Information on EC 1.4.3.12 - cyclohexylamine oxidase

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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
1.4.3.12
-
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RECOMMENDED NAME
GeneOntology No.
cyclohexylamine oxidase
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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
-
-
-
-
oxidative deamination
-
-
-
-
redox reaction
-
-
-
-
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.
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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
(1R)-1-(4-chlorophenyl)ethan-1-amine + H2O + O2
1-(4-chlorophenyl)ethanone + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
(1R)-1-phenylethan-1-amine + H2O + O2
1-phenylacetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
(1S)-1-(4-chlorophenyl)ethan-1-amine + H2O + O2
1-(4-chlorophenyl)ethanone + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
(1S)-1-phenylethan-1-amine + H2O + O2
1-phenylacetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
(1S)-1-phenylpropan-1-amine + H2O + O2
1-phenylpropan-1-one + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
(2R)-heptan-2-amine + H2O + O2
heptan-2-one + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
(2S)-heptan-2-amine + H2O + O2
heptan-2-one + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
(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
-
-
-
-
?
(S)-1-aminoindan + O2 + H2O
?
show the reaction diagram
-
-
-
-
?
(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-phenylethanamine + O2 + H2O
? + NH3 + H2O2
show the reaction diagram
(S)-1-phenylethylamine + O2 + H2O
?
show the reaction diagram
-
-
-
-
?
(S)-1-phenylpropan-1-amine + O2 + H2O
1-phenylpropionaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
(S)-2-aminohexane + O2 + H2O
hexan-2-one + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
(S)-2-heptylamine + O2 + H2O
heptan-2-one + NH3 + H2O2
show the reaction diagram
-
25% activity compared to cyclohexylamine
-
-
?
(S)-alpha-methylbenzylamine + O2 + H2O
?
show the reaction diagram
-
55% activity compared to cyclohexylamine
-
-
?
(S)-N-benzyl-1-phenylethylamine + O2 + H2O
?
show the reaction diagram
-
-
-
-
?
1,2,3,4-tetrahydro-2-naphthylamine + O2 + H2O
? + NH3 + H2O2
show the reaction diagram
-
23% of the activity compared to cyclohexylamine
-
?
1,2-cyclohexanediamine + O2 + H2O
cyclohexaneamine + NH3 + H2O2
show the reaction diagram
-
18% of the activity compared to cyclohexylamine
-
?
1-(4-chlorophenyl)ethanamine + O2 + H2O
?
show the reaction diagram
-
35% activity compared to cyclohexylamine
-
-
?
1-(4-fluorophenyl)ethanamine + O2 + H2O
1-(4-fluorophenyl)ethanone + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
1-(4-fluorophenyl)ethanamine + O2 + H2O
?
show the reaction diagram
-
61% activity compared to cyclohexylamine
-
-
?
1-(4-methylphenyl)ethanamine + O2 + H2O
?
show the reaction diagram
-
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
-
-
?
1-(naphthalen-1-yl)ethanamine + O2 + H2O
?
show the reaction diagram
-
1% activity compared to cyclohexylamine
-
-
?
1-indanamine + O2 + H2O
1-indanone + NH3 + H2O2
show the reaction diagram
-
27% activity compared to cyclohexylamine
-
-
?
1-phenylethanamine + O2 + H2O
1-phenylacetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
1-phenylethanamine + O2 + H2O
1-phenylethanone + NH3 + H2O2
show the reaction diagram
-
48% activity compared to cyclohexylamine
-
-
?
2-amino-4-phenylbutane + O2 + H2O
4-phenylbutan-2-one + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
2-amino-5-methylhexane + O2 + H2O
5-methylhexane-2-one + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
2-aminocyclohexanol + O2 + H2O
?
show the reaction diagram
-
-
-
-
?
2-aminoheptane + O2 + H2O
heptan-2-one + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
2-aminonorbornane + O2 + H2O
?
show the reaction diagram
-
-
-
-
?
2-aminopentane + O2 + H2O
pentan-2-one + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
2-ethyl-1-hexylamine + O2 + H2O
2-ethylhexanaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
2-heptylamine + O2 + H2O
heptan-2-one + NH3 + H2O2
show the reaction diagram
-
24% activity compared to cyclohexylamine
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-
?
