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N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ = 4-(dimethylamino)azobenzene + 2 NADPH + 2 H+
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ = 4-(dimethylamino)azobenzene + 2 NADPH + 2 H+
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N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ = 4-(dimethylamino)azobenzene + 2 NADPH + 2 H+
ping-pong mechanism
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N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ = 4-(dimethylamino)azobenzene + 2 NADPH + 2 H+
the catalytic reaction requires tautomerisation of the azo compound to a quinoneimine and provides a unifying mechanism for the reduction of azo substrates by azoreductases
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N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ = 4-(dimethylamino)azobenzene + 2 NADPH + 2 H+
the catalytic reaction requires tautomerisation of the azo compound to a quinoneimine and provides a unifying mechanism for the reduction of azo substrates by azoreductases
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N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ = 4-(dimethylamino)azobenzene + 2 NADPH + 2 H+
the catalytic reaction requires tautomerisation of the azo compound to a quinoneimine and provides a unifying mechanism for the reduction of azo substrates by azoreductases
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N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ = 4-(dimethylamino)azobenzene + 2 NADPH + 2 H+
the catalytic reaction requires tautomerisation of the azo compound to a quinoneimine and provides a unifying mechanism for the reduction of azo substrates by azoreductases
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N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ = 4-(dimethylamino)azobenzene + 2 NADPH + 2 H+
the catalytic reaction requires tautomerisation of the azo compound to a quinoneimine and provides a unifying mechanism for the reduction of azo substrates by azoreductases
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ = 4-(dimethylamino)azobenzene + 2 NADPH + 2 H+
the catalytic reaction requires tautomerisation of the azo compound to a quinoneimine and provides a unifying mechanism for the reduction of azo substrates by azoreductases
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ = 4-(dimethylamino)azobenzene + 2 NADPH + 2 H+
the catalytic reaction requires tautomerisation of the azo compound to a quinoneimine and provides a unifying mechanism for the reduction of azo substrates by azoreductases, mechanism for azoreduction by FMN-dependent azoreductases, overview. N5 of FMN accepts a hydride during oxidation of NAD(P)H and donates it upon reduction of the substrate
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1,2-dimethyl-4(p-carboxyphenylazo)-5-hydroxybenzene + NADPH
1,2-dimethyl-4-amino-5-hydroxybenzene + p-carboxyphenylamine + NADP+
1-(2'-methyl-4'-sulfophenylazo)-2-naphthol + NADH + H+
4-amino-2-methyl-1-benzenesulfonic acid + NAD+ + 1-amino-2-hydroxynaphthalene
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r
1-(2'-methyl-4'-sulfophenylazo)2-naphthol + NAD(P)H
4-amino-2-methyl-1-benzenesulfonic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
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-
?
1-(2'-sulfophenylazo)-2-naphthol + NADH + H+
?
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r
1-(2-pyridylazo)-2-naphthol + NADH + H+
?
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?
1-(2-pyridylazo)-2-naphthol + NADH + H+
? + NAD+
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-
ir
1-(3'-carboxyphenylazo)-2-naphthol + NAD(P)H
3-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
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?
1-(3'-phosphophenylazo)-2-naphthol + NAD(P)H
3-amino-1-benzenephosphate + NAD(P)+ + 1-amino-2-hydroxynaphthalene
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?
1-(3'-sulfophenylazo)-2-naphthol + NAD(P)H
3-amino-1-benzenesulfonic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
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?
1-(4'-carboxyphenylazo)-2-hydroxy-6-carboxynaphthalene + NADH + H+
?
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r
1-(4'-carboxyphenylazo)-2-hydroxy-6-sulfonaphthalene + NAD(P)H
4-carboxyphenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-sulfonaphthalene
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?
1-(4'-carboxyphenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
1-(4'-carboxyphenylazo)-2-naphthol + NADH
4-amino-1-benzoic acid + NAD+ + 1-amino-2-hydroxynaphthalene
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substrate is carboxy-Orange II
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?
1-(4'-carboxyphenylazo)-2-naphthol + NADH + H+
4-aminobenzoate + NAD+ + ?
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i.e. carboxy-Orange II
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r
1-(4'-carboxyphenylazo)-4-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-4-hydroxynaphthalene
1-(4'-nitrophenylazo)-2-hydroxy-6-sulfonaphthalene + NAD(P)H
4-nitrophenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-sulfonaphthalene
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?
