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Information on EC 1.7.1.6 - azobenzene reductase
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1.7.1.6 azobenzene reductaseIUBMB Comments
The reaction occurs in the reverse direction to that shown above. Other azo dyes, such as Methyl Red, Rocceline, Solar Orange and Sumifix Black B can also be reduced .
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Word Map
- 1.7.1.6
-
decolor
-
textile
-
veratryl
- laccase
- environmental protection
- drug development
-
remazol
-
voltammograms
- dehydrochlorinase
- 2,6-dinitrotoluene
- industry
-
dechlorinase
-
rubine
- laterosporus
-
ponceau
- dcip
- degradation
- analysis
The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Reaction Schemes
Synonyms
acpD, aerobic azoreductase, Azo 1, azo dye reductase, azo reductase, azo-dye reductase, AzoA, AzoB, AzoC, AzoEF1, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
acpD
aerobic azoreductase
azo reductase
AzoA
AzoB
AzoEF1
AzoI
AzoII
AzoR
AzoR1
azoreductase
AZR
AzrA
AzrC
AzrS
class 1 azoreductase
class 2 azoreductase
FMN-dependent NAD(P)H azoreductase
FMN-dependent NADH-azo compound oxidoreductase
FMN-dependent NADH-azoreductase
NADH driven FMN dependent azoreductase
NADH-azoreductase
NADPH-dependent azoreductase Azr
Orange I azoreductase
PpAzoR
SO 4396
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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+
-
-
-
-
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ = 4-(dimethylamino)azobenzene + 2 NADPH + 2 H+
ping-pong mechanism
-
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
-
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
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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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
reduction
reduction
-
catalyzes the reductive cleavage of azo groups by a ping-pong mechanism
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SYSTEMATIC NAME
IUBMB Comments
N,N-dimethyl-1,4-phenylenediamine, aniline:NADP+ oxidoreductase
The reaction occurs in the reverse direction to that shown above. Other azo dyes, such as Methyl Red, Rocceline, Solar Orange and Sumifix Black B can also be reduced [2].
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CAS REGISTRY NUMBER
COMMENTARY
9029-31-6
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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
-
-
-
-
r
1-(2'-methyl-4'-sulfophenylazo)2-naphthol + NAD(P)H
4-amino-2-methyl-1-benzenesulfonic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
-
-
-
?
1-(2-pyridylazo)-2-naphthol + NADH + H+
? + NAD+
-
-
-
ir
1-(3'-carboxyphenylazo)-2-naphthol + NAD(P)H
3-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
-
-
-
?
1-(3'-phosphophenylazo)-2-naphthol + NAD(P)H
3-amino-1-benzenephosphate + NAD(P)+ + 1-amino-2-hydroxynaphthalene
-
-
-
?
1-(3'-sulfophenylazo)-2-naphthol + NAD(P)H
3-amino-1-benzenesulfonic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
-
-
-
?
1-(4'-carboxyphenylazo)-2-hydroxy-6-carboxynaphthalene + NADH + H+
?
-
-
-
-
r
1-(4'-carboxyphenylazo)-2-hydroxy-6-sulfonaphthalene + NAD(P)H
4-carboxyphenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-sulfonaphthalene
-
-
-
?
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
-
substrate is carboxy-Orange II
-
-
?
1-(4'-carboxyphenylazo)-2-naphthol + NADH + H+
4-aminobenzoate + NAD+ + ?
-
i.e. carboxy-Orange II
-
-
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
-
-
-
?
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+
?
-
i.e. carboxy-Orange I
-
-
r
1-(4'-sulfophenylazo)-2-hydroxy-6-carboxynaphthalene + NAD(P)H
4-sulfophenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-carboxynaphthalene
-
-
-
?
1-(4'-sulfophenylazo)-2-hydroxy-6-sulfonaphthalene + NAD(P)H
4-sulfophenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-sulfonaphthalene
-
-
-
?
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+
-
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
-
-
?
1-phenylazo-2-hydroxy-6-carboxynaphthalene + NAD(P)H
phenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-carboxynaphthalene
-
-
-
?
1-phenylazo-2-hydroxy-6-sulfonaphthalene + NAD(P)H
phenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-sulfonaphthalene
-
-
-
?
2'-carboxy-4-N,N-dimethylazobenzene + NAD(P)H
2-carboxy-1-phenylamine + N,N-dimethyl-1,4-phenylenediamine + NADP+
-
trivial name methyl red
-
?
2,2'-(1,8-dihydroxy-3,6-disulfonaphthalene-2,7-bis-azo)-bis(benzenearsonic acid) + NAD(P)H
?
-
reduced to an anion free radical by an outer membrane azoreductase
-
-
?
