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Information on EC 1.4.9.2 - aralkylamine dehydrogenase (azurin)
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1.4.9.2 aralkylamine dehydrogenase (azurin)IUBMB Comments
Phenazine methosulfate can act as acceptor. Acts on aromatic amines and, more slowly, on some long-chain aliphatic amines, but not on methylamine or ethylamine
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Word Map
- 1.4.9.2
- methylamine
- ttq
- tryptophylquinone
-
quinoproteins
-
tunnel
-
deamination
- tryptamine
-
half-reaction
-
ttq-dependent
-
alcaligenes
- benzylamines
- faecalis
-
breakage
-
h-transfer
- phenylethylamines
-
deflated
-
structure-reactivity
-
iminoquinone
-
enzyme-catalysed
- amicyanin
-
semi-classical
-
interprotein
The enzyme appears in viruses and cellular organisms
Synonyms
aromatic amine dehydrogenase, tyramine dehydrogenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
AADH
AMDH
aromatic amine dehydrogenase
dehydrogenase, arylamine
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-
-
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EC 1.4.99.4
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-
formerly
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quinohemoprotein amine dehydrogenase
tyramine dehydrogenase
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-
-
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AADH
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-
-
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aromatic amine dehydrogenase
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-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ArCH2NH2 + H2O + 2 azurin = ArCHO + NH3 + 2 reduced azurin
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-
-
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ArCH2NH2 + H2O + 2 azurin = ArCHO + NH3 + 2 reduced azurin
ping-pong mechanism
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ArCH2NH2 + H2O + 2 azurin = ArCHO + NH3 + 2 reduced azurin
breakage of the substrate C-H bond occurs via quantum mechanical tunneling. In steady-state reactions with benzylamine, breakage of C-H bond is only partially rate-limiting
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ArCH2NH2 + H2O + 2 azurin = ArCHO + NH3 + 2 reduced azurin
mechanism. In presence of substrate a covalent N-semiquinone substrate adduct is observed. Tryptophan tryptophylquinone redox state influences interprotein electron transfer
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ArCH2NH2 + H2O + 2 azurin = ArCHO + NH3 + 2 reduced azurin
proton transfer occurs predominantly to oxygen O2 of D128 in beta subunit in a reaction dominated by tunneling over 0.6 Angstroms. Tunneling is promoted by a short-range motion modulating proton-acceptor distance and no long-range coupled motion is required
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ArCH2NH2 + H2O + 2 azurin = ArCHO + NH3 + 2 reduced azurin
ping-pong mechanism
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
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redox reaction
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-
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reduction
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-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
aralkylamaralkylamine:azurin oxidoreductase (deaminating)
Phenazine methosulfate can act as acceptor. Acts on aromatic amines and, more slowly, on some long-chain aliphatic amines, but not on methylamine or ethylamine
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CAS REGISTRY NUMBER
COMMENTARY
85030-73-5
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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
1,3-diaminopropane + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
1,6-diaminohexane + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
2-phenylethylamine + H2O + 2,6-dichlorophenolindophenol
phenylacetaldehyde + NH3 + reduced 2,6-dichlorophenolindophenol
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-
-
-
r
beta-phenylethylamine + acceptor + H2O
? + NH3 + reduced acceptor
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-
-
?
beta-phenylethylamine + H2O + 2,6-dichlorophenol indophenol
phenylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
beta-phenylethylamine + H2O + 2,6-dichlorophenolindophenol
phenylacetaldehyde + NH3 + reduced 2,6-dichlorophenolindophenol
butylamine + H2O + 2,6-dichlorophenol indophenol
butanal + NH3 + reduced 2,6-dichlorophenol indophenol
cadaverine + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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-
-
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?
dopamine + H2O + 2,6-dichlorophenol indophenol
(3,4-dihydroxyphenyl)acetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
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-
-
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?
hexylamine + H2O + 2,6-dichlorophenol indophenol
hexanal + NH3 + reduced 2,6-dichlorophenol indophenol
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-
-
-
?
histamine + H2O + 2,6-dichlorophenol indophenol
1H-imidazol-4-ylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
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high activity at substrate concentration 1 mM
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-
?
pentylamine + H2O + 2,6-dichlorophenol indophenol
pentanal + NH3 + reduced 2,6-dichlorophenol indophenol
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-
-
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?
phenazine ethosulfate + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
phenazine methosulfate + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
propylamine + H2O + 2,6-dichlorophenol indophenol
propanal + NH3 + reduced 2,6-dichlorophenol indophenol
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low activity
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-
?
putrescine + H2O + 2,6-dichlorophenol indophenol
4-aminobutanal + NH3 + reduced 2,6-dichlorophenol indophenol
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-
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?
serotonin + H2O + 2,6-dichlorophenol indophenol
6-hydroxy-4H-indol-3-yl-acetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
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-
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?
spermidine + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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low activity
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-
?
spermine + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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low activity
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?
tryptamine + H2O + 2,6-dichlorophenol indophenol
4H-indol-3-yl-acetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
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-
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?
tyramine + H2O + 2,6-dichlorophenol indophenol
4-hydroxyphenylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
1,3-diaminopropane + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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-
-
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?
1,3-diaminopropane + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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-
-
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?
1,6-diaminohexane + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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-
-
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?
1,6-diaminohexane + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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-
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?
ArCH2NH2 + H2O + 2 azurin
ArCHO + NH3 + 2 reduced azurin
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azurin markedly facilitates electron transfer from the enzyme to each cytochrome tested. AADH and azurin may form an electron transfer complex with a c-type cytochrome
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-
?
ArCH2NH2 + H2O + 2 azurin
ArCHO + NH3 + 2 reduced azurin
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?
aromatic amines + acceptor + H2O
? + reduced acceptor + NH3
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physiological acceptor: azurin, not amicyanin
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-
?
aromatic amines + acceptor + H2O
? + reduced acceptor + NH3
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specific for phenylethylamines, but also reacts to a lesser extent with primary aliphatic amines
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?
aromatic amines + acceptor + H2O
? + reduced acceptor + NH3
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physiological acceptor: azurin, not amicyanin
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?
aromatic amines + acceptor + H2O
? + reduced acceptor + NH3
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specific for phenylethylamines, but also reacts to a lesser extent with primary aliphatic amines
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?
aromatic amines + acceptor + H2O
? + reduced acceptor + NH3
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catabolism
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?
benzylamine + acceptor + H2O
benzaldehyde + NH3 + reduced acceptor
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?
benzylamine + acceptor + H2O
benzaldehyde + NH3 + reduced acceptor
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?
benzylamine + H2O + 2,6-dichlorophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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?
benzylamine + H2O + 2,6-dichlorophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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analysis of limiting rate constants
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?
benzylamine + H2O + 2,6-dichlorophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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?
beta-phenylethylamine + H2O + 2,6-dichlorophenol indophenol
phenylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
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?
beta-phenylethylamine + H2O + 2,6-dichlorophenol indophenol
phenylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
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?
beta-phenylethylamine + H2O + 2,6-dichlorophenolindophenol
phenylacetaldehyde + NH3 + reduced 2,6-dichlorophenolindophenol
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?
beta-phenylethylamine + H2O + 2,6-dichlorophenolindophenol
phenylacetaldehyde + NH3 + reduced 2,6-dichlorophenolindophenol
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?
butylamine + H2O + 2,6-dichlorophenol indophenol
butanal + NH3 + reduced 2,6-dichlorophenol indophenol
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?
butylamine + H2O + 2,6-dichlorophenol indophenol
butanal + NH3 + reduced 2,6-dichlorophenol indophenol
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?
dopamine + acceptor + H2O
4-(2-oxoethyl)-1,2-benzenediol + NH3 + reduced acceptor
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-
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?
dopamine + acceptor + H2O
4-(2-oxoethyl)-1,2-benzenediol + NH3 + reduced acceptor
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?
dopamine + acceptor + H2O
4-(2-oxoethyl)-1,2-benzenediol + NH3 + reduced acceptor
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?
methylamine + acceptor + H2O
formaldehyde + NH3 + reduced acceptor
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?
methylamine + acceptor + H2O
formaldehyde + NH3 + reduced acceptor
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?
n-amylamine + H2O + 2 blue protein
? + NH3 + 2 blue protein
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-
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?
n-amylamine + H2O + 2 blue protein
? + NH3 + 2 blue protein
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-
-
?
n-butylamine + H2O + 2 blue protein
butanal + NH3 + 2 blue protein
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?
n-butylamine + H2O + 2 blue protein
butanal + NH3 + 2 blue protein
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?
phenazine ethosulfate + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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-
-
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?
phenazine ethosulfate + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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-
-
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?
phenazine methosulfate + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
-
-
-
-
?
phenazine methosulfate + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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-
-
-
?
phenazine methosulfate + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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-
-
-
?
phenazine methosulfate + H2O + 2,6-dichlorophenol indophenol
? + NH3 + reduced 2,6-dichlorophenol indophenol
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-
-
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?
phenylethylamine + acceptor + H2O
phenylacetaldehyde + NH3 + reduced acceptor
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-
-
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?
phenylethylamine + acceptor + H2O
phenylacetaldehyde + NH3 + reduced acceptor
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-
-
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?
propylamine + H2O + 2 blue protein
propanal + NH3 + 2 blue protein
the azurin-like blue protein is reduced specifically during AMDH reaction. The amine oxidation system can be reconstituted using AMDH, blue protein, and the cytoplasmic membranes of the organism
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-
?
propylamine + H2O + 2 blue protein
propanal + NH3 + 2 blue protein
the azurin-like blue protein is reduced specifically during AMDH reaction. The amine oxidation system can be reconstituted using AMDH, blue protein, and the cytoplasmic membranes of the organism
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-
?
