Information on EC 1.4.3.12 - cyclohexylamine oxidase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.4.3.12
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RECOMMENDED NAME
GeneOntology No.
cyclohexylamine oxidase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
cyclohexylamine + O2 + H2O = cyclohexanone + NH3 + H2O2
show the reaction diagram
a flavoprotein, FAD; A flavoprotein, FAD. Some other cyclic amines can act instead of cyclohexylamine, but not simple aliphatic and aromatic amides
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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oxidative deamination
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Caprolactam degradation
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
cyclohexylamine:oxygen oxidoreductase (deaminating)
A flavoprotein (FAD). Some other cyclic amines can act instead of cyclohexylamine, but not simple aliphatic and aromatic amides.
CAS REGISTRY NUMBER
COMMENTARY hide
63116-97-2
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-1-(4-chlorophenyl)ethylamine + O2 + H2O
1-(4-chlorophenyl)ethanone + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
(R)-1-(4-fluorophenyl)ethanamine + O2 + H2O
1-(4-fluorophenyl)ethanone + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
(R)-1-aminotetraline + O2 + H2O
?
show the reaction diagram
-
-
-
-
?
(R)-2-heptylamine + O2 + H2O
heptan-2-one + NH3 + H2O2
show the reaction diagram
(S)-1-(4-chlorophenyl)ethylamine + O2 + H2O
1-(4-chlorophenyl)ethanone + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
(S)-1-(4-fluorophenyl)ethanamine + O2 + H2O
1-(4-fluorophenyl)ethanone + NH3 + H2O2
show the reaction diagram
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?
(S)-1-aminoindan + O2 + H2O
?
show the reaction diagram
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-
-
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?
(S)-1-aminotetraline + O2 + H2O
?
show the reaction diagram
-
-
-
-
?
(S)-1-aminotetraline + O2 + H2O
tetralone + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
(S)-1-p-tolylethanamine + O2 + H2O
1-(4-methylphenyl)ethanone + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
(S)-1-phenylethylamine + O2 + H2O
?
show the reaction diagram
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-
-
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?
(S)-1-phenylpropan-1-amine + O2 + H2O
1-phenylpropionaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
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?
(S)-2-aminohexane + O2 + H2O
hexan-2-one + NH3 + H2O2
show the reaction diagram
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-
-
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?
(S)-2-heptylamine + O2 + H2O
heptan-2-one + NH3 + H2O2
show the reaction diagram
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25% activity compared to cyclohexylamine
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?
(S)-alpha-methylbenzylamine + O2 + H2O
?
show the reaction diagram
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55% activity compared to cyclohexylamine
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?
1,2,3,4-tetrahydro-2-naphthylamine + O2 + H2O
? + NH3 + H2O2
show the reaction diagram
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23% of the activity compared to cyclohexylamine
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?
1,2-cyclohexanediamine + O2 + H2O
cyclohexaneamine + NH3 + H2O2
show the reaction diagram
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18% of the activity compared to cyclohexylamine
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?
1-(4-chlorophenyl)ethanamine + O2 + H2O
?
show the reaction diagram
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35% activity compared to cyclohexylamine
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?
1-(4-fluorophenyl)ethanamine + O2 + H2O
1-(4-fluorophenyl)ethanone + NH3 + H2O2
show the reaction diagram
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?
1-(4-fluorophenyl)ethanamine + O2 + H2O
?
show the reaction diagram
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61% activity compared to cyclohexylamine
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?
1-(4-methylphenyl)ethanamine + O2 + H2O
?
show the reaction diagram
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5% activity compared to cyclohexylamine
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?
1-(4-methylphenyl)methanamine + O2 + H2O
?
show the reaction diagram
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1% activity compared to cyclohexylamine
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?
1-(naphthalen-1-yl)ethanamine + O2 + H2O
?
show the reaction diagram
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1% activity compared to cyclohexylamine
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?
1-indanamine + O2 + H2O
1-indanone + NH3 + H2O2
show the reaction diagram
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27% activity compared to cyclohexylamine
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?
1-phenylethanamine + O2 + H2O
1-phenylacetaldehyde + NH3 + H2O2
show the reaction diagram
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?
1-phenylethanamine + O2 + H2O
1-phenylethanone + NH3 + H2O2
show the reaction diagram
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48% activity compared to cyclohexylamine
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?
2-amino-4-phenylbutane + O2 + H2O
4-phenylbutan-2-one + NH3 + H2O2
show the reaction diagram
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?
