Reaction: (1) pentachlorophenol + NADPH + H+ + O2 = 2,3,5,6-tetrachloro-1,4-benzoquinone + NADP+ + chloride + H2O
(2) 2,3,5,6-tetrachlorophenol + NADPH + H+ + O2 = 2,3,5,6-tetrachlorohydroquinone + NADP+ + H2O
Other name(s): pcpB (gene name); pentachlorophenol dechlorinase; pentachlorophenol dehalogenase; pentachlorophenol 4-monooxygenase; PCP hydroxylase; pentachlorophenol hydroxylase; PCB 4-monooxygenase; PCB4MO
Systematic name: pentachlorophenol,NADPH:oxygen oxidoreductase (hydroxylating, dechlorinating)
Comments: 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.
Links to other databases: BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 136111-57-4
References:
1. Schenk, T., Müller, R., Mörsberger, F., Otto, M.K. and Lingens, F. Enzymatic dehalogenation of pentachlorophenol by extracts from Arthrobacter sp. strain ATCC 33790. J. Bacteriol. 171 (1989) 5487-5491. [PMID: 2793827]
2. Xun, L., Topp, E. and Orser, C.S. Diverse substrate range of a Flavobacterium pentachlorophenol hydroxylase and reaction stoichiometries. J. Bacteriol. 174 (1992) 2898-2902. [PMID: 1569020]
3. Xun, L., Topp, E. and Orser, C.S. Confirmation of oxidative dehalogenation of pentachlorophenol by a Flavobacterium pentachlorophenol hydroxylase. J. Bacteriol. 174 (1992) 5745-5747. [PMID: 1512208]
4. Lange, C.C., Schneider, B.J. and Orser, C.S. Verification of the role of PCP 4-monooxygenase in chlorine elimination from pentachlorophenol by Flavobacterium sp. strain ATCC 39723. Biochem. Biophys. Res. Commun. 219 (1996) 146-149. [PMID: 8619798]
5. Nakamura, T., Motoyama, T., Hirono, S. and Yamaguchi, I. Identification, characterization, and site-directed mutagenesis of recombinant pentachlorophenol 4-monooxygenase. Biochim. Biophys. Acta 1700 (2004) 151-159. [PMID: 15262224]
6. Chen, L. and Yang, J. Biochemical characterization of the tetrachlorobenzoquinone reductase involved in the biodegradation of pentachlorophenol. Int J Mol Sci 9 (2008) 198-212. [PMID: 19325743]
7. Hlouchova, K., Rudolph, J., Pietari, J.M., Behlen, L.S. and Copley, S.D. Pentachlorophenol hydroxylase, a poorly functioning enzyme required for degradation of pentachlorophenol by Sphingobium chlorophenolicum. Biochemistry 51 (2012) 3848-3860. [PMID: 22482720]
8. Rudolph, J., Erbse, A.H., Behlen, L.S. and Copley, S.D. A radical intermediate in the conversion of pentachlorophenol to tetrachlorohydroquinone by Sphingobium chlorophenolicum. Biochemistry 53 (2014) 6539-6549. [PMID: 25238136]