serotonin + acceptor + H2O
3-(2-oxoethyl)-1H-indol-5-ol + NH3 + reduced acceptor
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-
-
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?
serotonin + acceptor + H2O
3-(2-oxoethyl)-1H-indol-5-ol + NH3 + reduced acceptor
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-
-
-
?
serotonin + acceptor + H2O
3-(2-oxoethyl)-1H-indol-5-ol + NH3 + reduced acceptor
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-
-
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?
tryptamine + acceptor + H2O
1H-indole-3-acetaldehyde + NH3 + reduced acceptor
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-
-
-
?
tryptamine + acceptor + H2O
1H-indole-3-acetaldehyde + NH3 + reduced acceptor
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-
-
-
?
tryptamine + acceptor + H2O
1H-indole-3-acetaldehyde + NH3 + reduced acceptor
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-
-
-
?
tyramine + acceptor + H2O
4-hydroxyphenylacetaldehyde + NH3 + reduced acceptor
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-
-
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?
tyramine + acceptor + H2O
4-hydroxyphenylacetaldehyde + NH3 + reduced acceptor
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electron acceptor: azurin
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-
?
tyramine + acceptor + H2O
4-hydroxyphenylacetaldehyde + NH3 + reduced acceptor
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electron acceptor: phenazine methosulfate or phenazine ethosulfate
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-
?
tyramine + acceptor + H2O
4-hydroxyphenylacetaldehyde + NH3 + reduced acceptor
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-
-
-
?
tyramine + acceptor + H2O
4-hydroxyphenylacetaldehyde + NH3 + reduced acceptor
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electron acceptor: phenazine methosulfate or phenazine ethosulfate
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-
?
tyramine + acceptor + H2O
4-hydroxyphenylacetaldehyde + NH3 + reduced acceptor
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electron acceptor: azurin
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-
?
tyramine + acceptor + H2O
4-hydroxyphenylacetaldehyde + NH3 + reduced acceptor
-
-
-
-
?
tyramine + acceptor + H2O
4-hydroxyphenylacetaldehyde + NH3 + reduced acceptor
-
-
-
-
?
tyramine + H2O + 2,6-dichlorophenol indophenol
4-hydroxyphenylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
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best substrate
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-
?
tyramine + H2O + 2,6-dichlorophenol indophenol
4-hydroxyphenylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
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-
-
-
?
tyramine + H2O + 2,6-dichlorophenol indophenol
4-hydroxyphenylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
-
-
-
-
?
additional information
?
-
-
substrate specificity, overview, no activity with methylamine, dimethylamine, and trimethylamine
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-
?
additional information
?
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-
substrate specificity, overview, no activity with methylamine, dimethylamine, and trimethylamine
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-
?
additional information
?
-
-
para-substituted benzylamines like 4-methylbenzylamine, 4-nitrobenzylamine, 4-methoxybenzylamine, 4-fluorobenzylamine, 4-chlorobenzylamine, and 4-bromobenzylamine are poor reactivity probes for AADH
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-
?
additional information
?
-
-
slow reaction with aromatic amines
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-
?
additional information
?
-
-
para-substituted benzylamines like 4-methylbenzylamine, 4-nitrobenzylamine, 4-methoxybenzylamine, 4-fluorobenzylamine, 4-chlorobenzylamine, and 4-bromobenzylamine are poor reactivity probes for AADH
-
-
?
additional information
?
-
-
long-chain aliphatic amines, phenazine methosulfate is the only effective electron acceptor
-
-
?
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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
beta-phenylethylamine + H2O + 2,6-dichlorophenol indophenol
phenylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
aromatic amines + acceptor + H2O
? + reduced acceptor + NH3
-
physiological acceptor: azurin, not amicyanin
-
-
?
aromatic amines + acceptor + H2O
? + reduced acceptor + NH3
-
physiological acceptor: azurin, not amicyanin
-
-
?
aromatic amines + acceptor + H2O
? + reduced acceptor + NH3
-
catabolism
-
-
?
beta-phenylethylamine + H2O + 2,6-dichlorophenol indophenol
phenylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
-
-
-
-
?
beta-phenylethylamine + H2O + 2,6-dichlorophenol indophenol
phenylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
-
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
heme c
two mol of heme per mole of AMDH, 60 kDa subunit carries heme c. Typical absorption stectrum shows maxima at 554, 522, 420, and 320 nm in the reduced state and one peak at 410 nm, a shoulder at 350 nm, and a braod hill at 530 nm in the oxidized form
tryptophan tryptophylquinone
-
two molecules per enzyme, tryptophan tryptophylquinone reduction is about 80 times more rapid with tryptamine compared to beta-phenylethylamine
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
beta-phenylethylamine
-
substrate inhibition at higher concentrations
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
-
analysis of limiting rate constants of reaction with benzylamine and deuterated benzylamine at different pH values
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
9.11
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5.5 - 9.5
-
5.5: about 25% of activity maximum, 9.5: about 10% of activity maximum
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE