00001];
3-bromo-4-hydroxybenzoate [CPD:C21850];
3,5-dibromobenzene-1,2-diol [CPD:C21852];
3-bromo-4,5-dihydroxybenzoate [CPD:C21853]
Comment
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.
History
EC 1.14.19.55 created 2018
Orthology
K05918  4-hydroxybenzoate brominase (decarboxylating)
Genes
PPHE: PP2015_466
MME: Marme_4093
Taxonomy
Reference
1  [PMID:24974229]
  Authors
Agarwal V, El Gamal AA, Yamanaka K, Poth D, Kersten RD, Schorn M, Allen EE, Moore BS
  Title
Biosynthesis of polybrominated aromatic organic compounds by marine bacteria.
  Journal
Nat Chem Biol 10:640-7 (2014)
DOI:10.1038/nchembio.1564
  Sequence
[pphe:PP2015_466]
Reference
2  [PMID:25061970]
  Authors
Agarwal V, Moore BS
  Title
Enzymatic synthesis of polybrominated dioxins from the marine environment.
  Journal
ACS Chem Biol 9:1980-4 (2014)
DOI:10.1021/cb5004338
Other DBs
ExplorEnz - The Enzyme Database: 1.14.19.55
IUBMB Enzyme Nomenclature: 1.14.19.55
ExPASy - ENZYME nomenclature database: 1.14.19.55
BRENDA, the Enzyme Database: 1.14.19.55

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