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Information on EC 1.7.1.17 - FMN-dependent NADH-azoreductase
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1.7.1.17 FMN-dependent NADH-azoreductaseIUBMB Comments
Requires FMN. The enzyme catalyses the reductive cleavage of an azo bond in aromatic azo compounds to form the corresponding amines. Does not accept NADPH. cf. EC 1.7.1.6, azobenzene reductase.
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The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
fmn-dependent nadh-azoreductase, indigo reductase, azoro, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
AZO
azo-dye reductase
AzoA
AzoR
AzoR1
azoreductase
AzoRo
AzrA
flavin-containing oxygen-insensitive azoreductase
FMN dependent azoreductase
FMN-dependent NADH-azoreductase
FMN-dependent-NADH azoreductase
indigo reductase
NADH-azoreductase
AzoR
-
-
ambiguous
-
NADH-azoreductase
-
-
ambiguous
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
anthranilate + N,N-dimethyl-1,4-phenylenediamine + 2 NAD+ = 2-(4-dimethylaminophenyl)diazenylbenzoate + 2 NADH + 2 H+
anthranilate + N,N-dimethyl-1,4-phenylenediamine + 2 NAD+ = 2-(4-dimethylaminophenyl)diazenylbenzoate + 2 NADH + 2 H+
-
-
-
-
anthranilate + N,N-dimethyl-1,4-phenylenediamine + 2 NAD+ = 2-(4-dimethylaminophenyl)diazenylbenzoate + 2 NADH + 2 H+
ping-pong reaction mechanism
anthranilate + N,N-dimethyl-1,4-phenylenediamine + 2 NAD+ = 2-(4-dimethylaminophenyl)diazenylbenzoate + 2 NADH + 2 H+
ping-pong reaction mechanism, overview
anthranilate + N,N-dimethyl-1,4-phenylenediamine + 2 NAD+ = 2-(4-dimethylaminophenyl)diazenylbenzoate + 2 NADH + 2 H+
ping-pong reaction mechanism. Enzymatic reaction involves an electron transfer from nicotinamide dinucleotide (NADH) to flavin mononucleotide (FMN) (ping) followed by a transfer from FMNH2 to the substrate (pong), key role of flavin
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SYSTEMATIC NAME
IUBMB Comments
N,N-dimethyl-1,4-phenylenediamine, anthranilate:NAD+ oxidoreductase
Requires FMN. The enzyme catalyses the reductive cleavage of an azo bond in aromatic azo compounds to form the corresponding amines. Does not accept NADPH. cf. EC 1.7.1.6, azobenzene reductase.
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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-pyridylazo)-2-naphthol + 2 NADH + 2 H+
pyridin-2-amine + 1-aminonaphthalen-2-ol + 2 NAD+
-
-
-
?
2-(4-dimethylaminophenyl)diazenylbenzoate + 2 NADH + 2 H+
anthranilate + N,N-dimethyl-1,4-phenylenediamine + 2 NAD+
2-(4-dimethylaminophenylazo) benzoic acid + NADH + H+
N,N'-dimethyl-p-phenylenediamine + 2-aminobenzoic acid + NAD+
4'-(diethylamino)-azobenzene-2-carboxylic acid + 2 NADH + 2 H+
2-aminobenzoic acid + N,N-diethyl-p-phenylenediamine + 2 NAD+
i.e. ethyl red
-
-
?
4'-(dimethylamino)-azobenzene-2-carboxylic acid + 2 NADH + 2 H+
2-aminobenzoic acid + N,N-dimethyl-p-phenylenediamine + 2 NAD+
4'-(dimethylamino)-azobenzene-2-carboxylic acid + 2 NADPH + 2 H+
2-aminobenzoic acid + N,N-dimethyl-p-phenylenediamine + 2 NADP+
4-(dimethylamino)azobenzene + NADH + H+
N,N-dimethyl-1,4-phenylenediamine + aniline + NAD+
7-nitrocoumarin-3-carboxylic acid + 2 NADH + 2 H+
7-aminocoumarin-3-carboxylic acid + NAD+ + H2O
via 7-nitrosocoumarin-3-carboxylic acid and 7-hydroxylaminocoumarin-3-carboxylic acid intermediates
-
-
?