2-amino-5-methylhexane + O2 + H2O
5-methylhexane-2-one + NH3 + H2O2
show the reaction diagram
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?
2-aminocyclohexanol + O2 + H2O
?
show the reaction diagram
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?
2-aminoheptane + O2 + H2O
heptan-2-one + NH3 + H2O2
show the reaction diagram
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?
2-aminonorbornane + O2 + H2O
?
show the reaction diagram
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?
2-aminopentane + O2 + H2O
pentan-2-one + NH3 + H2O2
show the reaction diagram
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?
2-ethyl-1-hexylamine + O2 + H2O
2-ethylhexanaldehyde + NH3 + H2O2
show the reaction diagram
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?
2-heptylamine + O2 + H2O
heptan-2-one + NH3 + H2O2
show the reaction diagram
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24% activity compared to cyclohexylamine
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?
2-methylcyclohexanamine + O2 + H2O
2-methylcyclohexanone + NH3 + H2O2
show the reaction diagram
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?
2-methylcyclohexanamine + O2 + H2O
?
show the reaction diagram
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56% activity compared to cyclohexylamine
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?
2-methylpropan-1-amine + O2 + H2O
?
show the reaction diagram
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0.1% activity compared to cyclohexylamine
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?
3-phenylpropan-1-amine + H2O + O2
? + NH3 + H2O2
show the reaction diagram
4-methylbenzylamine + O2 + H2O
4-methylbenzaldehyde + NH3 + H2O2
show the reaction diagram
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?
4-methylcyclohexylamine + O2 + H2O
?
show the reaction diagram
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133% activity compared to cyclohexylamine
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?
4-methylpiperidine + O2 + H2O
?
show the reaction diagram
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0.1% activity compared to cyclohexylamine
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?
4-phenylbutan-2-amine + O2 + H2O
?
show the reaction diagram
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12% activity compared to cyclohexylamine
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?
5-methylhexan-2-amine + O2 + H2O
?
show the reaction diagram
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9% activity compared to cyclohexylamine
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?
6-amino-2-methylheptan-2-ol + O2 + H2O
?
show the reaction diagram
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0.1% activity compared to cyclohexylamine
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?
benzylamine + O2 + H2O
benzaldehyde + NH3 + H2O2
show the reaction diagram
bicyclo[2.2.1]heptan-2-amine + O2 + H2O
?
show the reaction diagram
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2% activity compared to cyclohexylamine
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?
butan-2-amine + O2 + H2O
?
show the reaction diagram
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3% activity compared to cyclohexylamine
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?
cycloheptanamine + O2 + H2O
?
show the reaction diagram
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75% activity compared to cyclohexylamine
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?
cycloheptylamine + O2 + H2O
cycloheptanone + NH3 + H2O2
show the reaction diagram
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42% of the activity compared to cyclohexylamine
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?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
show the reaction diagram
cyclooctanamine + O2 + H2O
?
show the reaction diagram
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23% activity compared to cyclohexylamine
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?
cyclooctanamine + O2 + H2O
cyclooctanone + NH3 + H2O2
show the reaction diagram
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?
cyclopentylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
show the reaction diagram
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best substrate
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?
cyclopentylamine + O2 + H2O
cyclopentanone + NH3 + H2O2
show the reaction diagram
hexan-1-amine + O2 + H2O
?
show the reaction diagram
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1% activity compared to cyclohexylamine
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?
N-methylcyclohexanamine + O2 + H2O
?
show the reaction diagram
N-methylcyclohexylamine + O2 + H2O
cyclohexanone + methylamine + H2O2
show the reaction diagram
secondary butylamine + O2 + H2O
butanone + NH3 + H2O2
show the reaction diagram
trans-2-aminocyclohexanol + O2 + H2O
?
