1.4.3.12: cyclohexylamine oxidase
This is an abbreviated version!
For detailed information about cyclohexylamine oxidase, go to the full flat file.
Word Map on EC 1.4.3.12
-
1.4.3.12
-
brevibacterium
-
deracemization
-
oxydans
-
monoamine
-
alicyclic
-
cyclohexanone
-
biocatalytic
-
deamination
-
flavin
-
monooxygenase
-
stereoselective
-
cage
-
flavoprotein
-
enantiomeric
-
dextromethorphan
-
fad
-
prosthetic
-
racemic
-
oxidases
-
chaas
-
synthesis
- 1.4.3.12
- brevibacterium
-
deracemization
- oxydans
-
monoamine
-
alicyclic
- cyclohexanone
-
biocatalytic
-
deamination
- flavin
- monooxygenase
-
stereoselective
-
cage
- flavoprotein
-
enantiomeric
- dextromethorphan
- fad
-
prosthetic
-
racemic
- oxidases
-
chaas
- synthesis
Reaction
Synonyms
ArCHAO, CF596_10820, chaA, CHAO, CHAOCCH12-C2
ECTree
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Substrates Products
Substrates Products on EC 1.4.3.12 - cyclohexylamine oxidase
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REACTION DIAGRAM
(1R)-1-(4-chlorophenyl)ethan-1-amine + H2O + O2
1-(4-chlorophenyl)ethanone + NH3 + H2O2
-
-
-
-
?
(1R)-1-phenylethan-1-amine + H2O + O2
1-phenylacetaldehyde + NH3 + H2O2
-
-
-
-
?
(1R,2R)-2-aminocyclohexanol + O2 + H2O
cyclohexanone + NH3 + H2O2
Arthrobacter sp. TYUT010-15
the enzyme shows highly R-selective deamination activity toward beta-amino alcohols
-
-
?
(1R,2R)-2-aminocyclopentanol + O2 + H2O
cyclopentanone + NH3 + H2O2
Arthrobacter sp. TYUT010-15
the enzyme shows highly R-selective deamination activity toward beta-amino alcohols
-
-
?
(1R,2S)-1-amino-2-indanol + O2 + H2O
? + NH3 + H2O2
Arthrobacter sp. TYUT010-15
the enzyme shows highly R-selective deamination activity toward beta-amino alcohols
-
-
?
(1S)-1-(4-chlorophenyl)ethan-1-amine + H2O + O2
1-(4-chlorophenyl)ethanone + NH3 + H2O2
-
-
-
-
?
(1S)-1-phenylethan-1-amine + H2O + O2
1-phenylacetaldehyde + NH3 + H2O2
-
-
-
-
?
(1S)-1-phenylpropan-1-amine + H2O + O2
1-phenylpropan-1-one + NH3 + H2O2
-
-
-
-
?
(1S,2R)-1-amino-2-indanol + O2 + H2O
? + NH3 + H2O2
Arthrobacter sp. TYUT010-15
the enzyme shows highly R-selective deamination activity toward beta-amino alcohols
-
-
?
(1S,2S)-2-aminocyclohexanol + O2 + H2O
cyclohexanone + NH3 + H2O2
Arthrobacter sp. TYUT010-15
the enzyme shows highly R-selective deamination activity toward beta-amino alcohols
-
-
?
(1S,2S)-2-aminocyclopentanol + O2 + H2O
cyclopentanone + NH3 + H2O2
Arthrobacter sp. TYUT010-15
the enzyme shows highly R-selective deamination activity toward beta-amino alcohols
-
-
?
(R)-1-(4-chlorophenyl)ethylamine + O2 + H2O
1-(4-chlorophenyl)ethanone + NH3 + H2O2
-
-
-
-
?
(R)-1-(4-fluorophenyl)ethanamine + O2 + H2O
1-(4-fluorophenyl)ethanone + NH3 + H2O2
-
-
-
-
?
(S)-1-(4-chlorophenyl)ethylamine + O2 + H2O
1-(4-chlorophenyl)ethanone + NH3 + H2O2
-
-
-
-
?
(S)-1-(4-fluorophenyl)ethanamine + O2 + H2O
1-(4-fluorophenyl)ethanone + NH3 + H2O2
-
-
-
-
?
(S)-1-p-tolylethanamine + O2 + H2O
1-(4-methylphenyl)ethanone + NH3 + H2O2
-
-
-
-
?
(S)-1-phenylpropan-1-amine + O2 + H2O
1-phenylpropionaldehyde + NH3 + H2O2
-
-
-
-
?
(S)-2-heptylamine + O2 + H2O
heptan-2-one + NH3 + H2O2
-
25% activity compared to cyclohexylamine
-
-
?
(S)-alpha-methylbenzylamine + O2 + H2O
?
-
55% activity compared to cyclohexylamine
-
-
?
1,2,3,4-tetrahydro-2-naphthylamine + O2 + H2O
? + NH3 + H2O2
-
23% of the activity compared to cyclohexylamine
-
?
1,2-cyclohexanediamine + O2 + H2O
cyclohexaneamine + NH3 + H2O2
-
18% of the activity compared to cyclohexylamine
-
?
1-(4-chlorophenyl)ethanamine + O2 + H2O
?
-
35% activity compared to cyclohexylamine
-
-
?
1-(4-fluorophenyl)ethanamine + O2 + H2O
1-(4-fluorophenyl)ethanone + NH3 + H2O2
-
-
-
-
?
1-(4-fluorophenyl)ethanamine + O2 + H2O
?
-
61% activity compared to cyclohexylamine
-
-
?
1-(4-methylphenyl)ethanamine + O2 + H2O
?
-
5% activity compared to cyclohexylamine
-
-
?
1-(4-methylphenyl)methanamine + O2 + H2O
?
-
1% activity compared to cyclohexylamine
-
-
?
1-(naphthalen-1-yl)ethanamine + O2 + H2O
?
-
1% activity compared to cyclohexylamine
-
-
?
1-indanamine + O2 + H2O
1-indanone + NH3 + H2O2
-
27% activity compared to cyclohexylamine
-
-
?
1-phenylethanamine + O2 + H2O
1-phenylacetaldehyde + NH3 + H2O2
-
-
-
-
?
1-phenylethanamine + O2 + H2O
1-phenylethanone + NH3 + H2O2
-
48% activity compared to cyclohexylamine
-
-
?
2-amino-4-phenylbutane + O2 + H2O
4-phenylbutan-2-one + NH3 + H2O2
-
-
-
-
?
2-amino-5-methylhexane + O2 + H2O
5-methylhexane-2-one + NH3 + H2O2
-
-
-
-
?
2-ethyl-1-hexylamine + O2 + H2O
2-ethylhexanaldehyde + NH3 + H2O2
-
-
-
-
?
2-heptylamine + O2 + H2O
heptan-2-one + NH3 + H2O2
-
24% activity compared to cyclohexylamine
-
-
?
2-methyl-1,2,3,4-tetrahydroquinoline + O2 + H2O
(R)-2-methyl-1,2,3,4-tetrahydroquinoline + NH3 + H2O2
2-methylcyclohexanamine + O2 + H2O
?
-
56% activity compared to cyclohexylamine
-
-
?
2-methylpropan-1-amine + O2 + H2O
?
-
0.1% activity compared to cyclohexylamine
-
-
?
4-methylbenzylamine + O2 + H2O
4-methylbenzaldehyde + NH3 + H2O2
-
-
-
-
?
4-methylcyclohexanamine + O2 + H2O
4-methylcyclohexanone + NH3 + H2O2
-
41% of the activity with cyclohexylamine
-
-
?
4-methylcyclohexylamine + O2 + H2O
?
-
133% activity compared to cyclohexylamine
-
-
?
4-methylpiperidine + O2 + H2O
?