7-nitrocoumarin-3-carboxylic acid + NADH + H+
7-aminocoumarin-3-carboxylic acid + NAD+ + H2O
-
-
-
?
acid red 88 + 2 NADH + 2 H+
4-aminobenzene-1-sulfonic acid + 1-aminonaphthalen-2-ol + 2 NAD+
amaranth + 2 NADH + 2 H+
4-aminonaphthalene-1-sulfonic acid + 4-amino-3-hydroxynaphthalene-2,7-disulfonic acid + 2 NAD+
amaranth + 2 NADPH + 2 H+
4-aminonaphthalene-1-sulfonic acid + 4-amino-3-hydroxynaphthalene-2,7-disulfonic acid + 2 NADP+
-
-
-
-
?
anthranilate + N,N-dimethyl-1,4-phenylenediamine + 2 NAD+
2-(4-dimethylaminophenyl)diazenylbenzoate + 2 NADH + 2 H+
-
-
-
-
?
ethyl red + 2 NADH + 2 H+
anthranilate + N,N-diethyl-1,4-phenylenediamine + 2 NAD+
-
-
-
?
fast red E + 2 NADH + 2 H+
4-aminonaphthalene-1-sulfonic acid + 5-amino-6-hydroxynaphthalene-2-sulfonic acid + 2 NAD+
-
-
-
-
?
fast red E + 2 NADPH + 2 H+
4-aminonaphthalene-1-sulfonic acid + 5-amino-6-hydroxynaphthalene-2-sulfonic acid + 2 NADP+
-
-
-
-
?
Methyl Red + NADH + H+
2-aminobenzoic acid + N,N-dimethyl-1,4-phenylenediamine + NAD+
-
-
-
?
orange G + 2 NADH + 2 H+
aniline + 8-amino-7-hydroxynaphthalene-1,3-disulfonic acid + 2 NAD+
-
-
-
-
?
orange G + 2 NADPH + 2 H+
aniline + 8-amino-7-hydroxynaphthalene-1,3-disulfonic acid + 2 NADP+
orange II + 2 NADPH + 2 H+
4-aminobenzene-1-sulfonic acid + 1-aminonaphthalen-2-ol + 2 NADP+ + 2 NAD+
Reactive black 5 + 2 NADH + 2 H+
n-hydroxy-benzenamine + dimethyl phthalate + phenylethyl alcohol + 4-methylphenol + 3-(methylthio)propanoic acid methyl ester + 2 NAD+
-
-
-
-
?
Reactive Orange + NADH + H+
?
-
substrate for immobilized enzyme (catalyst meso-cellular foam-A) only
-
-
?
2-(4-dimethylaminophenyl)diazenylbenzoate + 2 NADH + 2 H+
anthranilate + N,N-dimethyl-1,4-phenylenediamine + 2 NAD+
i.e. azo dye methyl red
-
-
?
2-(4-dimethylaminophenyl)diazenylbenzoate + 2 NADH + 2 H+
anthranilate + N,N-dimethyl-1,4-phenylenediamine + 2 NAD+
i.e. azo dye methyl red, via a diazene intermediate
-
-
?
2-(4-dimethylaminophenylazo) benzoic acid + NADH + H+
N,N'-dimethyl-p-phenylenediamine + 2-aminobenzoic acid + NAD+
i.e. methyl red
-
-
?
2-(4-dimethylaminophenylazo) benzoic acid + NADH + H+
N,N'-dimethyl-p-phenylenediamine + 2-aminobenzoic acid + NAD+
i.e. methyl red
-
-
?
4'-(dimethylamino)-azobenzene-2-carboxylic acid + 2 NADH + 2 H+
2-aminobenzoic acid + N,N-dimethyl-p-phenylenediamine + 2 NAD+
i.e. methyl red
-
-
?
4'-(dimethylamino)-azobenzene-2-carboxylic acid + 2 NADH + 2 H+
2-aminobenzoic acid + N,N-dimethyl-p-phenylenediamine + 2 NAD+
-
i.e. methyl red
-
-
?
4'-(dimethylamino)-azobenzene-2-carboxylic acid + 2 NADH + 2 H+
2-aminobenzoic acid + N,N-dimethyl-p-phenylenediamine + 2 NAD+
i.e. methyl red
-
-
?
4'-(dimethylamino)-azobenzene-2-carboxylic acid + 2 NADH + 2 H+
2-aminobenzoic acid + N,N-dimethyl-p-phenylenediamine + 2 NAD+
-
i.e. methyl red
-
-
?
4'-(dimethylamino)-azobenzene-2-carboxylic acid + 2 NADH + 2 H+
2-aminobenzoic acid + N,N-dimethyl-p-phenylenediamine + 2 NAD+
i.e. methyl red
-
-
?
4'-(dimethylamino)-azobenzene-2-carboxylic acid + 2 NADH + 2 H+
2-aminobenzoic acid + N,N-dimethyl-p-phenylenediamine + 2 NAD+
i.e. methyl red
-
-
?
4'-(dimethylamino)-azobenzene-2-carboxylic acid + 2 NADH + 2 H+
2-aminobenzoic acid + N,N-dimethyl-p-phenylenediamine + 2 NAD+
i.e. methyl red
-
-
?
4'-(dimethylamino)-azobenzene-2-carboxylic acid + 2 NADPH + 2 H+
2-aminobenzoic acid + N,N-dimethyl-p-phenylenediamine + 2 NADP+
-
i.e. methyl red
-
-
?
4'-(dimethylamino)-azobenzene-2-carboxylic acid + 2 NADPH + 2 H+
2-aminobenzoic acid + N,N-dimethyl-p-phenylenediamine + 2 NADP+
i.e. methyl red
-
-
?
4'-(dimethylamino)-azobenzene-2-carboxylic acid + 2 NADPH + 2 H+
2-aminobenzoic acid + N,N-dimethyl-p-phenylenediamine + 2 NADP+
i.e. methyl red
-
-
?
4'-(dimethylamino)-azobenzene-2-carboxylic acid + 2 NADPH + 2 H+
2-aminobenzoic acid + N,N-dimethyl-p-phenylenediamine + 2 NADP+
-
i.e. methyl red
-
-
?
4-(dimethylamino)azobenzene + NADH + H+
N,N-dimethyl-1,4-phenylenediamine + aniline + NAD+
-
-
-
?
4-(dimethylamino)azobenzene + NADH + H+
N,N-dimethyl-1,4-phenylenediamine + aniline + NAD+
i.e. methyl yellow
-
-
?
4-(dimethylamino)azobenzene + NADH + H+
N,N-dimethyl-1,4-phenylenediamine + aniline + NAD+
-
-
-
?
4-(dimethylamino)azobenzene + NADH + H+
N,N-dimethyl-1,4-phenylenediamine + aniline + NAD+
i.e. methyl yellow
-
-
?
acid red 88 + 2 NADH + 2 H+
4-aminobenzene-1-sulfonic acid + 1-aminonaphthalen-2-ol + 2 NAD+
-
-
-
?
acid red 88 + 2 NADH + 2 H+
4-aminobenzene-1-sulfonic acid + 1-aminonaphthalen-2-ol + 2 NAD+
-
-
-
?
Allura Red + NADH + H+
?
-
substrate for immobilized enzyme (catalyst meso-cellular foam-A) only
-
-
?
Allura Red + NADH + H+
?
