Table 1.

EPA priority pollutants (and a few other recalcitrant compounds) tested with respect to their conversion by UPOs, including references to literature data of other oxidoreductases.

Compound	Functional groups $\text{introduced}$ and/or $\text{released}$*	Relative conversion		Oxidases	References
		AaeUPO	MroUPO
Chlorobenzene	−OH (1x, 2x)	+	nt	P450; DIOx	de Bont et al., 1986; Nedelcheva et al., 1998
2-Chlorophenol	−OH (1x, 2x)	+++	nt	LAC; HRP; CPO; LIP; MNP; TYR; VP	Wada et al., 1995; Durán and Esposito, 2000; Zhang et al., 2008; Hibi et al., 2012
1,2-Dichlorobenzene	−OH	+	nt	P450; DIOx	Nedelcheva et al., 1998; Jones et al., 2001; Monferran et al., 2007
1,3-Dichlorobenzene	$-\text{OH}; -\text{Cl}$	++	nt	P450; DIOx	de Bont et al., 1986; Jones et al., 2001
1,4-Dichlorobenzene	−OH	+	nt	P450; DIOx	de Bont et al., 1986; Spiess et al., 1995; Nedelcheva et al., 1998; Jones et al., 2001; Monferran et al., 2007
2,4-Dichlorophenol	−OH	+	+++	LAC; HRP; LIP; DYP; VP; MNP; P450 FMO	Beadle and Smith, 1982; Valli and Gold, 1991; Schomburg and Stephan, 1994; Yee and Wood, 1997; Xu and Bhandari, 2003; Zhang et al., 2008; Fodil et al., 2011; Hibi et al., 2012
1,2,4-Trichlorobenzene	−OH	++	nt	P450; DIOx	van der Meer et al., 1991; Marco-Urrea et al., 2009
2,4,6-Trichlorophenol	$-\text{OH}; -\text{Cl}$	+++	nt	LAC; VP; LIP; MNP; DyP; FMO	Wieser et al., 1997; Reddy et al., 1998; Leontievsky et al., 2001; Fodil et al., 2011; Hibi et al., 2012
Pentachlorophenol	–	0	0	P450; LAC; LIP; MNP; TYR; DYP; VP; FMO	Reddy and Gold, 2000; Thakur et al., 2002; Montiel et al., 2004; Davila-Vazquez et al., 2005; Crawford et al., 2007; Jeon et al., 2008; Fodil et al., 2011
Hexachlorobenzene	–	0	0	P450	Jones et al., 2001
para-Chloro-meta-cresol	$-\text{OH}; -\text{Cl}$	+++	nt	LAC; TYR	Bollag et al., 1988; Freire et al., 2003
2-Chloronaphthalene	−OH (1x, 2x)	+++	nt	P450	Mori et al., 2003
3,3-dichlorobenzidine	−OH	++	nt	P450; FMO	Iba and Thomas, 1988; Imaoka et al., 1997
4-Chlorophenyl phenyl ether	−OH (1x, 2x)	++	nt	P450	Hundt et al., 1999; Hiratsuka et al., 2001
4-Bromophenyl phenyl ether	−OH (1x, 2x)	++	nt	P450	Hundt et al., 1999
3-Chlorophenol**	−OH (1x, 2x)	+++	nt	LAC; HRP; CPO; LIP; MNP; TYR; VP	Wada et al., 1995; Durán and Esposito, 2000; Hibi et al., 2012
4-Chlorophenol**	$-\text{OH} (1\text{x}, 2\text{x}); -\text{Cl}$	+++	nt	LAC; HRP; CPO; LIP; MNP; TYR; DYP; VP	Wada et al., 1995; Durán and Esposito, 2000; Freire et al., 2003; Zhang et al., 2008; Fodil et al., 2011; Hibi et al., 2012; Liers et al., 2014
Nitrobenzene	–	0	nt	BMM; DIOx	Spain, 1995; Lessner et al., 2002; Fishman et al., 2004; Ye et al., 2004
2-Nitrophenol	−OH	+	nt	BMM; FMO; DYP	Ye et al., 2004; Vardar and Wood, 2005; Xiao et al., 2007; Büttner et al., 2015
4-Nitrophenol	−OH	++	nt	BMM; FMO; P450; DYP	Spain, 1995; Amato et al., 1998; Kadiyala and Spain, 1998; Fishman et al., 2004; Ye et al., 2004; Büttner et al., 2015
2,4-Dinitrophenol	–	0	nt	FMO	Cassidy et al., 1999