2-methyl-1,2,3,4-tetrahydroquinoline + O2 + H2O
(R)-2-methyl-1,2,3,4-tetrahydroquinoline + NH3 + H2O2
show the reaction diagram
2-methylcyclohexanamine + O2 + H2O
2-methylcyclohexanone + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
2-methylcyclohexanamine + O2 + H2O
?
show the reaction diagram
-
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
-
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
-
0.1% activity compared to cyclohexylamine
-
-
?
benzylamine + O2 + H2O
benzaldehyde + NH3 + H2O2
show the reaction diagram
bicyclo[2.2.1]heptan-2-amine + O2 + H2O
?
show the reaction diagram
-
2% activity compared to cyclohexylamine
-
-
?
butan-2-amine + O2 + H2O
?
show the reaction diagram
-
3% activity compared to cyclohexylamine
-
-
?
cycloheptanamine + O2 + H2O
?
show the reaction diagram
-
75% activity compared to cyclohexylamine
-
-
?
cycloheptylamine + O2 + H2O
cycloheptanone + NH3 + H2O2
show the reaction diagram
-
42% of the activity compared to cyclohexylamine
-
?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
show the reaction diagram
cyclooctanamine + O2 + H2O
?
show the reaction diagram
-
23% activity compared to cyclohexylamine
-
-
?
cyclooctanamine + O2 + H2O
cyclooctanone + NH3 + H2O2
show the reaction diagram
-
-
-
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?
cyclopentylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
show the reaction diagram
-
best substrate
-
-
?
cyclopentylamine + O2 + H2O
cyclopentanone + NH3 + H2O2
show the reaction diagram
hexan-1-amine + O2 + H2O
?
show the reaction diagram
-
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
-
16% activity compared to cyclohexylamine
-
-
?
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
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Cd2+
-
38% inhibition at 10 mM
Cu2+
-
complete inhibition at 10 mM
Hg2+
-
complete inhibition at 10 mM
N-ethylmaleimide
-
27% inhibition at 0.05 mM
p-chloromercuribenzoate
-
91% inhibition at 0.0005 mM, partially reversed by glutathione
Quinacrine
Zn2+
-
48% inhibition at 10 mM
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.07 - 0.32
(S)-1-aminotetraline
0.56 - 1.03
(S)-1-phenylethanamine
-
0.27 - 1.12
2-methyl-1,2,3,4-tetrahydroquinoline
-
0.25 - 7.71
Cyclohexylamine
0.22 - 2.04
cyclooctanamine
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.96 - 10.62
(S)-1-aminotetraline
0.16 - 4.15
(S)-1-phenylethanamine
-
0.003 - 0.31
2-methyl-1,2,3,4-tetrahydroquinoline
-
4.77 - 16.33
Cyclohexylamine
3.03 - 7.68
cyclooctanamine
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
22.31 - 71.5
(S)-1-aminotetraline
0.19 - 7.42
(S)-1-phenylethanamine
-
0.003 - 1.15
2-methyl-1,2,3,4-tetrahydroquinoline
-
0.62 - 10.63
Cyclohexylamine
3.47 - 17.23
cyclooctanamine
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.013
-
with 2-ethyl-1-hexylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.018
-
with (R)-1-(4-chlorophenyl)ethylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.08
-
with N-methylcyclohexanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.084
-
with (R)-1-(4-fluorophenyl)ethanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.11
-
with 4-methylbenzylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.27
-
with (S)-1-p-tolylethanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.33
-
with cyclopentylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.34
-
with benzylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
0.68
-
with 2-amino-4-phenylbutane as substrate, wild type enzyme, at pH 6.5 and 30°C
0.97
-
with 2-aminocyclohexanol as substrate, wild type enzyme, at pH 6.5 and 30°C
1.033
-
with cyclooctanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
1.13
-
with 2-aminopentane as substrate, wild type enzyme, at pH 6.5 and 30°C
1.2
-
with 2-aminoheptane as substrate, wild type enzyme, at pH 6.5 and 30°C
1.49
-
with 2-aminonorbornane hydrochloride as substrate, wild type enzyme, at pH 6.5 and 30°C
1.66
-
with (S)-1-phenylpropropan-1-amine as substrate, wild type enzyme, at pH 6.5 and 30°C
2.35
-
with (S)-1-aminoindan as substrate, wild type enzyme, at pH 6.5 and 30°C
2.36
-
with 1-phenylethanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
2.62
-
with (S)-1-(4-chlorophenyl)ethylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
2.79
-
with (S)-2-aminohexane as substrate, wild type enzyme, at pH 6.5 and 30°C
3.058
-
with 2-methylcyclohexanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
3.37
-
with 1-(4-fluorophenyl)ethanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
3.51
-
with (S)-(-)-1-phenylethylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
3.6
-
with 2-amino-5-methylhexane as substrate, wild type enzyme, at pH 6.5 and 30°C
4.56
-
with (S)-1-(4-fluorophenyl)ethanamine as substrate, wild type enzyme, at pH 6.5 and 30°C
5.6
-
