Information on EC 3.5.1.85 - (S)-N-acetyl-1-phenylethylamine hydrolase

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The expected taxonomic range for this enzyme is: Rhodococcus equi

EC NUMBER
COMMENTARY
3.5.1.85
-
RECOMMENDED NAME
GeneOntology No.
(S)-N-acetyl-1-phenylethylamine hydrolase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
N-acetylphenylethylamine + H2O = phenylethylamine + acetate
show the reaction diagram
induction of (S)-N-acetyl-1-phenylethylamine hydrolase
Rhodococcus hoagii
-
N-acetylphenylethylamine + H2O = phenylethylamine + acetate
show the reaction diagram
induction of (S)-N-acetyl-1-phenylethylamine hydrolase
Rhodococcus hoagii Ac6
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of linear amides
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
(S)-N-acetylphenylethylamine:H2O hydrolase
Inhibited by phenylmethanesulfonyl fluoride. Some related acetylated compounds are hydrolysed with variable enantiomeric selectivities.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
(S)-N-acetyl-1-phenylethylamine amidohydrolase
-
-
-
-
(S)-specific acylase
-
-
-
-
(S)-specific N-acetyl-1-phenylethylamine amidohydrolase
-
-
-
-
hydrolase, (S)-N-acetyl-1-phenylethylamine
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-
-
-
CAS REGISTRY NUMBER
COMMENTARY
192230-94-7
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Rhodococcus hoagii
strain Ac6, DSMZ no. 10278
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-
Manually annotated by BRENDA team
Rhodococcus hoagii Ac6
strain Ac6, DSMZ no. 10278
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-N-acetyl-1-phenylethylamine + H2O
(S)-1-phenylethylamine + acetate
show the reaction diagram
Rhodococcus hoagii
-
high enantioselectivity, enantioselectivity of enzyme is 350 for (S)-N-acetyl-1-phenylethylamine, substrate and inducer of enzyme
enantiomerically pure (S)-1-phenylethylamine
?
(S)-N-acetyl-1-phenylethylamine + H2O
(S)-1-phenylethylamine + acetate
show the reaction diagram
Rhodococcus hoagii Ac6
-
high enantioselectivity, enantioselectivity of enzyme is 350 for (S)-N-acetyl-1-phenylethylamine, substrate and inducer of enzyme
enantiomerically pure (S)-1-phenylethylamine
?
additional information
?
-
Rhodococcus hoagii
-
enzyme is highly enantioselective, some related N-acetylated compounds are hydrolysed with variable enantiomeric selectivities, substrate specificity and enantioselectivity
-
-
-
additional information
?
-
Rhodococcus hoagii Ac6
-
enzyme is highly enantioselective, some related N-acetylated compounds are hydrolysed with variable enantiomeric selectivities, substrate specificity and enantioselectivity
-
-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
Rhodococcus hoagii
-
metal cations not required
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ba2+
Rhodococcus hoagii
-
1 mM: 5% inhibition
Ca2+
Rhodococcus hoagii
-
1 mM: 10% inhibition
Cd2+
Rhodococcus hoagii
-
1 mM: 15% inhibition
Co2+
Rhodococcus hoagii
-
1 mM: 31% inhibition
Cu2+
Rhodococcus hoagii
-
1 mM: 12% inhibition
Mg2+
Rhodococcus hoagii
-
1 mM: 10% inhibition
Ni2+
Rhodococcus hoagii
-
1 mM: 60% inhibition
Pb2+
Rhodococcus hoagii
-
1 mM: 5% inhibition
phenylmethylsulfonyl fluoride
Rhodococcus hoagii
-
strong inhibition, 0.1 mM: 95% inhibition, 0.01 mM: 84% inhibition
V3+
Rhodococcus hoagii
-
1 mM: 11% inhibition
Zn2+
Rhodococcus hoagii
-
1 mM: 32% inhibition
Mn2+
Rhodococcus hoagii
-
1 mM: 13% inhibition
additional information
Rhodococcus hoagii
-
no inhibition by 10 mM chelating agents: EDTA, citrate and 10 mM thiol-reducing agents: dithiothreitol, mercaptoethanol, reduced glutathione; no inhibition by 1 mM Fe3+
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(S)-N-acetyl-1-phenylethylamine
Rhodococcus hoagii
-
activation and induction, addition of more than 3 g/l (S)-N-acetyl-1-phenylethylamine to medium affects growth and acylase production negatively
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.6
(S)-N-acetyl-1-phenylethylamine
Rhodococcus hoagii
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.87
Rhodococcus hoagii
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5 - 7
Rhodococcus hoagii
-
broad pH optimum
7
Rhodococcus hoagii
-
assay at
additional information
Rhodococcus hoagii
-
pI at pH 3.5
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5.5 - 9
Rhodococcus hoagii
-
activity between
6 - 8.5
Rhodococcus hoagii
-
broad activity optimum between, activity lost rather quickly below pH 6.0 and above pH 8.5 with the decay being steeper on the acidic side of optimum curve
additional information
Rhodococcus hoagii
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-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
Rhodococcus hoagii
-
assay at
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
94000
Rhodococcus hoagii
-
gel filtration
209241
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
Rhodococcus hoagii
-
2 * 50000, two identical subunits, SDS-PAGE
dimer
Rhodococcus hoagii Ac6
-
2 * 50000, two identical subunits, SDS-PAGE
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6 - 8.5
Rhodococcus hoagii
-
stable between, activity lost rather quickly below pH 6.0 and above pH 8.5 with the decay being steeper on the acidic side of optimum curve
209241
7
Rhodococcus hoagii
-
at pH 7.0, 30°C, half-life of around 350 days
209241
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
Rhodococcus hoagii
-
at 30°C, pH 7.0, half-life of around 350 days. 30°C for 34 days: 94% of activity retained
209241
44
Rhodococcus hoagii
-
half-life: 10 min
209241
additional information
Rhodococcus hoagii
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-
209241
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
-
Rhodococcus hoagii
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
Rhodococcus hoagii
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economic synthesis of enantiomerically pure (S)-1-phenylethylamine. Enantiomerically pure chiral amines, (S)-enantiomer of 1-phenylethylamine is an example of such compound of high interest, a field of high interest for pharmaceutical industry
synthesis
Rhodococcus hoagii Ac6
-
economic synthesis of enantiomerically pure (S)-1-phenylethylamine. Enantiomerically pure chiral amines, (S)-enantiomer of 1-phenylethylamine is an example of such compound of high interest, a field of high interest for pharmaceutical industry
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