2,4-Dinitrotoluene	=O	t	nt	DIOx	Spain, 1995; Johnson et al., 2002; Ye et al., 2004
2,6-Dinitrotoluene	–	t	nt	DIOx	Nishino et al., 2000; Ye et al., 2004
4,6-Dinitro-o-cresol	−OH	t	nt	FMO	Cassidy et al., 1999
Benzidine	−OH	t	+	P450; CPO; HRP; LPO; LAC	Phillips and Leonard, 1976; Yamazoe et al., 1988; Lakshmi et al., 1996
1,2-Diphenylhydrazine	−OH	++	nt
bis(2-Ethylhexyl) phthalate	–	0	0	P450	Wittassek and Angerer, 2008
Butyl benzyl phthalate	−OH; = O	+	t
Di-n-butyl phthalate	−OH; = O	+	+	DIOX	Eaton and Ribbons, 1982
Di-n-octyl phthalate	−OH; = O	t	t
Diethyl phthalate	–	0	0
Dimethyl phthalate	–	0	0
Acenaphthylene	−OH (1x, 2x); = O	++	++	LAC; DIOx; P450	Majcherczyk et al., 1998; Pinyakong et al., 2004; Shimada et al., 2015
Acenaphthene	−OH (1x, 2x); = O	++	++	LIP; LAC; DIOx; P450	Vazquez-Duhalt et al., 1994; Majcherczyk et al., 1998; Pinyakong et al., 2004; Shimada et al., 2015
Benzo[a]pyrene	−OH (1x, 2x)	+	++	MNP; LAC; LIP; DIOx; P450	Haemmerli et al., 1986; Warshawsky et al., 1988; Bogan and Lamar, 1995; Sack et al., 1997; Kim et al., 1998; Dodor et al., 2004
Benzo[a]anthracene	−OH (1x, 2x)	++	+	MNP; LAC; LIP; P450	Wood et al., 1976; Bogan and Lamar, 1995; Sack et al., 1997; Majcherczyk et al., 1998
Indeno[1,2,3-cd]pyrene	−OH (1x, 2x)	t	t	LAC	Wu et al., 2008
Benzo[b]fluoranthene	−OH	0	t	LAC; LIP	Bogan and Lamar, 1995; Majcherczyk et al., 1998
Benzo[k]fluoranthene	−OH; (1x, 2x)	t	t	LAC; LIP	Bogan and Lamar, 1995; Majcherczyk et al., 1998
Dibenz[a,h]anthracene		0	0	LAC	Wu et al., 2008
Benzo[g,h,i]perylene		0	0	LAC; LIP	Bogan and Lamar, 1995; Wu et al., 2008
Perylene**	−OH; (1x, 2x)	t	+	LAC	Majcherczyk et al., 1998
9,10-Dihydrophenanthrene**	−OH; (1x, 2x)	t	+
2,4-Dimethylphenol	−OH; = O	+++	nt	FMO; LAC; HRP	Klibanov et al., 1980; Arenghi et al., 2001; Ghosh et al., 2008
Benzene		+		UPO	Karich et al., 2013
Naphthalene		++		UPO	Kluge et al., 2009
Phenol		+++		UPO	Karich et al., 2013
Anisole		+++		UPO	Kinne, 2010
Toluene		+++		UPO	Kinne et al., 2010
Ethylbenzene		+++		UPO	Kluge et al., 2012
Anthracene				UPO	Aranda et al., 2010
Fluorene		+		UPO	Aranda et al., 2010
Phenanthrene		+		UPO	Aranda et al., 2010
Pyrene		+		UPO	Aranda et al., 2010

Evaluation of relative conversion was done according to the following pattern: no conversion (“0”), trace amounts of products detected (“t”), little conversion—well detectable products, decrease of substrate <20% (“+”), moderate conversion—decrease of substrate <50% (“++”), good conversion—decrease of substrate >50% (“+++”);

^*introduced (green) and released functional group (red);

^**not in the EPA priority pollutants list; “nt” not tested”; P450, cytochrome; P-450 monooxygenase; DIOx, Rieske-type dioxygenase; LAC, laccase; TYR, tyrosinase; LIP, lignin peroxidase; MNP, manganese peroxidase; VP, versatile peroxidase; HRP, horseradish peroxidase; CPO, chloroperoxidase; DYP, dye-decolorizing peroxidase; LPO, lactoperoxidase; BMM, bacterial multicomponent monooxygenase; FMO, flavin-dependent monooxygenase (flavoprotein monooxygenase).