KEGG   ENZYME: 1.14.14.173
Entry
EC 1.14.14.173              Enzyme                                 

Name
2,4,6-trichlorophenol monooxygenase;
tcpA (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
2,4,6-trichlorophenol,FADH2:oxygen oxidoreductase (dechlorinating)
Reaction(IUBMB)
(1) 2,4,6-trichlorophenol + FADH2 + O2 = 2,6-dichloro-1,4-benzoquinone + Cl- + FAD + H2O [RN:R05449];
(2) 2,6-dichlorohydroquinone + FADH2 + O2 = 2-chloro-6-hydroxy-1,4-benzoquinone + Cl- + FAD + H2O [RN:R12627]
Reaction(KEGG)
R05449 R12627
Substrate
2,4,6-trichlorophenol [CPD:C07098];
FADH2 [CPD:C01352];
O2 [CPD:C00007];
2,6-dichlorohydroquinone [CPD:C07097]
Product
2,6-dichloro-1,4-benzoquinone [CPD:C21103];
Cl- [CPD:C00698];
FAD [CPD:C00016];
H2O [CPD:C00001];
2-chloro-6-hydroxy-1,4-benzoquinone [CPD:C22290]
Comment
The enzyme, characterized from a number of bacterial species, participates in the degradation of 2,4,6-trichlorophenol, a compound that has been used for decades as a wood preservative. The enzyme is a multifunctional flavin-dependent monooxygenase that displaces two chlorine atoms by attacking two different positions in the substrate. Each reaction catalysed by the enzyme displaces a single chlorine and results in formation of a dione, which must be reduced by FADH2 before the monooxygenase could catalyse the second reaction. The large amount of FADH2 that is required is generated by a dedicated flavin reductase (TcpB). cf. EC 1.14.14.172, 3,5,6-trichloropyridin-2-ol monooxygenase.
History
EC 1.14.14.173 created 2020
Pathway
ec00361  Chlorocyclohexane and chlorobenzene degradation
ec01120  Microbial metabolism in diverse environments
Orthology
K15246  chlorophenol-4-monooxygenase
K24293  3,5,6-trichloropyridin-2-ol/2,4,6-trichlorophenol monooxygenase
Genes
RPJ: N234_22415
CNC: CNE_BB1p03440(tcpA)
REU: Reut_A1585
COX: E0W60_29395(tcpA)
PHS: C2L64_40520
PTER: C2L65_19195
SCHF: IPT68_01680
Reference
1  [PMID:12057943]
  Authors
Louie TM, Webster CM, Xun L
  Title
Genetic and biochemical characterization of a 2,4,6-trichlorophenol degradation pathway in Ralstonia eutropha JMP134.
  Journal
J Bacteriol 184:3492-500 (2002)
DOI:10.1128/jb.184.13.3492-3500.2002
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.173
IUBMB Enzyme Nomenclature: 1.14.14.173
ExPASy - ENZYME nomenclature database: 1.14.14.173
BRENDA, the Enzyme Database: 1.14.14.173

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