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Information on EC 1.4.3.12 - cyclohexylamine oxidase
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1.4.3.12 cyclohexylamine oxidaseIUBMB Comments
A flavoprotein (FAD). Some other cyclic amines can act instead of cyclohexylamine, but not simple aliphatic and aromatic amides.
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Word Map
- 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
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
cyclohexylamine oxidase, chaocch12-c2, archao, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
chaA
CHAO
CHAOCCH12-C2
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cyclohexylamine + O2 + H2O = cyclohexanone + NH3 + H2O2
a flavoprotein, FAD
-
-
-
cyclohexylamine + O2 + H2O = cyclohexanone + NH3 + H2O2
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
LITERATURE
oxidation
-
-
-
-
oxidative deamination
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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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
63116-97-2
-
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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
(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
-
-
?
(R)-2-heptylamine + O2 + H2O
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
-
-
?
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)
-
-
?
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)
-
-
?
2-methyl-1,2,3,4-tetrahydroquinoline + O2 + H2O
(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-methylcyclohexanamine + O2 + H2O
2-methylcyclohexanone + NH3 + H2O2
-
22% of the activity with cyclohexylamine
-
-
?
2-methylcyclohexanamine + O2 + H2O
2-methylcyclohexanone + NH3 + H2O2
-
-
-
-
?
3-phenylpropan-1-amine + H2O + O2
? + NH3 + H2O2
-
7% activity compared to cyclohexylamine
-
-
?
3-phenylpropan-1-amine + H2O + O2
? + NH3 + H2O2
-
7% activity compared to cyclohexylamine
-
-
?
cycloheptylamine + O2 + H2O
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
-
?
cyclopentylamine + O2 + H2O
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
-
?
L-valine ethyl ester
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
-
-
?
N-methylcyclohexylamine + O2 + H2O
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
-
?
racemic phenylalanine ethyl ester
L-phenylalanine ethyl ester
-
deracemization reaction
-
-
?
racemic phenylalanine ethyl ester
L-phenylalanine ethyl ester
-
deracemization reaction
-
-
?
racemic valine ethyl ester
D-valine ethyl ester
-
deracemization reaction
-
-
?
racemic valine ethyl ester
D-valine ethyl ester
-
deracemization reaction
-
-
?
secondary butylamine + O2 + H2O
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
-
?
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
?
-
-
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
-
-
?
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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
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
-
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
-
?
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
-
?
N-methylcyclohexylamine + O2 + H2O
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
-
?
secondary butylamine + O2 + H2O
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
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
p-chloromercuribenzoate
-
91% inhibition at 0.0005 mM, partially reversed by glutathione
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.99
(S)-1-phenylethanamine
-
mutant enzyme T198F/L199S/M226F, at pH 6.5 and 30°C
1.03
(S)-1-phenylethanamine
-
mutant enzyme T198F/L199S, at pH 6.5 and 30°C
0.36
1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline
-
pH 7.5, 45°C, mutant enzyme P396A
-
0.52
1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline
-
pH 7.5, 45°C, mutant enzyme F327A
-
0.53
1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline
-
pH 7.5, 45°C, mutant enzyme G202A
-
0.61
1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline
-
pH 7.5, 45°C, mutant enzyme L200A
-
1.24
1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline
-
pH 7.5, 45°C, mutant enzyme T203A
-
1.84
1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline
-
pH 7.5, 45°C, mutant enzyme I201A
-
1.88
1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline
-
pH 7.5, 45°C, mutant enzyme L295I
-
2.13
1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline
-
pH 7.5, 45°C, mutant enzyme F317A
-
2.2
1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline
-
pH 7.5, 45°C, wild-type enzyme
-
2.71
1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline
-
pH 7.5, 45°C, mutant enzyme I173A
-
6.54
1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline
-
pH 7.5, 45°C, mutant enzy