show the reaction diagram
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16% activity compared to cyclohexylamine
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
show the reaction diagram
cyclopentylamine + O2 + H2O
cyclopentanone + NH3 + H2O2
show the reaction diagram
N-methylcyclohexylamine + O2 + H2O
cyclohexanone + methylamine + H2O2
show the reaction diagram
secondary butylamine + O2 + H2O
butanone + NH3 + H2O2
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Cd2+
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38% inhibition at 10 mM
Cu2+
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complete inhibition at 10 mM
Hg2+
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complete inhibition at 10 mM
N-ethylmaleimide
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27% inhibition at 0.05 mM
p-chloromercuribenzoate
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91% inhibition at 0.0005 mM, partially reversed by glutathione
Quinacrine
Zn2+
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48% inhibition at 10 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.07 - 0.32
(S)-1-aminotetraline
0.25 - 7.71
Cyclohexylamine
0.22 - 2.04
cyclooctanamine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.96 - 10.62
(S)-1-aminotetraline
4.77 - 16.33
Cyclohexylamine
3.03 - 7.68
cyclooctanamine
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
22.31 - 71.5
(S)-1-aminotetraline
5448
0.62 - 10.63
Cyclohexylamine
1862
3.47 - 17.23
cyclooctanamine
5880
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.013
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with 2-ethyl-1-hexylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.018
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with (R)-1-(4-chlorophenyl)ethylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.08
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with N-methylcyclohexanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.084
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with (R)-1-(4-fluorophenyl)ethanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.11
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with 4-methylbenzylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.27
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with (S)-1-p-tolylethanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.33
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with cyclopentylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.34
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with benzylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.68
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with 2-amino-4-phenylbutane as substrate, wild type enzyme, at pH 6.5 and 30°C
0.97
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with 2-aminocyclohexanol as substrate, wild type enzyme, at pH 6.5 and 30°C
1.033
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with cyclooctanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
1.13
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with 2-aminopentane as substrate, wild type enzyme, at pH 6.5 and 30°C
1.2
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with 2-aminoheptane as substrate, wild type enzyme, at pH 6.5 and 30°C
1.49
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with 2-aminonorbornane hydrochloride as substrate, wild type enzyme, at pH 6.5 and 30°C
1.66
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with (S)-1-phenylpropropan-1-amine as substrate, wild type enzyme, at pH 6.5 and 30°C
2.35
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with (S)-1-aminoindan as substrate, wild type enzyme, at pH 6.5 and 30°C
2.36
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with 1-phenylethanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
2.62
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with (S)-1-(4-chlorophenyl)ethylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
2.79
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with (S)-2-aminohexane as substrate, wild type enzyme, at pH 6.5 and 30°C
3.058
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with 2-methylcyclohexanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
3.37
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with 1-(4-fluorophenyl)ethanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
3.51
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with (S)-(-)-1-phenylethylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
3.6
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with 2-amino-5-methylhexane as substrate, wild type enzyme, at pH 6.5 and 30°C
4.56
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with (S)-1-(4-fluorophenyl)ethanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
5.6
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with cyclohexylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
5.69
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with (S)-1-aminotetraline as substrate, wild type enzyme, at pH 6.5 and 30°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
80000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
flavoprotein
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method, using 30% (w/v) PEG 8000 and 0.2 M sodium acetate trihydrate in 0.1 M sodium cacodylate pH 6.5
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 7
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stable between
395988
6 - 9
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the enzyme retains more than 70% of its original activity over a broad range of pH 6.0–9.0 at 4°C for 24 h. However, stability decreases quickly in more acidic condition
724095
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
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stable up to
40
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the wild type enzyme is stable at 40°C for at least 30 min, but decreases rapidly above 40°C
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DEAE cellulose DE-52 column chromatography, and Toyopearl Butyl-650S column chromatography
DEAE column chromatography, and gel filtration
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to homogeneity, chromatography steps
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to homogeneity, fractionation and chromatography steps
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21 cells
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expressed in Escherichia coli BL21(DE3) cells
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
L199A
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the mutant shows generally lower activity (decrease of 15-97%) towards most substrates compared to wild type enzyme with the exception of the larger substrates, such as cyclooctanamine and bicyclic (S)-1-aminotetraline
L353M
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the mutant shows 7-445% higher activity towards primary aliphatic amines with cycloalkane or aromatic moieties
M226A
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the mutant displays an enhanced activity (5-400%) towards most substrates
Y321A
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the mutant shows higher catalytic efficiency towards cyclooctanamine compared to the wild type enzyme
Y321F
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the mutant shows higher catalytic efficiency towards cyclooctanamine compared to the wild type enzyme
L199A
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the mutant shows generally lower activity (decrease of 15-97%) towards most substrates compared to wild type enzyme with the exception of the larger substrates, such as cyclooctanamine and bicyclic (S)-1-aminotetraline
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L353M
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the mutant shows 7-445% higher activity towards primary aliphatic amines with cycloalkane or aromatic moieties
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M226A
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the mutant displays an enhanced activity (5-400%) towards most substrates
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Y321A
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the mutant shows higher catalytic efficiency towards cyclooctanamine compared to the wild type enzyme
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Y321F
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the mutant shows higher catalytic efficiency towards cyclooctanamine compared to the wild type enzyme
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis