KEGG   ORTHOLOGY: K03391Help
Entry
K03391                      KO                                     

Name
pcpB
Definition
pentachlorophenol monooxygenase [EC:1.14.13.50]
Pathway
Chlorocyclohexane and chlorobenzene degradation
Fluorobenzoate degradation
Brite
KEGG Orthology (KO) [BR:ko00001]
 Metabolism
  Xenobiotics biodegradation and metabolism
   00364 Fluorobenzoate degradation
    K03391  pcpB; pentachlorophenol monooxygenase
   00361 Chlorocyclohexane and chlorobenzene degradation
    K03391  pcpB; pentachlorophenol monooxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.13  With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.13.50  pentachlorophenol monooxygenase
     K03391  pcpB; pentachlorophenol monooxygenase
BRITE hierarchy
Other DBs
Genes
SCH: 
TaxonomyKoalaUniProt
Reference
  Authors
Yadid I, Rudolph J, Hlouchova K, Copley SD
  Title
Sequestration of a highly reactive intermediate in an evolving pathway for degradation of pentachlorophenol.
  Journal
Proc Natl Acad Sci U S A 110:E2182-90 (2013)
DOI:10.1073/pnas.1214052110
KEGG   ENZYME: 1.14.13.50Help
Entry
EC 1.14.13.50               Enzyme                                 

Name
pentachlorophenol monooxygenase;
pcpB (gene name);
pentachlorophenol dechlorinase;
pentachlorophenol dehalogenase;
pentachlorophenol 4-monooxygenase;
PCP hydroxylase;
pentachlorophenol hydroxylase;
PCB 4-monooxygenase;
PCB4MO
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
pentachlorophenol,NADPH:oxygen oxidoreductase (hydroxylating, dechlorinating)
Reaction(IUBMB)
(1) pentachlorophenol + NADPH + H+ + O2 = 2,3,5,6-tetrachloro-1,4-benzoquinone + NADP+ + chloride + H2O [RN:R03982];
(2) 2,3,5,6-tetrachlorophenol + NADPH + H+ + O2 = 2,3,5,6-tetrachlorohydroquinone + NADP+ + H2O [RN:R07191]
Reaction(KEGG)
R03982 R07191;
(other) R07779
Show
Substrate
pentachlorophenol [CPD:C02575];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007];
2,3,5,6-tetrachlorophenol [CPD:C15505]
Product
2,3,5,6-tetrachloro-1,4-benzoquinone [CPD:C18933];
NADP+ [CPD:C00006];
chloride [CPD:C00698];
H2O [CPD:C00001];
2,3,5,6-tetrachlorohydroquinone [CPD:C03434]
Comment
A flavoprotein (FAD). The enzyme displaces a diverse range of substituents from the 4-position of polyhalogenated phenols but requires that a halogen substituent be present at the 2-position [2]. If C-4 carries a halogen substituent, reaction 1 is catalysed; if C-4 is unsubstituted, reaction 2 is catalysed.
History
EC 1.14.13.50 created 1992, modified 2005, modified 2017
Pathway
Chlorocyclohexane and chlorobenzene degradation
Fluorobenzoate degradation
Metabolic pathways
Microbial metabolism in diverse environments
Orthology
K03391  
pentachlorophenol monooxygenase
Genes
SCH: 
Taxonomy
Reference
1  [PMID:2793827]
  Authors
Schenk T, Muller R, Morsberger F, Otto MK, Lingens F.
  Title
Enzymatic dehalogenation of pentachlorophenol by extracts from Arthrobacter sp. strain ATCC 33790.
  Journal
J. Bacteriol. 171 (1989) 5487-91.
Reference
2  [PMID:1569020]
  Authors
Xun L, Topp E, Orser CS.
  Title
Diverse substrate range of a Flavobacterium pentachlorophenol hydroxylase and reaction stoichiometries.
  Journal
J. Bacteriol. 174 (1992) 2898-902.
Reference
3  [PMID:1512208]
  Authors
Xun L, Topp E, Orser CS.
  Title
Confirmation of oxidative dehalogenation of pentachlorophenol by a Flavobacterium pentachlorophenol hydroxylase.
  Journal
J. Bacteriol. 174 (1992) 5745-7.
Reference
4  [PMID:8619798]
  Authors
Lange CC, Schneider BJ, Orser CS.
  Title
Verification of the role of PCP 4-monooxygenase in chlorine elimination from pentachlorophenol by Flavobacterium sp. strain ATCC 39723.
  Journal
Biochem. Biophys. Res. Commun. 219 (1996) 146-9.
Reference
5  [PMID:15262224]
  Authors
Nakamura T, Motoyama T, Hirono S, Yamaguchi I.
  Title
Identification, characterization, and site-directed mutagenesis of recombinant pentachlorophenol 4-monooxygenase.
  Journal
Biochim. Biophys. Acta. 1700 (2004) 151-9.
Reference
6  [PMID:19325743]
  Authors
Chen L, Yang J
  Title
Biochemical characterization of the tetrachlorobenzoquinone reductase involved in the biodegradation of pentachlorophenol.
  Journal
Int. J. Mol. Sci. 9 (2008) 198-212.
Reference
7  [PMID:22482720]
  Authors
Hlouchova K, Rudolph J, Pietari JM, Behlen LS, Copley SD
  Title
Pentachlorophenol hydroxylase, a poorly functioning enzyme required for degradation of pentachlorophenol by Sphingobium chlorophenolicum.
  Journal
Biochemistry. 51 (2012) 3848-60.
Reference
8  [PMID:25238136]
  Authors
Rudolph J, Erbse AH, Behlen LS, Copley SD
  Title
A radical intermediate in the conversion of pentachlorophenol to tetrachlorohydroquinone by Sphingobium chlorophenolicum.
  Journal
Biochemistry. 53 (2014) 6539-49.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
UM-BBD (Biocatalysis/Biodegradation Database): 
BRENDA, the Enzyme Database: 
CAS: 
136111-57-4
KEGG   REACTION: R07779Help
Entry
R07779                      Reaction                               

Name
bromoxynil,NADPH:oxygen oxidoreductase
Definition
Bromoxynil + 2 NADPH + 2 H+ + Oxygen <=> 2,6-Dibromohydroquinone + 2 NADP+ + Hydrogen cyanide + H2O
Equation
Reaction class
C00005_C00006
C04178_C16248
Enzyme
Pathway
Fluorobenzoate degradation
Microbial metabolism in diverse environments
Orthology
K03391  
pentachlorophenol monooxygenase [EC:1.14.13.50]
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