2-hydroxy-1,4-naphthoquinone + NADPH + H+
?
lawsone, quinone reductase activity
-
-
?
2-methyl-1,4-naphthoquinone + NADH + H+
?
menadione, vitamin K3
-
-
?
2-methyl-1,4-naphthoquinone + NADPH + H+
?
menadione, quinone reductase activity
-
-
?
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+
-
-
-
-
?
3-methyl-4-(2-chlorophenylhydrazone)-isoxazol-5-one + NAD(P)H
o-chloroaniline + ?
-
fungicide, trivial name drazoxolon, 90-80% activity with NADH
-
?
4'-diethylaminoazobenzene-2-carboxylic acid + NADH + H+
?
ethyl red
-
-
?
4'-dimethylaminoazobenzene-2-carboxylic acid + NADH + H+
2-aminobenzoic acid + N,N'-dimethyl-p-phenylenediamine + NAD+
methyl red
-
-
?
4-(4-aminophenylazo)benzenesulfonic acid + NADPH + H+
?
about 25% specific activity compared to balsalazide
-
-
?
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-dimethylaminoazobenzene-2'-carboxylic acid + NADH + H+
anthranilate + N,N'-dimethylaminoaniline + NAD+
4-dimethylaminoazobenzene-2'-carboxylic acid + NADPH + H+
anthranilate + N,N'-dimethylamino-aniline + NAD+
i.e. methyl red
-
-
?
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 7 + NAD(P)H
?
-
reduces also Acid Orange 6, 8 and 12, Acid Red 88 and 151, NADH is more effective
-
-
?
anthraquinone-2,6-disulfonate + NADPH + H+
?
quinone reductase activity
-
-
?
anthraquinone-2-sulfonate + NADPH + H+
?
quinone reductase activity
-
-
?
balsalazide + NADPH + H+
? + NADP+
tautomeric forms of balsalazide occur in solution, reaction mechanism, overview
-
-
?
direct blue 15 + FAD + NADH + H+
? + NAD+
-
highest activity in presence of both NADH and FAD
-
-
?
direct blue 15 + NAD(P)H
3,3'-dimethoxybenzidine + 1-hydroxy-2,8-diamino-3,6-naphthalenedisulfonic acid + NAD(P)+
ethyl red + NADH + H+
? + NAD+
best substrate, 182% of the activity with methyl red at 30°C
-
-
ir
methyl red + NADH
2-aminobenzoic acid + N,N-dimethyl-1,4-phenylenediamine + NAD+
-
-
-
-
?
methyl red + NADH + H+
2-aminobenzoic acid + N,N-dimethyl-1,4-phenylenediamine + NAD+
-
-
-
-
r
methyl red + NADH + H+
anthranilate + N,N-dimethyl-1,4-phenylenediamine + NAD+
-
-
-
r
methyl red + NADH + H+
N,N-dimethyl-p-phenylenediamine and 2-aminobenzoic acid + NAD+
A0A4V6LLF0
-
-
-
?
methyl red + NADH + H+
o-aminobenzoic acid + N,N'-dimethyl-p-phenylenediamine + NAD+
-
-
-
ir
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+
4-(dimethylamino)azobenzene + 2 NADPH + 2 H+
NADPH + 9,10-phenanthrenequinone
NADP+ + 9,10-phenanthrenequinol
-
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NADPH + oxidized cytochrome c
NADP+ + reduced cytochrome c
-
in the presence of menadione as electron carrier
-
?
naphthol blue black + NADH + H+
? + NAD+
-
78% conversion, analysis by UV-visible and FITR spectroscopy, HPLC, and GC-MS
-
-
?
Navitan fast blue S5R + NADH
metanilic acid + 1,4-diamino naphtalene + peri acid + NAD+
-
-
-
-
?
olsalazine + NADPH + H+
?
less than 10% specific activity compared to balsalazide
-
-
?
orange II + NADH + H+
sulfanilic acid + 1-amino-2-naphthol + NAD+
-
-
-
-
?
reactive violet 5 + NADH + H+
? + NAD+
-
-
-
?
reactive violet 5 + NADPH + H+
? + NADP+
-
-
-
?
sulfasalazine + NADPH + H+
?
about 20% specific activity compared to balsalazide
-
-
?
1,2-dimethyl-4(p-carboxyphenylazo)-5-hydroxybenzene + NADPH
1,2-dimethyl-4-amino-5-hydroxybenzene + p-carboxyphenylamine + NADP+
-
-
-
?
1,2-dimethyl-4(p-carboxyphenylazo)-5-hydroxybenzene + NADPH
1,2-dimethyl-4-amino-5-hydroxybenzene + p-carboxyphenylamine + NADP+
-
-
-
?