1-(4'-phosphophenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzenephosphate + NAD(P)+ + 1-amino-2-hydroxynaphthalene
1-(4'-sulfonaminophenylazo-)2-naphthol + NAD(P)H
4-amino-1-benzenesulfonamine + NAD(P)+ + 1-amino-2-hydroxynaphthalene
1-(4'-sulfophenyl-N-methylhydrazo)-4-naphthol + NADH + H+
?
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i.e. carboxy-Orange I
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r
1-(4'-sulfophenylazo)-2-hydroxy-6-carboxynaphthalene + NAD(P)H
4-sulfophenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-carboxynaphthalene
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?
1-(4'-sulfophenylazo)-2-hydroxy-6-sulfonaphthalene + NAD(P)H
4-sulfophenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-sulfonaphthalene
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?
1-(4'-sulfophenylazo)-4-anthranol + NADH + H+
?
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r
1-(4'-sulfophenylazo)-4-naphthol + NADH + H+
?
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r
1-(4-sulfo-1-naphthylazo)-2-naphthol-3,6-disulfonic acid + NADPH
alpha-naphthylamine-4-sulfonic acid + beta-naphthol-3,6-disulfonic acid + NADP+
1-methyl-1-([1-[(Z)-(methyl[4-[(E)-2-[6'-[(E)-[4-[methyl([4-[(1-methylpyrrolidinium-1-yl)methyl]-1H-1,2,3-triazol-1-yl]methyl)amino]phenyl]diazenyl]-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthen]-3'-yl]ethenyl]phenyl]iminio)methyl]-1H-1,2,3-triazol-4-yl]methyl)pyrrolidinium + FMN + NADH + H+
? + NAD+
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pro-fluorophore, based on fluorescent rhodamine 110. Upon reduction of the two diazo bonds, substrate shows a green fluorescence suitable for the detection of azoreductases
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?
1-phenylazo-2-hydroxy-6-carboxynaphthalene + NAD(P)H
phenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-carboxynaphthalene
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?
1-phenylazo-2-hydroxy-6-sulfonaphthalene + NAD(P)H
phenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-sulfonaphthalene
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?
2 ferricyanide + NADPH
2 ferrocyanide + NADP+ + H+
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?
2'-carboxy-4-N,N-dimethylazobenzene + NAD(P)H
2-carboxy-1-phenylamine + N,N-dimethyl-1,4-phenylenediamine + NADP+
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trivial name methyl red
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?
2,2'-(1,8-dihydroxy-3,6-disulfonaphthalene-2,7-bis-azo)-bis(benzenearsonic acid) + NAD(P)H
?
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reduced to an anion free radical by an outer membrane azoreductase
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?
2-hydroxy-1,4-naphthoquinone + NADH + H+
?
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?
2-hydroxy-1,4-naphthoquinone + NADPH + H+
?
lawsone, quinone reductase activity
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?
2-methyl-1,4-benzoquinone + NADH + H+
?
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?
2-methyl-1,4-naphthoquinone + NADH + H+
?
menadione, vitamin K3
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?
2-methyl-1,4-naphthoquinone + NADPH + H+
?
menadione, quinone reductase activity
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?
2-[4-(dimethylamino)phenylazo]benzoic acid + NADH
2-aminobenzoic acid + N,N-dimethyl-1,4-phenylenediamine + NAD+
2-[4-(dimethylamino)phenylazo]benzoic acid + NADPH
N,N-dimethyl-p-phenylenediamine + 2-aminobenzoic acid + NADP+
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?
3-methyl-4-(2-chlorophenylhydrazone)-isoxazol-5-one + NAD(P)H
o-chloroaniline + ?
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fungicide, trivial name drazoxolon, 90-80% activity with NADH
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?
4'-diethylaminoazobenzene-2-carboxylic acid + NADH + H+
?
ethyl red
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?
4'-dimethylaminoazobenzene-2-carboxylic acid + NADH + H+
2-aminobenzoic acid + N,N'-dimethyl-p-phenylenediamine + NAD+
methyl red
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?
4-(4-aminophenylazo)benzenesulfonic acid + NADPH + H+
?
about 25% specific activity compared to balsalazide
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?