-
0.1% activity compared to cyclohexylamine
-
-
?
4-phenylbutan-2-amine + O2 + H2O
?
-
12% activity compared to cyclohexylamine
-
-
?
5-methylhexan-2-amine + O2 + H2O
?
-
9% activity compared to cyclohexylamine
-
-
?
6-amino-2-methylheptan-2-ol + O2 + H2O
?
-
0.1% activity compared to cyclohexylamine
-
-
?
bicyclo[2.2.1]heptan-2-amine + O2 + H2O
?
-
2% activity compared to cyclohexylamine
-
-
?
butan-2-amine + O2 + H2O
?
-
3% activity compared to cyclohexylamine
-
-
?
cycloheptanamine + O2 + H2O
?
-
75% activity compared to cyclohexylamine
-
-
?
cyclooctanamine + O2 + H2O
?
-
23% activity compared to cyclohexylamine
-
-
?
hexan-1-amine + O2 + H2O
?
-
1% activity compared to cyclohexylamine
-
-
?
trans-2-aminocyclohexanol + O2 + H2O
?
-
16% activity compared to cyclohexylamine
-
-
?
heptan-2-one + NH3 + H2O2
-
0.1% activity compared to cyclohexylamine
-
-
?
(R)-2-heptylamine + O2 + H2O
heptan-2-one + NH3 + H2O2
-
0.1% activity compared to cyclohexylamine
-
-
?
?
-
the enzyme is able to completely deracemize 100 mM 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline under Turner's deracemization conditions to afford (S)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline in 80% isolated yield and 99% nantiomeric excess at a semipreparative scale (0.4 mmol)
-
-
?
1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline + + O2 + H2O
?
-
the enzyme is able to completely deracemize 100 mM 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline under Turner's deracemization conditions to afford (S)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline in 80% isolated yield and 99% nantiomeric excess at a semipreparative scale (0.4 mmol)
-
-
?
(R)-2-methyl-1,2,3,4-tetrahydroquinoline + NH3 + H2O2
-
-
-
-
?
2-methyl-1,2,3,4-tetrahydroquinoline + O2 + H2O
(R)-2-methyl-1,2,3,4-tetrahydroquinoline + NH3 + H2O2
-
-
-
-
?
2-methylcyclohexanone + NH3 + H2O2
-
22% of the activity with cyclohexylamine
-
-
?
2-methylcyclohexanamine + O2 + H2O
2-methylcyclohexanone + NH3 + H2O2
-
-
-
-
?
? + NH3 + H2O2
-
7% activity compared to cyclohexylamine
-
-
?
3-phenylpropan-1-amine + H2O + O2
? + NH3 + H2O2
-
7% activity compared to cyclohexylamine
-
-
?
cycloheptanone + NH3 + H2O2
-
55% of the activity with cyclohexylamine
-
-
?
cycloheptylamine + O2 + H2O
cycloheptanone + NH3 + H2O2
-
42% of the activity compared to cyclohexylamine
-
?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
-
-
-
-
?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
-
best substrate
-
-
?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
-
highly specific for alicyclic monoamines and aliphatic monoamines
-
?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
-
100% activity
-
-
?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
-
-
-
-
?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
-
best substrate
-
-
?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
-
100% activity
-
-
?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
-
-
-
-
?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
-
-
-
?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
-
highly specific for alicyclic monoamines and aliphatic monoamines
-
?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
-
-
-
?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
-
-
-
-
?
cyclohexylamine + O2 + H2O
cyclohexanone + NH3 + H2O2
-
highly specific for alicyclic primary amines, oxygen is the only electron acceptor
-
?
cyclopentanone + NH3 + H2O2
-
7% of the activity with cyclohexylamine
-
-
?
cyclopentylamine + O2 + H2O
cyclopentanone + NH3 + H2O2
-
best substrate
-
-
?
cyclopentylamine + O2 + H2O
cyclopentanone + NH3 + H2O2
-
highly specific for alicyclic monoamines and aliphatic monoamines
-
?
cyclopentylamine + O2 + H2O
cyclopentanone + NH3 + H2O2
-
highly specific for alicyclic monoamines and aliphatic monoamines
-
?
