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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-
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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 30C
0.018
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with (R)-1-(4-chlorophenyl)ethylamine as substrate, wild type enzyme, at pH 6.5 and 30C
0.08
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with N-methylcyclohexanamine as substrate, wild type enzyme, at pH 6.5 and 30C
0.084
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with (R)-1-(4-fluorophenyl)ethanamine as substrate, wild type enzyme, at pH 6.5 and 30C
0.11
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with 4-methylbenzylamine as substrate, wild type enzyme, at pH 6.5 and 30C
0.27
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with (S)-1-p-tolylethanamine as substrate, wild type enzyme, at pH 6.5 and 30C
0.33
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with cyclopentylamine as substrate, wild type enzyme, at pH 6.5 and 30C
0.34
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with benzylamine as substrate, wild type enzyme, at pH 6.5 and 30C
0.68
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with 2-amino-4-phenylbutane as substrate, wild type enzyme, at pH 6.5 and 30C
0.97
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with 2-aminocyclohexanol as substrate, wild type enzyme, at pH 6.5 and 30C
1.033
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with cyclooctanamine as substrate, wild type enzyme, at pH 6.5 and 30C
1.13
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with 2-aminopentane as substrate, wild type enzyme, at pH 6.5 and 30C
1.2
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with 2-aminoheptane as substrate, wild type enzyme, at pH 6.5 and 30C
1.49
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with 2-aminonorbornane hydrochloride as substrate, wild type enzyme, at pH 6.5 and 30C
1.66
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with (S)-1-phenylpropropan-1-amine as substrate, wild type enzyme, at pH 6.5 and 30C
2.35
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with (S)-1-aminoindan as substrate, wild type enzyme, at pH 6.5 and 30C
2.36
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with 1-phenylethanamine as substrate, wild type enzyme, at pH 6.5 and 30C
2.62
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with (S)-1-(4-chlorophenyl)ethylamine as substrate, wild type enzyme, at pH 6.5 and 30C
2.79
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with (S)-2-aminohexane as substrate, wild type enzyme, at pH 6.5 and 30C
3.058
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with 2-methylcyclohexanamine as substrate, wild type enzyme, at pH 6.5 and 30C
3.37
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with 1-(4-fluorophenyl)ethanamine as substrate, wild type enzyme, at pH 6.5 and 30C
3.51
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with (S)-(-)-1-phenylethylamine as substrate, wild type enzyme, at pH 6.5 and 30C
3.6
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with 2-amino-5-methylhexane as substrate, wild type enzyme, at pH 6.5 and 30C
4.56
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with (S)-1-(4-fluorophenyl)ethanamine as substrate, wild type enzyme, at pH 6.5 and 30C
5.6
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with cyclohexylamine as substrate, wild type enzyme, at pH 6.5 and 30C
5.69
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with (S)-1-aminotetraline as substrate, wild type enzyme, at pH 6.5 and 30C
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 6.09.0 at 4C 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 40C for at least 30 min, but decreases rapidly above 40C
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