4-(4-nitrophenylazo)-1-naphthol + NAD(P)H
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
4-(dimethylamino)azobenzene + NADPH + H+
N,N-dimethyl-1,4-phenylenediamine + aniline + NADP+
4-([4-(dimethylamino)phenyl]diazenyl)benzene-1-sulfonate + NADPH + H+
? + NADP+
4-dimethylaminoazobenzene-2'-carboxylic acid + 2 NADH + 2 H+
anthranilate + N,N'-dimethylaminoaniline + 2 NAD+
4-dimethylaminoazobenzene-2'-carboxylic acid + 2 NADPH + 2 H+
anthranilate + N,N'-dimethylamino-aniline + 2 NADP+
i.e. methyl red
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?
4-[(2-hydroxy-1-naphthalenyl)azo]benzene sulfonic acid + NAD(P)H
4-amino-1-benzenesulfonic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
4-[(4-hydroxy-1-naphthalenyl)azo]benzene sulfonic acid + NAD(P)H
4-amino-benzenesulfonic acid + 1-amino-4-hydroxynaphthalene + NADP+
Acid Orange 52 + NADPH + H+
?
acid Orange 7 + NAD(P)H
?
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reduces also Acid Orange 6, 8 and 12, Acid Red 88 and 151, NADH is more effective
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?
acid orange 8 + NADH + H+
?
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r
Acid Red 1 + NADPH + H+
?
acid red 119 + NADH + H+
? + NAD+
Acid Red 14 + NADPH + H+
?
acid red 151 + NADH + H+
?
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r
acid red 88 + NAD(P)H + H+
?
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?
acid red 88 + NADH + H+
?
acid red 88 + NADH + H+
? + NAD+
Acid Red 88 + NADPH + H+
?
acid red 88 + NADPH + H+
? + NADP+
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?
acid yellow 19 + NADPH + H+
? + NADP+
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low activity
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?
Acid Yellow 23 + NADPH + H+
?
Amaranth + NADPH
? + NADP+
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?
amaranth + NADPH + H+
?
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r
Amido black + NADH
?
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?
anthraquinone-2,6-disulfonate + NADH + H+
?
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?
anthraquinone-2,6-disulfonate + NADPH + H+
?
quinone reductase activity
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?
anthraquinone-2-sulfonate + NADH + H+
?
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?
anthraquinone-2-sulfonate + NADPH + H+
?
quinone reductase activity
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?
Atul acid black + NADH
?
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-
-
?
balsalazide + NADPH + H+
?
100% specific activity
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?
balsalazide + NADPH + H+
? + NADP+
tautomeric forms of balsalazide occur in solution, reaction mechanism, overview
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?
balsalzide + NADH + H+
? + NAD+
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?
BHQ-10 + NADPH + H+
? + NADP+
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?
Cibacron Marine + NADPH + H+
?
Cibacron Marine dye + NADPH + H+
? + NADP+
reductive degradation
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r
congo red + NAD(P)H + H+
?
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?
Congo red + NADH + H+
? + NAD+
Cr(VI) + NADPH + H+
Cr(III) + NADP+
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r
di-sodium-(R)-benzyl-azo-2,7-dihydroxy-3,6-disulfonyl-naphthaline + NADH
?
direct blue 14 + ?
o-tolidine + ?
direct blue 15 + FAD + NADH + H+
? + NAD+
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highest activity in presence of both NADH and FAD
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?
direct blue 15 + NAD(P)H
3,3'-dimethoxybenzidine + 1-hydroxy-2,8-diamino-3,6-naphthalenedisulfonic acid + NAD(P)+
direct blue 15 + NAD(P)H + H+
?
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?
direct blue 15 + NADH + H+
? + NAD+
Direct Brown 44 + NADPH + H+
?
direct red 28 + NADH + H+
benzidine + 4-aminobiphenyl + NAD+
Direct Red 80 + NADPH + H+
?
direct red 81 + NADPH + H+
? + NADP+
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-
?
disperse orange 3 + NADPH + H+
? + NADP+
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-
?
Disperse yellow + NADH
?
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85% of the activity with Methyl red
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-
?
Eriochrome blue black + NADH
?
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1.7.1.6 azobenzene reductase
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