with cyclohexylamine as substrate, wild type enzyme, at pH 6.5 and 30°C
5.69
-
with (S)-1-aminotetraline as substrate, wild type enzyme, at pH 6.5 and 30°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
80000
-
gel filtration
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
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POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
flavoprotein
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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
M5AWH1
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 7
-
stable between
395988
6 - 9
-
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
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
stable up to
40
-
the wild type enzyme is stable at 40°C for at least 30 min, but decreases rapidly above 40°C
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DEAE cellulose DE-52 column chromatography, and Toyopearl Butyl-650S column chromatography
M5AWH1
DEAE column chromatography, and gel filtration
-
DEAE column chromatography, and Superdex 200 gel filtration
-
to homogeneity, chromatography steps
-
to homogeneity, fractionation and chromatography steps
-
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21 cells
-
expressed in Escherichia coli BL21(DE3) cells
-
expressed in Escherichia coli Top10 cells
-
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
L199A
-
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
L199F
-
the mutant is more active than the wild type enzyme toward the primary amines
L199I
-
the mutant is more active than the wild type enzyme toward the primary amines
L353M
-
the mutant shows 7-445% higher activity towards primary aliphatic amines with cycloalkane or aromatic moieties
M226F
-
the mutant shows reduced catalytic efficiency with (S)-1-phenylethanamine and increased catalytic efficiency with 2-methyl-1,2,3,4-tetrahydroquinoline compared to the wild type enzyme
M226I
-
the mutant is more active than the wild type enzyme toward the primary amines
M226T
-
the mutant is more active than the wild type enzyme toward the primary amines
T198A
-
the mutant exhibits enhanced activity relative to the wild type enzyme for most (S)-enantiomers of primary amines and some secondary amines
T198F/L199S
-
the mutant exhibits 240times higher catalytic efficiency with 2-methyl-1,2,3,4-tetrahydroquinoline than the wild type enzyme. The mutant shows reduced catalytic efficiency with (S)-1-phenylethanamine compared to the wild type enzyme
T198F/L199S/M226F
T198I
-
the mutant is more active than the wild type enzyme toward the primary amines
Y321I
-
the mutation enhances the enzyme activity toward the secondary amines and displays an enhanced catalytic efficiency toward 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline
Y321I/M226T
-
the double mutant acts on (S)-N-(prop-2-yn-1-yl)-2,3-dihydro-1H-inden-1-amine
Y321T
-
the mutation enhances the enzyme activity toward the secondary amines
Y459T
-
the mutant shows reduced catalytic efficiency with (S)-1-phenylethanamine and increased catalytic efficiency with 2-methyl-1,2,3,4-tetrahydroquinoline compared to the wild type enzyme
L199A
-
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
-
L199T
-
the mutant shows reduced catalytic efficiency with (S)-1-phenylethanamine and increased catalytic efficiency with 2-methyl-1,2,3,4-tetrahydroquinoline compared to the wild type enzyme
-
L353M
-
the mutant shows 7-445% higher activity towards primary aliphatic amines with cycloalkane or aromatic moieties
-
M226A
-
the mutant displays an enhanced activity (5-400%) towards most substrates
-
M226F
-
the mutant shows reduced catalytic efficiency with (S)-1-phenylethanamine and increased catalytic efficiency with 2-methyl-1,2,3,4-tetrahydroquinoline compared to the wild type enzyme
-
T198F
-
the mutant shows reduced catalytic efficiency with (S)-1-phenylethanamine and increased catalytic efficiency with 2-methyl-1,2,3,4-tetrahydroquinoline compared to the wild type enzyme
-
T198F/L199S
-
the mutant exhibits 240times higher catalytic efficiency with 2-methyl-1,2,3,4-tetrahydroquinoline than the wild type enzyme. The mutant shows reduced catalytic efficiency with (S)-1-phenylethanamine compared to the wild type enzyme
-
T198F/L199S/M226F
-
the mutant exhibits 406times higher catalytic efficiency with 2-methyl-1,2,3,4-tetrahydroquinoline than the wild type enzyme. The mutant shows reduced catalytic efficiency with (S)-1-phenylethanamine compared to the wild type enzyme
-
Y321A
-
the mutant shows higher catalytic efficiency towards cyclooctanamine compared to the wild type enzyme
-
Y321F
-
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
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LINKS TO OTHER DATABASES (specific for EC-Number 1.4.3.12)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)