Entry
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)
Substrate
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
ec00361 Chlorocyclohexane and chlorobenzene degradation
ec01120 Microbial metabolism in diverse environments
Orthology
K03391 pentachlorophenol monooxygenase
Genes
Taxonomy
Reference
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
Reference
Authors
Xun L, Topp E, Orser CS.
Title
Diverse substrate range of a Flavobacterium pentachlorophenol hydroxylase and reaction stoichiometries.
Journal
Reference
Authors
Xun L, Topp E, Orser CS.
Title
Confirmation of oxidative dehalogenation of pentachlorophenol by a Flavobacterium pentachlorophenol hydroxylase.
Journal
Reference
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
Reference
Authors
Nakamura T, Motoyama T, Hirono S, Yamaguchi I.
Title
Identification, characterization, and site-directed mutagenesis of recombinant pentachlorophenol 4-monooxygenase.
Journal
Reference
Authors
Chen L, Yang J
Title
Biochemical characterization of the tetrachlorobenzoquinone reductase involved in the biodegradation of pentachlorophenol.
Journal
Reference
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
Reference
Authors
Rudolph J, Erbse AH, Behlen LS, Copley SD
Title
A radical intermediate in the conversion of pentachlorophenol to tetrachlorohydroquinone by Sphingobium chlorophenolicum.
Journal
Other DBs
UM-BBD (Biocatalysis/Biodegradation Database): 1.14.13.50