-
substrate for immobilized enzyme (catalyst meso-cellular foam-A) only
-
-
?
amaranth + 2 NADH + 2 H+
4-aminonaphthalene-1-sulfonic acid + 4-amino-3-hydroxynaphthalene-2,7-disulfonic acid + 2 NAD+
-
-
-
-
?
amaranth + 2 NADH + 2 H+
4-aminonaphthalene-1-sulfonic acid + 4-amino-3-hydroxynaphthalene-2,7-disulfonic acid + 2 NAD+
-
-
-
?
amaranth + 2 NADH + 2 H+
4-aminonaphthalene-1-sulfonic acid + 4-amino-3-hydroxynaphthalene-2,7-disulfonic acid + 2 NAD+
-
-
-
?
amaranth + 2 NADH + 2 H+
4-aminonaphthalene-1-sulfonic acid + 4-amino-3-hydroxynaphthalene-2,7-disulfonic acid + 2 NAD+
-
-
-
-
?
amaranth + 2 NADH + 2 H+
4-aminonaphthalene-1-sulfonic acid + 4-amino-3-hydroxynaphthalene-2,7-disulfonic acid + 2 NAD+
-
-
-
-
?
amaranth + 2 NADH + 2 H+
4-aminonaphthalene-1-sulfonic acid + 4-amino-3-hydroxynaphthalene-2,7-disulfonic acid + 2 NAD+
-
-
-
?
amaranth + 2 NADH + 2 H+
4-aminonaphthalene-1-sulfonic acid + 4-amino-3-hydroxynaphthalene-2,7-disulfonic acid + 2 NAD+
-
-
-
?
amaranth + 2 NADH + 2 H+
4-aminonaphthalene-1-sulfonic acid + 4-amino-3-hydroxynaphthalene-2,7-disulfonic acid + 2 NAD+
-
-
-
-
?
amaranth + 2 NADH + 2 H+
4-aminonaphthalene-1-sulfonic acid + 4-amino-3-hydroxynaphthalene-2,7-disulfonic acid + 2 NAD+
-
-
-
-
?
methyl orange + NADH + H+
?
-
substrate for immobilized enzyme (catalyst meso-cellular foam-A) only
-
-
?
methyl orange + NADH + H+
?
-
substrate for immobilized enzyme (catalyst meso-cellular foam-A) only
-
-
?
methyl red + NADH + H+
?
-
substrate for immobilized enzyme (catalyst meso-cellular foam-A) only
-
-
?
methyl red + NADH + H+
?
-
substrate for immobilized enzyme (catalyst meso-cellular foam-A) only
-
-
?
orange G + 2 NADPH + 2 H+
aniline + 8-amino-7-hydroxynaphthalene-1,3-disulfonic acid + 2 NADP+
-
-
-
?
orange G + 2 NADPH + 2 H+
aniline + 8-amino-7-hydroxynaphthalene-1,3-disulfonic acid + 2 NADP+
-
-
-
?
orange G + 2 NADPH + 2 H+
aniline + 8-amino-7-hydroxynaphthalene-1,3-disulfonic acid + 2 NADP+
-
-
-
-
?
orange I + 2 NADH + 2 H+
4-aminobenzene-1-sulfonic acid + 4-aminonaphthalen-1-ol + 2 NAD+
-
-
-
?
orange I + 2 NADH + 2 H+
4-aminobenzene-1-sulfonic acid + 4-aminonaphthalen-1-ol + 2 NAD+
-
-
-
?
orange II + 2 NADPH + 2 H+
4-aminobenzene-1-sulfonic acid + 1-aminonaphthalen-2-ol + 2 NADP+ + 2 NAD+
-
-
-
?
orange II + 2 NADPH + 2 H+
4-aminobenzene-1-sulfonic acid + 1-aminonaphthalen-2-ol + 2 NADP+ + 2 NAD+
-
-
-
?
additional information
?
-
the enzyme shows a negligible ability to use molecular oxygen as an electron acceptor
-
-
-
additional information
?
-
the enzyme shows a negligible ability to use molecular oxygen as an electron acceptor
-
-
-
additional information
?