1,2-dimethyl-4(p-carboxyphenylazo)-5-hydroxybenzene + NADPH
1,2-dimethyl-4-amino-5-hydroxybenzene + p-carboxyphenylamine + NADP+
-
-
-
?
1,2-dimethyl-4(p-carboxyphenylazo)-5-hydroxybenzene + NADPH
1,2-dimethyl-4-amino-5-hydroxybenzene + p-carboxyphenylamine + NADP+
-
-
-
?
1,2-dimethyl-4(p-carboxyphenylazo)-5-hydroxybenzene + NADPH
1,2-dimethyl-4-amino-5-hydroxybenzene + p-carboxyphenylamine + NADP+
-
-
-
?
1-(4'-carboxyphenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
substrate is carboxy-Orange II
-
-
?
1-(4'-carboxyphenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
Luteovulum sphaeroides AS1.1737
substrate is carboxy-Orange II
-
-
?
1-(4'-carboxyphenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
-
-
-
?
1-(4'-carboxyphenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
-
-
-
?
1-(4'-carboxyphenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
substrate can be utilized as sole carbon and energy source
-
-
?
1-(4'-carboxyphenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
substrate is carboxy-Orange II
-
-
?
1-(4'-carboxyphenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
Xenophilus azovorans KF46F / DSM 13620
substrate can be utilized as sole carbon and energy source
-
-
?
1-(4'-carboxyphenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
Xenophilus azovorans KF46F / DSM 13620
substrate is carboxy-Orange II
-
-
?
1-(4'-carboxyphenylazo)-4-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-4-hydroxynaphthalene
substrate can be utilized as sole carbon and energy source
-
-
?
1-(4'-carboxyphenylazo)-4-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-4-hydroxynaphthalene
substrate is carboxy-Orange I
-
-
?
1-(4'-carboxyphenylazo)-4-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-4-hydroxynaphthalene
substrate can be utilized as sole carbon and energy source
-
-
?
1-(4'-carboxyphenylazo)-4-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-4-hydroxynaphthalene
substrate is carboxy-Orange I
-
-
?
1-(4'-carboxyphenylazo)-4-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-4-hydroxynaphthalene
-
-
-
-
?
1-(4'-carboxyphenylazo)-4-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-4-hydroxynaphthalene
-
-
-
-
?
1-(4'-phosphophenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzenephosphate + NAD(P)+ + 1-amino-2-hydroxynaphthalene
-
-
-
?
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'-sulfonaminophenylazo-)2-naphthol + NAD(P)H
4-amino-1-benzenesulfonamine + NAD(P)+ + 1-amino-2-hydroxynaphthalene
-
-
-
?
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-(4-sulfo-1-naphthylazo)-2-naphthol-3,6-disulfonic acid + NADPH
alpha-naphthylamine-4-sulfonic acid + beta-naphthol-3,6-disulfonic acid + NADP+
-
-
-
?
1-(4-sulfo-1-naphthylazo)-2-naphthol-3,6-disulfonic acid + NADPH
alpha-naphthylamine-4-sulfonic acid + beta-naphthol-3,6-disulfonic acid + NADP+
-
activity in liver microsomes, reduces also the dyes Red 2G, Red 10B, Carmoisine and Ponceau 4R
-
?
1-(4-sulfo-1-naphthylazo)-2-naphthol-3,6-disulfonic acid + NADPH
alpha-naphthylamine-4-sulfonic acid + beta-naphthol-3,6-disulfonic acid + NADP+
-
trivial name amaranth, activity in liver microsomes
-
?
2-[4-(dimethylamino)phenylazo]benzoic acid + NADH
2-aminobenzoic acid + N,N-dimethyl-1,4-phenylenediamine + NAD+
-
substrate is Methyl red
-
-
?
2-[4-(dimethylamino)phenylazo]benzoic acid + NADH
2-aminobenzoic acid + N,N-dimethyl-1,4-phenylenediamine + NAD+
substrate is Methyl red
-
-
?
2-[4-(dimethylamino)phenylazo]benzoic acid + NADH
2-aminobenzoic acid + N,N-dimethyl-1,4-phenylenediamine + NAD+
Luteovulum sphaeroides AS1.1737
substrate is Methyl red
-
-
?
2-[4-(dimethylamino)phenylazo]benzoic acid + NADH
2-aminobenzoic acid + N,N-dimethyl-1,4-phenylenediamine + NAD+
-
substrate is Methyl red
-
-
?
4-(4-nitrophenylazo)-1-naphthol + NAD(P)H
?
substrate is Magneson II, 13% of the activity with carboxy-Orange I
-
-
?
