Information on EC 3.5.1.101 - L-proline amide hydrolase

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The expected taxonomic range for this enzyme is: Pseudomonas azotoformans

EC NUMBER
COMMENTARY
3.5.1.101
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RECOMMENDED NAME
GeneOntology No.
L-proline amide hydrolase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)-piperidine-2-carboxamide + H2O = (S)-piperidine-2-carboxylic acid + NH3
show the reaction diagram
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L-prolinamide + H2O = L-proline + NH3
show the reaction diagram
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SYSTEMATIC NAME
IUBMB Comments
(S)-piperidine-2-carboxamide amidohydrolase
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SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
L-amino acid amidase
Q76KX0
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L-amino acid amidase
Pseudomonas azotoformans IAM 1603
Q76KX0
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LaaA
Pseudomonas azotoformans IAM 1603
Q76KX0
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S-stereoselective piperazine-2-tert-butylcarboxamide hydrolase
Q76KX0
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S-stereoselective piperazine-2-tert-butylcarboxamide hydrolase
Pseudomonas azotoformans IAM 1603
Q76KX0
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CAS REGISTRY NUMBER
COMMENTARY
79633-25-3
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Pseudomonas azotoformans IAM 1603
IAM 1603
SwissProt
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
(R,S)-piperazine-2-tert-butylcarboxamide + H2O
(S)-piperazine-2-tert-butylcarboxylic acid + NH3
show the reaction diagram
Pseudomonas azotoformans, Pseudomonas azotoformans IAM 1603
Q76KX0
% of the activity with L-proline amide
-
-
?
(S)-piperazine-2-carboxamide + H2O
(S)-piperazine-2-carboxylic acid + NH3
show the reaction diagram
Pseudomonas azotoformans, Pseudomonas azotoformans IAM 1603
Q76KX0
3.7% of the activity with L-proline amide
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-
?
(S)-piperazine-2-tert-butylcarboxamide + H2O
(S)-piperazine-2-carboxylic acid + tert-butylamine
show the reaction diagram
Q76KX0
0.2% of the activity with L-proline amide
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-
?
(S)-piperidine-2-carboxamide + H2O
(S)-piperidine-2-carboxylic acid + NH3
show the reaction diagram
Q76KX0
32% of the activity with L-proline amide
-
-
?
L-alanine amide + H2O
L-alanine + NH3
show the reaction diagram
Q76KX0
10.6% of the activity with L-proline amide
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-
?
L-isoleucine amide + H2O
L-isoleucine + NH3
show the reaction diagram
Q76KX0
0.17% of the activity with L-proline amide
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?
L-leucine amide + H2O
L-leucine + NH3
show the reaction diagram
Pseudomonas azotoformans, Pseudomonas azotoformans IAM 1603
Q76KX0
0.46% of the activity with L-proline amide
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?
L-methionine amide + H2O
L-methionine + NH3
show the reaction diagram
Q76KX0
4.2% of the activity with L-proline amide
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?
L-phenylalanine amide + H2O
L-phenylalanine + NH3
show the reaction diagram
Pseudomonas azotoformans, Pseudomonas azotoformans IAM 1603
Q76KX0
0.97% of the activity with L-proline amide
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?
L-proline amide + H2O
L-proline + NH3
show the reaction diagram
Q76KX0
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-
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?
L-proline-p-nitroanilide + H2O
? + NH3
show the reaction diagram
Q76KX0
40.9% of the activity with L-proline amide
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-
?
L-serine amide + H2O
L-serine + NH3
show the reaction diagram
Q76KX0
0.43% of the activity with L-proline amide
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-
?
L-threonine amide + H2O
L-threonine + NH3
show the reaction diagram
Q76KX0
0.12% of the activity with L-proline amide
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?
L-tryptophan amide + H2O
L-tryptophan + NH3
show the reaction diagram
Q76KX0
0.2% of the activity with L-proline amide
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?
L-tyrosine amide + H2O
L-tyrosine + NH3
show the reaction diagram
Q76KX0
0.086% of the activity with L-proline amide
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?
additional information
?
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Pseudomonas azotoformans, Pseudomonas azotoformans IAM 1603
Q76KX0
the following compounds are not substrates for the amidase: L-arginine amide, L-asparagine amide, L-isoasparagine, L-glutaminamide, L-isoglutamine, glycine amide, L-histidine amide, L-lysine amide, L-valine amide, D-proline amide, L-alanyl-L-alanine, L-alanylglycine, glycylglycine, L-prolyl-L-alanine and L-prolylglycine. LaaA can not act on the peptide substrates such as L-prolyl-L-alanine, L-prolylglycine, L-alanyl-L-alanine, L-alanylglycine and glycylglycine
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ag+
Q76KX0
1 mM, complete inhibition
Cd2+
Q76KX0
1 mM, complete inhibition
CoCl2
Q76KX0
1 mM, 52% inhibition
Hg2+
Q76KX0
1 mM, complete inhibition
iodoacetate
Q76KX0
1 mM, 40% inhibition
NEM
Q76KX0
1 mM, 24% inhibition
NiCl2
Q76KX0
1 mM, 70% inhibition
p-chloromercuribenzoate
Q76KX0
1 mM, 67% inhibition
PbCl2
Q76KX0
1 mM, 73% inhibition
phenylhydrazine
Q76KX0
1 mM, complete inhibition
Zn2+
Q76KX0
1 mM, complete inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.58
L-proline-p-nitroanilide
Q76KX0
30°C, pH 7.0
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.000894
Q76KX0
S-stereoselective amidase from Pseudomonas azotoformans IAM 1603
192
Q76KX0
LaaA from Escharichia coli JM109 harboring pSTB20
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
32000
Q76KX0
gel filtration
692156
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
Q76KX0
1 * 34000, SDS-PAGE
monomer
Pseudomonas azotoformans IAM 1603
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1 * 34000, SDS-PAGE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
45
Q76KX0
stable up to
692156
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, stored without loss of activity for more than six months in the buffer containing 50% glycerol
Q76KX0
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
Q76KX0
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
Q76KX0
Escherichia coli cells overexpressing the laaA gene have been demonstrated to be applicable to the S-stereoselective hydrolysis of (R,S)-piperazine-2-tert-butylcarboxamide to produce (S)-piperazine-2-carboxylic acid with high optical purity. Enantiomerically pure piperazine-2-carboxylic acid and its tert-butylcarboxamide derivative are important chiral building blocks for some pharmacologically active compounds such as N-methyl-D-aspartate antagonist for glutamate receptor, cardioprotective nucleoside transport blocker and HIV protease inhibitor
synthesis
Pseudomonas azotoformans IAM 1603
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Escherichia coli cells overexpressing the laaA gene have been demonstrated to be applicable to the S-stereoselective hydrolysis of (R,S)-piperazine-2-tert-butylcarboxamide to produce (S)-piperazine-2-carboxylic acid with high optical purity. Enantiomerically pure piperazine-2-carboxylic acid and its tert-butylcarboxamide derivative are important chiral building blocks for some pharmacologically active compounds such as N-methyl-D-aspartate antagonist for glutamate receptor, cardioprotective nucleoside transport blocker and HIV protease inhibitor
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