KEGG   ENZYME: 1.14.19.57Help
Entry
EC 1.14.19.57               Enzyme                                 

Name
1H-pyrrole-2-carbonyl-[peptidyl-carrier protein] brominase;
bmp2 (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
1H-pyrrole-2-carbonyl-[peptidyl-carrier protein]:FADH2 oxidoreductase (brominating)
Reaction(IUBMB)
1H-pyrrole-2-carbonyl-[Bmp1 peptidyl-carrier protein] + 3 FADH2 + 3 bromide + 3 O2 = 3,4,5-tribromo-1H-pyrrole-2-carbonyl-[Bmp1 peptidyl-carrier protein] + 3 FAD + 6 H2O (overall reaction) [RN:R12030];
(1a) 1H-pyrrole-2-carbonyl-[Bmp1 peptidyl-carrier protein] + FADH2 + bromide + O2 = 5-bromo-1H-pyrrole-2-carbonyl-[Bmp1 peptidyl-carrier protein] + FAD + 2 H2O [RN:R12027];
(1b) 5-bromo-1H-pyrrole-2-carbonyl-[Bmp1 peptidyl-carrier protein] + FADH2 + bromide + O2 = 4,5-dibromo-1H-pyrrole-2-carbonyl-[Bmp1 peptidyl-carrier protein] + FAD + 2 H2O [RN:R12028];
(1c) 4,5-dibromo-1H-pyrrole-2-carbonyl-[Bmp1 peptidyl-carrier protein] + FADH2 + bromide + O2 = 3,4,5-tribromo-1H-pyrrole-2-carbonyl-[Bmp1 peptidyl-carrier protein] + FAD + 2 H2O [RN:R12029]
Reaction(KEGG)
Substrate
1H-pyrrole-2-carbonyl-[Bmp1 peptidyl-carrier protein];
FADH2 [CPD:C01352];
bromide [CPD:C01324];
O2 [CPD:C00007];
5-bromo-1H-pyrrole-2-carbonyl-[Bmp1 peptidyl-carrier protein];
4,5-dibromo-1H-pyrrole-2-carbonyl-[Bmp1 peptidyl-carrier protein]
Product
3,4,5-tribromo-1H-pyrrole-2-carbonyl-[Bmp1 peptidyl-carrier protein];
FAD [CPD:C00016];
H2O [CPD:C00001];
5-bromo-1H-pyrrole-2-carbonyl-[Bmp1 peptidyl-carrier protein];
4,5-dibromo-1H-pyrrole-2-carbonyl-[Bmp1 peptidyl-carrier protein]
Comment
The enzyme, characterized from marine bacteria of the Pseudoalteromonas genus, belongs to a family of FAD-dependent halogenases that act on acyl-carrier protein-tethered substrates. It catalyses three successive rounds of bromination. While the order has not been verified, it is believed to resemble that of EC 1.14.19.56, S-(1H-pyrrole-2-carbonyl)-[peptidyl-carrier protein] chlorinase, due to significant sequence homology. Reduced FAD is provided in situ by a dedicated reductase and diffuses into the active site, where it reacts with the oxygen and bromide ion, resulting in formation of a bromoamine intermediate on a catalytic lysine side chain, and the eventual transfer of the bromide to the substrate. The enzyme from Pseudoalteromonas luteoviolacea 2ta16 is specific for bromide and does not accept chloride.
History
EC 1.14.19.57 created 2018
Orthology
K22692  1H-pyrrole-2-carbonyl-[peptidyl-carrier protein] brominase
Genes
PPHE: PP2015_463
PLZ: S4054249_08570
MME: Marme_4089
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_463]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.19.57
IUBMB Enzyme Nomenclature: 1.14.19.57
ExPASy - ENZYME nomenclature database: 1.14.19.57
BRENDA, the Enzyme Database: 1.14.19.57

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