4-(4-nitrophenylazo)-1-naphthol + NAD(P)H
?
substrate is Magneson II, 13% of the activity with carboxy-Orange I
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
Orange I azoreductase: absolute requirement for a hydroxyl group in 4'-position of the naphthol ring of the substrate molecule
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
Orange II azoreductase: requirement for substrates with a 2-naphthol moiety
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
Orange II azoreductase: requirement for substrates with a 2-naphthol moiety
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
key enzyme of azo dye degradation, selective agent during experimental evolution in continuous cultures
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
Orange I azoreductase: absolute requirement for a hydroxyl group in 4'-position of the naphthol ring of the substrate molecule
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
Orange II azoreductase: requirement for substrates with a 2-naphthol moiety
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
key enzyme of azo dye degradation, selective agent during experimental evolution in continuous cultures
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
Orange II azoreductase: requirement for substrates with a 2-naphthol moiety
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
specific for reduction of methyl red
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
electron transport protein
-
?
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-(dimethylamino)azobenzene + NADPH + H+
N,N-dimethyl-1,4-phenylenediamine + aniline + NADP+
-
-
-
-
?
4-([4-(dimethylamino)phenyl]diazenyl)benzene-1-sulfonate + NADPH + H+
? + NADP+
-
i.e. methyl orange
-
-
?
4-([4-(dimethylamino)phenyl]diazenyl)benzene-1-sulfonate + NADPH + H+
? + NADP+
-
i.e. methyl orange
-
-
?
4-dimethylaminoazobenzene-2'-carboxylic acid + NADH + H+
anthranilate + N,N'-dimethylaminoaniline + NAD+
i.e. methyl red
-
-
?
4-dimethylaminoazobenzene-2'-carboxylic acid + NADH + H+
anthranilate + N,N'-dimethylaminoaniline + NAD+
-
i.e. methyl red
-
-
?
4-dimethylaminoazobenzene-2'-carboxylic acid + NADH + H+
anthranilate + N,N'-dimethylaminoaniline + NAD+
Shewanella oneidensis MR-1 / ATCC 700550
-
i.e. methyl red
-
-
?
4-[(2-hydroxy-1-naphthalenyl)azo]benzene sulfonic acid + NAD(P)H
4-amino-1-benzenesulfonic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
-
NADH is more effective
-
?
4-[(2-hydroxy-1-naphthalenyl)azo]benzene sulfonic acid + NAD(P)H
4-amino-1-benzenesulfonic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
-
trivial name Orange II
-
?
4-[(2-hydroxy-1-naphthalenyl)azo]benzene sulfonic acid + NAD(P)H
4-amino-1-benzenesulfonic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
-
trivial name Orange II
-
?
4-[(4-hydroxy-1-naphthalenyl)azo]benzene sulfonic acid + NAD(P)H
4-amino-benzenesulfonic acid + 1-amino-4-hydroxynaphthalene + NADP+
-
trivial name Orange I
-
?
4-[(4-hydroxy-1-naphthalenyl)azo]benzene sulfonic acid + NAD(P)H
4-amino-benzenesulfonic acid + 1-amino-4-hydroxynaphthalene + NADP+
-
trivial name Orange I
-
?
acid red 88 + NADH + H+
? + NAD+
10% of hte activity with methyl red at 30°C
-
-
ir
di-sodium-(R)-benzyl-azo-2,7-dihydroxy-3,6-disulfonyl-naphthaline + NADH
?
-
-
-
-
?
di-sodium-(R)-benzyl-azo-2,7-dihydroxy-3,6-disulfonyl-naphthaline + NADH
?
-
-
-
-
?
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
3,3'-dimethoxybenzidine + 1-hydroxy-2,8-diamino-3,6-naphthalenedisulfonic acid + NAD(P)+
-
-
-
?
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
3,3'-dimethoxybenzidine + 1-hydroxy-2,8-diamino-3,6-naphthalenedisulfonic acid + NAD(P)+
-
-
-
?
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
3,3'-dimethoxybenzidine + 1-hydroxy-2,8-diamino-3,6-naphthalenedisulfonic acid + NAD(P)+
-
-
-
?
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
3,3'-dimethoxybenzidine + 1-hydroxy-2,8-diamino-3,6-naphthalenedisulfonic acid + NAD(P)+
-
-
-
?
direct red 28 + NADH + H+
benzidine + 4-aminobiphenyl + NAD+
-
-
-
?
direct red 28 + NADH + H+
benzidine + 4-aminobiphenyl + NAD+
-
-
-
?
methyl red + NADH + H+
?
the enzyme exhibits lower activity with NADH compared to NADPH
-
-
?
methyl red + NADH + H+
anthranilate + N,N'-dimethylaminoaniline + NAD+
i.e. 4-dimethylaminoazobenzene-2'-carboxylic acid
-
-
?
methyl red + NADH + H+
anthranilate + N,N'-dimethylaminoaniline + NAD+
Shewanella oneidensis MR-1 / ATCC 700550
i.e. 4-dimethylaminoazobenzene-2'-carboxylic acid
-
-
?
methyl red + NADH + H+
anthranilate + N,N'-dimethylaminoaniline + NAD+
i.e. 4-dimethylaminoazobenzene-2'-carboxylic acid
-
-
?
methyl red + NADH + H+
anthranilate + N,N'-dimethylaminoaniline + NAD+
i.e. 4-dimethylaminoazobenzene-2'-carboxylic acid
-
-
?
methyl red + NADPH + H+
?
about 50% specific activity compared to balsalazide
-
-
?
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+
-
-
-
?
Orange I + NADH
?
both NADH and NADPH can be used as an electron donor for its activity with 4-(4-hydroxy-1-naphthylazo)benzenesulfonic acid (Orange I) as substrate
-
-
?
Orange I + NADH
?
both NADH and NADPH can be used as an electron donor for its activity with 4-(4-hydroxy-1-naphthylazo)benzenesulfonic acid (Orange I) as substrate
-
-
?
Orange I + NADPH
?
both NADH and NADPH can be used as an electron donor for its activity with 4-(4-hydroxy-1-naphthylazo)benzenesulfonic acid (Orange I) as substrate
-
-
?
Orange I + NADPH
?
both NADH and NADPH can be used as an electron donor for its activity with 4-(4-hydroxy-1-naphthylazo)benzenesulfonic acid (Orange I) as substrate
-
-
?
oxidized methyl red + NADH + H+
reduced methyl red + NAD+
-
-
-
-
?
oxidized methyl red + NADH + H+
reduced methyl red + NAD+
-
-
-
-
?
additional information
?
-
-
Basic violet 3, Basic Red 9, Acid Blue 74, Acid blue 225, and Disperse red 86 are not metabolized
-
-
?
additional information
?
-
-
several derivatives of di-sodium-(R)-benzyl-azo-2,7-dihydroxy-3,6-disulfonyl-naphthaline tested as substrates are found to be metabolized
-
-
?
additional information
?
-
-
Basic violet 3, Basic Red 9, Acid Blue 74, Acid blue 225, and Disperse red 86 are not metabolized
-
-
?
additional information
?
-
-
several derivatives of di-sodium-(R)-benzyl-azo-2,7-dihydroxy-3,6-disulfonyl-naphthaline tested as substrates are found to be metabolized
-
-
?
additional information
?
-
-
enzyme AzrC interacts with azo dyes orange G, acid red 88, Sudan I, orange I, and methyl red. The hydrophobic azo dyes like acid red 88 binds more tightly to the AzrC protein
-
-
?
additional information
?
-
in general, the substrates of azoreductases do not make many specific hydrophilic interactions, which explains the ability of the active site to accommodate a range of hydrophobic substrates
-
-
?
additional information
?
-
-
in general, the substrates of azoreductases do not make many specific hydrophilic interactions, which explains the ability of the active site to accommodate a range of hydrophobic substrates
-
-
?
additional information
?
-
-
important for the conversion of azo dyes in the gastrointestinal tract
-
-
?
additional information
?
-
-
in general, the substrates of azoreductases do not make many specific hydrophilic interactions, which explains the ability of the active site to accommodate a range of hydrophobic substrates
-
-
?
additional information
?
-
the enzyme can also catalyze the nitroreduction of 7-nitrocoumarin-3-carboxylic acid in a FMN-dependent manner
-
-
?
additional information
?
-
-
the enzyme can also catalyze the nitroreduction of 7-nitrocoumarin-3-carboxylic acid in a FMN-dependent manner
-
-
?
additional information
?
-
-
no substrates: ponceau S, tartrazine, amaranth
-
-
?
additional information
?
-
no substrates: ponceau S, tartrazine, amaranth
-
-
?
additional information
?
-
-
no substrates: ponceau S, tartrazine, amaranth
-
-
?
additional information
?
-
-
the enzyme from strain L2 decolorizes a wide spectrum of azo dyes with a constantly high activity, overview
-
-
?
additional information
?
-
-
the enzyme from strain L2 decolorizes a wide spectrum of azo dyes with a constantly high activity, overview
-
-
?
additional information
?
-
-
enzyme additionally shows quinone reductase activity. When NAD(P)H is used as an electron donor, the purified enzyme can reduce menadione effectively with a quinone reductase activity of approximately 3.4 U ml-1
-
-
?
additional information
?
-
-
in general, the substrates of azoreductases do not make many specific hydrophilic interactions, which explains the ability of the active site to accommodate a range of hydrophobic substrates
-
-
?
additional information
?
-
-
enzyme additionally shows quinone reductase activity. When NAD(P)H is used as an electron donor, the purified enzyme can reduce menadione effectively with a quinone reductase activity of approximately 3.4 U ml-1
-
-
?
additional information
?
-
-
in general, the substrates of azoreductases do not make many specific hydrophilic interactions, which explains the ability of the active site to accommodate a range of hydrophobic substrates
-
-
?
additional information
?
-
Methyl Red, Amaranth, Ponceau BS, Ponceau S, Orange II, Orange G, Megneson II, 1-(4-nitrophenylazo)-2-naphthol, and 4-(4-nitrophenylazo)-resorcinol are not reduced by AzoB
-
-
?
additional information
?
-
Methyl Red, Amaranth, Ponceau BS, Ponceau S, Orange II, Orange G, Megneson II, 1-(4-nitrophenylazo)-2-naphthol, and 4-(4-nitrophenylazo)-resorcinol are not reduced by AzoB
-
-
?
additional information
?
-
no activity with Amaranth, Tropaeolin, Orange II, Ponceau S, Ponceau BS, and Orange G
-
-
?
additional information
?
-
-
no activity with Amaranth, Tropaeolin, Orange II, Ponceau S, Ponceau BS, and Orange G
-
-
?
additional information
?
-
in general, the substrates of azoreductases do not make many specific hydrophilic interactions, which explains the ability of the active site to accommodate a range of hydrophobic substrates
-
-
?
additional information
?
-
-
in general, the substrates of azoreductases do not make many specific hydrophilic interactions, which explains the ability of the active site to accommodate a range of hydrophobic substrates
-
-
?
additional information
?
-
-
the bifunctional enzyme shows activity with quinone substrates, anthraquinone-2-sulfonic acid, 1,4-benzoquinone, 1,2-dihydroxybenzene (catechol), 2-hydroxy-1,4-naphthoquinone (Lawsone), and 1,2-naphthoquinone-4-sulfonate, and NADPH as cofactor, cf. EC 1.6.5.10
-
-
?
additional information
?
-
-
generation of a coupled enzyme system constructed with azoreductase and glucose 1-dehydrogenase for removal of methyl red, method evaluation, overview. Artificial neural network modelling of the integrated enzyme system
-
-
?
additional information
?
-
Shewanella oneidensis MR-1 / ATCC 700550
-
generation of a coupled enzyme system constructed with azoreductase and glucose 1-dehydrogenase for removal of methyl red, method evaluation, overview. Artificial neural network modelling of the integrated enzyme system
-
-
?
additional information
?
-
-
wide substrate specificity of the enzyme. No activity with reactive blue 4
-
-
?
additional information
?
-
substrate specificity: the catalytic efficiency of AzrS follows the descending order of methyl red, methyl orange, and congo red. The enzyme has a wide substrate range of azo dyes
-
-
?
additional information
?
-
substrate specificity: the catalytic efficiency of AzrS follows the descending order of methyl red, methyl orange, and congo red. The enzyme has a wide substrate range of azo dyes
-
-
?
additional information
?
-
-
does not react with NADH as electron donor
-
-
?
additional information
?
-
ammoniumazo-1, citrus yellow, orange G, Ponceau BS, and ruby red are inert to reduction with BTI1
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1-(4'-carboxyphenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
1-(4'-carboxyphenylazo)-4-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-4-hydroxynaphthalene
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+
additional information
?
-
-
important for the conversion of azo dyes in the gastrointestinal tract
-
-
?
1-(4'-carboxyphenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
substrate can be utilized as sole carbon and energy source
-
-
?
1-(4'-carboxyphenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
Xenophilus azovorans KF46F / DSM 13620
substrate can be utilized as sole carbon and energy source
-
-
?
1-(4'-carboxyphenylazo)-4-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-4-hydroxynaphthalene
substrate can be utilized as sole carbon and energy source
-
-
?
1-(4'-carboxyphenylazo)-4-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-4-hydroxynaphthalene
substrate can be utilized as sole carbon and energy source
-
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
key enzyme of azo dye degradation, selective agent during experimental evolution in continuous cultures
-
?
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
-
key enzyme of azo dye degradation, selective agent during experimental evolution in continuous cultures
-
?
4-(dimethylamino)azobenzene + NADPH + H+
N,N-dimethyl-1,4-phenylenediamine + aniline + NADP+
-
-
-
-
?
4-(dimethylamino)azobenzene + NADPH + H+
N,N-dimethyl-1,4-phenylenediamine + aniline + NADP+
-
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FAD
-
about 60% of the activity in presence of FMN. FAD binds to the apo-form and the bound FAD is stably retained in the enzyme molecule without degradation to FMN. The isoalloxazine ring of FAD localizes at the same site and plays the same role as that of FMN in the enzyme
FMN
enzyme sequence consists of different sites such as FMN-dependent NADH-azoreductase site azoR, residues 2-204, flavodoxin-like fold, residues 2-205, NADPH-dependent FMN reductase, residues 2-205, cAMP and cGMP-dependent protein kinase phosphorylation site
FMN
-
a flavin-dependent azoreductase, FMN is anchored by a series of sequence-independent hydrogen bonds to a structural motif referred to as the FMN binding cradle. One molecule of flavin is bound within each active site and is required for activity
FMN
enzyme-bound prosthetic group, FMN-dependence for azoreductase activity
NADH
180fold preference for NADH over NADPH as an electron donor to reduce methyl red
NADH
-
AzoA shows more than 180fold preference for NADH over NADPH as an electron donor to reduce methyl red
NADH
when NADPH serves as the electron donor, the activity of the enzyme is 63% higher than that when NADH is used
NADH
enzyme sequence consists of different sites such as FMN-dependent NADH-azoreductase site azoR, residues 2-204, flavodoxin-like fold, residues 2-205, NADPH-dependent FMN reductase, residues 2-205, cAMP and cGMP-dependent protein kinase phosphorylation site
NADPH
180fold preference for NADH over NADPH as an electron donor to reduce methyl red
NADPH
-
AzoA shows more than 180fold preference for NADH over NADPH as an electron donor to reduce methyl red
NADPH
when NADPH serves as the electron donor, the activity of the enzyme is 63% higher than that when NADH is used
NADPH
enzyme sequence consists of different sites such as FMN-dependent NADH-azoreductase site azoR, residues 2-204, flavodoxin-like fold, residues 2-205, NADPH-dependent FMN reductase, residues 2-205, cAMP and cGMP-dependent protein kinase phosphorylation site
additional information
-
P-450 type cytochromes are responsible for azoreductase activity
-
additional information
-
apparent non-identity of cytochrome c reductase and flavin-dependent azoreductase activity
-
additional information
-
effect of different cofactors on azoreductase activity of intestinal anaerobic bacteria
-
additional information
-
effect of different cofactors on azoreductase activity of intestinal anaerobic bacteria
-
additional information
-
effect of different cofactors on azoreductase activity of intestinal anaerobic bacteria
-
additional information
-
effect of different cofactors on azoreductase activity of intestinal anaerobic bacteria
-
additional information
-
effect of different cofactors on azoreductase activity of intestinal anaerobic bacteria
-
additional information
-
effect of different cofactors on azoreductase activity of intestinal anaerobic bacteria
-
additional information
-
effect of different cofactors on azoreductase activity of intestinal anaerobic bacteria
-
additional information
-
effect of different cofactors on azoreductase activity of intestinal anaerobic bacteria
-
additional information
-
effect of different cofactors on azoreductase activity of intestinal anaerobic bacteria
-
additional information
AzoB belongs to the flavin-free azoreductase group
-
additional information
-
the flavin mononucleotide analogue roseoflavin mononucleotide binds to the AzoR apoenzyme with an even higher affinity compared to that of the natural cofactor FMN. Roseoflavin mononucleotide binding does not affect the overall topology of the enzyme and also does not interfere with dimerization of AzoR. The AzoR-roseoflavin mononucleotide holoenzyme complex shows 30% of AzoR-FMN activity in a standard assay
-
additional information
AzrS shows activity with both NADH and NADPH. The maximum relative activity of AzrS with 0.875 mM NADPH or NADH is 28.1% and 100%, respectively, indicating that AzrS shows a preference for NADH rather than NADPH
-
additional information
the enzyme can use both cofactors, NADH and NADPH, it shows a preference towards NADH for the azoreductase activity, but a preference towards NADPH for the nitroreductase activity
-
additional information
-
the enzyme can use both cofactors, NADH and NADPH, it shows a preference towards NADH for the azoreductase activity, but a preference towards NADPH for the nitroreductase activity
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ca2+
Fe3+
Mg2+
Zn2+
Mg2+
activation, optimum concentration 25 mM giving 126% of initial activity
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
ferric chloride
-
1 mM leads to 80% inhibition, 2.5 mM leads to 98% inhibition
dicoumarol
-
0.0001 mM, 50% inhibition of methyl red reduction, 0.0004 mM, 90% inhibition, competitive vs. NADPH noncompetitve vs. methyl red
additional information
-
not inhibited by N-ethylmaleimide, p-chloromercuribenzoate and monoiodoacetic acid
-
additional information
-
0.08% SDS together with 0.0022 mM KCN causes 50% inhibition
-
additional information
-
changes in salinity from 0 to 2% do not affect the activity of the enzyme very much. After a 1-h incubation, more than 80% relative activity is indicated at 0-5% salt concentrations
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2-methylhydroquinone
0.5 mM, increase in expression of azoR mRNA relative to the expression at zero time before stress is applied, at 10 min 46.0, at 20 min 129.1
catechol
6 mM, increase in expression of azoR mRNA relative to the expression at zero time before stress is applied, at 10 min 15.6, at 20 min 31.9
Diamide
1 mM, increase in expression of azoR mRNA relative to the expression at zero time before stress is applied, at 10 min 11.4, at 20 min 8.1
H2O2
1 mM, increase in expression of azoR mRNA relative to the expression at zero time before stress is applied, at 10 min 0.9, at 20 min 0.6, 10 mM, 10 min 3.0, 20 min 1.9
menadione
0.3 mM, increase in expression of azoR mRNA relative to the expression at zero time before stress is applied, at 10 min 25.5, at 20 min 13.3
additional information
-
the enzyme is stimulated on the addition of flavin or quinone compounds. Supplementation of the azoreductase assay with redox active substances (riboflavin, anthraquinone-2,6-disulfonic acid, and anthraquinone-2-sulfonic acid) increases the specific activity of membrane-bound azoreductase as the shuttling of electrons to azo substrate is promoted
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Colitis, Ulcerative
Intestinal luminal pH in inflammatory bowel disease: possible determinants and implications for therapy with aminosalicylates and other drugs.
Inflammatory Bowel Diseases
Molecular Cloning, Characterisation and Ligand-bound Structure of an Azoreductase from Pseudomonas aeruginosa.
Inflammatory Bowel Diseases
Role of tyrosine 131 in the active site of paAzoR1, an azoreductase with specificity for the inflammatory bowel disease prodrug balsalazide.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.005
Direct blue 15
-
pH not specified in the publication, temperature not specified in the publication
0.00018
FAD
-
pH not specified in the publication, temperature not specified in the publication
0.057
2-[4-(dimethylamino)phenylazo]benzoic acid
-
in 25 mM potassium phosphate buffer (pH 7.1), 0.25 mM 2-[4-(dimethylamino)phenylazo]benzoic acid and 0.1 mM NADPH
0.28
2-[4-(dimethylamino)phenylazo]benzoic acid
GST-fusion protein, pH 8.0, 40°C
0.42
2-[4-(dimethylamino)phenylazo]benzoic acid
native protein, pH 8.0, 40°C
0.0986
balsalazide
wild type enzyme, using NADPH as cosubstrate, in 20 mM Tris–HCl pH 8.0, temperature not specified in the publication
0.1029
balsalazide
mutant enzyme Y131F, using NADPH as cosubstrate, in 20 mM Tris–HCl pH 8.0, temperature not specified in the publication
0.055
balsalzide
-
isoform AzoR2, pH 8.0, temperature not specified in the publication
0.34
balsalzide
-
isoform AzoR3, pH 8.0, temperature not specified in the publication
2.447
balsalzide
-
isoform AzoR1, pH 8.0, temperature not specified in the publication
0.00476
Methyl red
recombinant chimeric fusion protein AZR-GDH, pH 7.0, 40°C
0.0445
Methyl red
mutant enzyme Y131F, using NADPH as cosubstrate, in 20 mM Tris–HCl pH 8.0, temperature not specified in the publication
0.0927
Methyl red
wild type enzyme, using NADPH as cosubstrate, in 20 mM Tris–HCl pH 8.0, temperature not specified in the publication
0.26
Methyl red
-
isoform AzoR1, pH 8.0, temperature not specified in the publication
0.3
Methyl red
-
isoform AzoR2, pH 8.0, temperature not specified in the publication
0.983
Methyl red
-
isoform AzoR3, pH 8.0, temperature not specified in the publication
0.0081
NADH
-
pH not specified in the publication, temperature not specified in the publication
0.298
NADH
-
isoform AzoR1, pH 8.0, temperature not specified in the publication
0.525
NADH
-
isoform AzoR1, pH 8.0, temperature not specified in the publication
0.538
NADH
wild type enzyme, using methyl red as cosubstrate, in 20 mM Tris–HCl pH 8.0, temperature not specified in the publication
0.965
NADH
mutant enzyme Y131F, using methyl red as cosubstrate, in 20 mM Tris–HCl pH 8.0, temperature not specified in the publication
0.074
NADPH
-
in 25 mM potassium phosphate buffer (pH 7.1), 0.25 mM azo dye and 0.1 mM NADPH
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