-
active site structure analysis and substrate specificity, Azo compound binding structure, overview
-
-
?
additional information
?
-
AzoR utilizes NADH but not NADPH as an electron donor and binds FMN as a flavin cofactor
-
-
?
additional information
?
-
no activity with Ponceau SX. Recombinant AcpD reaction follows a ping-pong mechanism requiring 2 mol of NADH to reduce 1 mol of methyl red into 2-aminobenzoic acid and N,N'-dimethyl-p-phenylenediamine. On the other hand, the gene product cannot convert holo-acyl carrier protein into the apo form under either in vitro or in vivo conditions. These data indicate that the acpD gene product is not acyl carrier protein phosphodiesterase but an azoreductase
-
-
?
additional information
?
-
-
enzyme additionally acts as nitroreductase and selectively reduces the nitro group of 2-nitrophenol, 4-nitrobenzoic acid, 2-nitro-benzaldehyde and 3-nitrophenol
-
-
?
additional information
?
-
-
free enzyme has no activity with azobenzene, 4-phenylazophenol, Allura Red, Amido Black, Reactive Orange, Para Red, Chlorazol Black and Methyl Orange
-
-
-
additional information
?
-
-
free enzyme has no activity with azobenzene, 4-phenylazophenol, Allura Red, Amido Black, Reactive Orange, Para Red, Chlorazol Black and Methyl Orange
-
-
-
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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
2-(4-dimethylaminophenyl)diazenylbenzoate + 2 NADH + 2 H+
anthranilate + N,N-dimethyl-1,4-phenylenediamine + 2 NAD+
i.e. azo dye methyl red
-
-
?
4-(dimethylamino)azobenzene + NADH + H+
N,N-dimethyl-1,4-phenylenediamine + aniline + NAD+
7-nitrocoumarin-3-carboxylic acid + NADH + H+
7-aminocoumarin-3-carboxylic acid + NAD+ + H2O
-
-
-
?
anthranilate + N,N-dimethyl-1,4-phenylenediamine + 2 NAD+
2-(4-dimethylaminophenyl)diazenylbenzoate + 2 NADH + 2 H+
-
-
-
-
?
4-(dimethylamino)azobenzene + NADH + H+
N,N-dimethyl-1,4-phenylenediamine + aniline + NAD+
-
-
-
?
4-(dimethylamino)azobenzene + NADH + H+
N,N-dimethyl-1,4-phenylenediamine + aniline + NAD+
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
roseoflavin mononucleotide
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. With roseoflavin mononucleotide, the holoenzyme shiws about 30% of wild-type activity
FAD
60% of the activity with FMN. FAD is stably retained in the enzyme molecule without degradation to FMN
FMN
a flavin-containing enzyme the enzyme binds 1 FMN per subunit
FMN
FMN is tightly bound to the protein moiety, and this interaction is essential for the crystallization of AzoR
FMN
-
coexistence of at least three FMN-containing components in wild-type AzoR, i.e. FMN emitting at 490 nm, 530 nm and 600 nm, respectively
FMN
residues Trp105, Asn106, Leu107, Gly150, Gly151, Tyr153, Asn121 and Tyr129 are involved in binding the FMN isoalloxazine ring. Residue Trp105 is involved in FMN stabilization and destabilization
FMN
-
adding FMN as cofactor significantly improves the azodye-reducing activity of the cytosolic extract
FMN
-
adding FMN as cofactor significantly improves the azodye-reducing activity of the cytosolic extract
FMN
-
adding FMN as cofactor significantly improves the azodye-reducing activity of the cytosolic extract
FMN
FMN is present in the enzyme as a coenzyme and is not covalently bound to the enzyme
NADH
reaction with NADH is 13fold faster than with NADPH
NADPH
reaction with NADH is 13fold faster than with NADPH
additional information
AzoR utilizes NADH but not NADPH as an electron donor and binds FMN as a flavin cofactor
-
additional information
no cofactor: 8-amino-8-demethyl-riboflavin mononucleotide
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Fe2+