D-valine ethyl ester
-
isomerization reaction
-
-
?
L-valine ethyl ester
D-valine ethyl ester
-
isomerization reaction
-
-
?
N-methylcyclohexanamine + O2 + H2O
?
-
6% activity compared to cyclohexylamine
-
-
?
cyclohexanone + methylamine + H2O2
-
highly specific for alicyclic monoamines and aliphatic monoamines
-
?
N-methylcyclohexylamine + O2 + H2O
cyclohexanone + methylamine + H2O2
-
highly specific for alicyclic monoamines and aliphatic monoamines
-
?
L-phenylalanine ethyl ester
-
deracemization reaction
-
-
?
racemic phenylalanine ethyl ester
L-phenylalanine ethyl ester
-
deracemization reaction
-
-
?
D-valine ethyl ester
-
deracemization reaction
-
-
?
racemic valine ethyl ester
D-valine ethyl ester
-
deracemization reaction
-
-
?
butanone + NH3 + H2O2
-
highly specific for alicyclic monoamines and aliphatic monoamines
-
?
secondary butylamine + O2 + H2O
butanone + NH3 + H2O2
-
highly specific for alicyclic monoamines and aliphatic monoamines
-
?
?
-
-
deracemization of 1-aminotetraline by coupling wild type enzyme with a nonselective reducing agent NH3·BH3 is a route to norsertraline
-
-
?
additional information
?
-
-
no activity with (R)-alpha-methylbenzylamine, 2-methylpiperidine and tetrahydroquinaldine
-
-
?
additional information
?
-
-
trace activity with (R)-2-aminohexane, 1-hexylamine, (R)-(-)-1-phenylethylamine, (R)-1-p-tolylethanamine, (R)-1-aminoindan, (S)-(-)-Nalpha-dimethylbenzylamine, 2-methylpiperidine, 4-methylpiperidine, 2-methyl-1,2,3,4-tetrahydroquinoline, and N,N-dimethylcyclohexylamine. No activity with 1-naphthalen-1-ylethanamine
-
-
?
additional information
?
-
-
when cyclohexylamine oxidase in combination with a borane-ammonia complex as reducing agent is applied to the deracemization of several substrates, excellent enantiomeric ratios (higher than 99:1) and good isolated yields (62-75%) of the corresponding (R)-amines are obtained
-
-
?
additional information
?
-
-
no activitiy towards (R)-N-(prop-2-yn-1-yl)-2, 3-dihydro-1H-inden-1-amine, 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, (S)-N-methyl-1-phenylethanamine, and 1-methyl-1,2,3,4-tetrahydroisoquinoline
-
-
?
additional information
?
-
-
deracemization of 1-aminotetraline by coupling wild type enzyme with a nonselective reducing agent NH3·BH3 is a route to norsertraline
-
-
?
additional information
?
-
-
trace activity with (R)-2-aminohexane, 1-hexylamine, (R)-(-)-1-phenylethylamine, (R)-1-p-tolylethanamine, (R)-1-aminoindan, (S)-(-)-Nalpha-dimethylbenzylamine, 2-methylpiperidine, 4-methylpiperidine, 2-methyl-1,2,3,4-tetrahydroquinoline, and N,N-dimethylcyclohexylamine. No activity with 1-naphthalen-1-ylethanamine
-
-
?
additional information
?
-
-
no activity with (R)-alpha-methylbenzylamine, 2-methylpiperidine and tetrahydroquinaldine
-
-
?
additional information
?
-
-
when cyclohexylamine oxidase in combination with a borane-ammonia complex as reducing agent is applied to the deracemization of several substrates, excellent enantiomeric ratios (higher than 99:1) and good isolated yields (62-75%) of the corresponding (R)-amines are obtained
-
-
?