KEGG   ENZYME: 1.14.14.172
Entry
EC 1.14.14.172              Enzyme                                 
Name
3,5,6-trichloropyridin-2-ol 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
3,5,6-trichloropyridin-2-ol,FADH2:oxygen oxidoreductase (dechlorinating)
Reaction(IUBMB)
(1) 3,5,6-trichloropyridin-2-ol + FADH2 + O2 = 3,6-dichloropyridine-2,5-dione + Cl- + FAD + H2O [RN:R12617];
(2) 3,6-dichloropyridine-2,5-diol + FADH2 + O2 = 6-chloro-3-hydroxypyridine-2,5-dione + Cl- + FAD + H2O [RN:R12618];
(3) 6-chloropyridine-2,3,5-triol + FADH2 + O2 = 3,6-dihydroxypyridine-2,5-dione + Cl- + FAD + H2O [RN:R12619]
Reaction(KEGG)
R12617 R12618 R12619
Substrate
3,5,6-trichloropyridin-2-ol [CPD:C22282];
FADH2 [CPD:C01352];
O2 [CPD:C00007];
3,6-dichloropyridine-2,5-diol [CPD:C22285];
6-chloropyridine-2,3,5-triol [CPD:C22286]
Product
3,6-dichloropyridine-2,5-dione [CPD:C22283];
Cl- [CPD:C00698];
FAD [CPD:C00016];
H2O [CPD:C00001];
6-chloro-3-hydroxypyridine-2,5-dione [CPD:C22284];
3,6-dihydroxypyridine-2,5-dione [CPD:C22287]
Comment
The enzyme, characterized from a number of bacterial species, participates in the degradation of 3,5,6-trichloropyridin-2-ol (TCP), a metabolite of the common organophosphorus insecticide chlorpyrifos. The enzyme is a multifunctional flavin-dependent monooxygenase that displaces three chlorine atoms by attacking three 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 next step. The large amount of FADH2 that is required is generated by a dedicated flavin reductase (TcpX). cf. EC 1.14.14.173, 2,4,6-trichlorophenol monooxygenase.
History
EC 1.14.14.172 created 2020
Orthology
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)
CNAN: A2G96_12450
PHS: C2L64_40520
PTER: C2L65_19195
PPAI: E1956_22235
SRC: M271_03085
SCAD: DN051_03580
SDX: C4B68_04165
SFY: GFH48_02550
SCHF: IPT68_01680
SSPN: LXH13_00190
SCYN: N8I84_40615
AGLA: OIE69_10100 OIE69_40295
PDX: Psed_2279
 » show all
Reference
1  [PMID:24056464]
  Authors
Li J, Huang Y, Hou Y, Li X, Cao H, Cui Z
  Title
Novel gene clusters and metabolic pathway involved in 3,5,6-trichloro-2-pyridinol degradation by Ralstonia sp. strain T6.
  Journal
Appl Environ Microbiol 79:7445-53 (2013)
DOI:10.1128/AEM.01817-13
  Sequence
[ag:AGC65458 AGC65457]
Reference
2  [PMID:30721044]
  Authors
Fang L, Shi T, Chen Y, Wu X, Zhang C, Tang X, Li QX, Hua R
  Title
Kinetics and Catabolic Pathways of the Insecticide Chlorpyrifos, Annotation of the Degradation Genes, and Characterization of Enzymes TcpA and Fre in Cupriavidus nantongensis X1(T).
  Journal
J Agric Food Chem 67:2245-2254 (2019)
DOI:10.1021/acs.jafc.9b00173
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.172
IUBMB Enzyme Nomenclature: 1.14.14.172
ExPASy - ENZYME nomenclature database: 1.14.14.172
BRENDA, the Enzyme Database: 1.14.14.172

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Chemical substance (11)   
   KEGG COMPOUND (11)   
Chemical reaction (3)   
   KEGG REACTION (3)   
Gene (20)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (19)   
All databases (34)   

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