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Information on EC 3.5.1.101 - L-proline amide hydrolase for references in articles please use BRENDA:EC3.5.1.101
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EC Tree
The enzyme appears in viruses and cellular organisms
Synonyms
L-amino acid amidase, LaaA, S-stereoselective piperazine-2-tert-butylcarboxamide hydrolase,
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S-stereoselective piperazine-2-tert-butylcarboxamide hydrolase
L-amino acid amidase
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LaaA
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S-stereoselective piperazine-2-tert-butylcarboxamide hydrolase
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S-stereoselective piperazine-2-tert-butylcarboxamide hydrolase
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(S)-piperidine-2-carboxamide + H2O = (S)-piperidine-2-carboxylate + NH3
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L-prolinamide + H2O = L-proline + NH3
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(S)-piperidine-2-carboxamide amidohydrolase
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(R,S)-piperazine-2-tert-butylcarboxamide + H2O
(S)-piperazine-2-tert-butylcarboxylic acid + NH3
(S)-piperazine-2-carboxamide + H2O
(S)-piperazine-2-carboxylic acid + NH3
(S)-piperazine-2-tert-butylcarboxamide + H2O
(S)-piperazine-2-carboxylic acid + tert-butylamine
0.2% of the activity with L-proline amide
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?
(S)-piperidine-2-carboxamide + H2O
(S)-piperidine-2-carboxylic acid + NH3
32% of the activity with L-proline amide
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?
L-alanine amide + H2O
L-alanine + NH3
10.6% of the activity with L-proline amide
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?
L-isoleucine amide + H2O
L-isoleucine + NH3
0.17% of the activity with L-proline amide
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?
L-leucine amide + H2O
L-leucine + NH3
L-methionine amide + H2O
L-methionine + NH3
4.2% of the activity with L-proline amide
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?
L-phenylalanine amide + H2O
L-phenylalanine + NH3
L-proline amide + H2O
L-proline + NH3
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?
L-proline-p-nitroanilide + H2O
? + NH3
40.9% of the activity with L-proline amide
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?
L-serine amide + H2O
L-serine + NH3
0.43% of the activity with L-proline amide
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?
L-threonine amide + H2O
L-threonine + NH3
0.12% of the activity with L-proline amide
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?
L-tryptophan amide + H2O
L-tryptophan + NH3
0.2% of the activity with L-proline amide
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?
L-tyrosine amide + H2O
L-tyrosine + NH3
0.086% of the activity with L-proline amide
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?
additional information
?
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(R,S)-piperazine-2-tert-butylcarboxamide + H2O
(S)-piperazine-2-tert-butylcarboxylic acid + NH3
% of the activity with L-proline amide
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?
(R,S)-piperazine-2-tert-butylcarboxamide + H2O
(S)-piperazine-2-tert-butylcarboxylic acid + NH3
% of the activity with L-proline amide
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?
(S)-piperazine-2-carboxamide + H2O
(S)-piperazine-2-carboxylic acid + NH3
3.7% of the activity with L-proline amide
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?
(S)-piperazine-2-carboxamide + H2O
(S)-piperazine-2-carboxylic acid + NH3
3.7% of the activity with L-proline amide
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?
L-leucine amide + H2O
L-leucine + NH3
0.46% of the activity with L-proline amide
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?
L-leucine amide + H2O
L-leucine + NH3
0.46% of the activity with L-proline amide
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?
L-phenylalanine amide + H2O
L-phenylalanine + NH3
0.97% of the activity with L-proline amide
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?
L-phenylalanine amide + H2O
L-phenylalanine + NH3
0.97% of the activity with L-proline amide
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?
additional information
?
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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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additional information
?
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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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Ag+
1 mM, complete inhibition
Cd2+
1 mM, complete inhibition
CoCl2
1 mM, 52% inhibition
Hg2+
1 mM, complete inhibition
iodoacetate
1 mM, 40% inhibition
NiCl2
1 mM, 70% inhibition
p-chloromercuribenzoate
1 mM, 67% inhibition
PbCl2
1 mM, 73% inhibition
phenylhydrazine
1 mM, complete inhibition
Zn2+
1 mM, complete inhibition
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0.58
L-proline-p-nitroanilide
30°C, pH 7.0
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0.000894
S-stereoselective amidase from Pseudomonas azotoformans IAM 1603
192
LaaA from Escharichia coli JM109 harboring pSTB20
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IAM 1603
SwissProt
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IAM 1603
SwissProt
brenda
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34000
1 * 34000, SDS-PAGE
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monomer
1 * 34000, SDS-PAGE
monomer
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1 * 34000, SDS-PAGE
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-20°C, stored without loss of activity for more than six months in the buffer containing 50% glycerol
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expression in Escherichia coli
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synthesis
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
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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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Komeda, H.; Harada, H.; Washika, S.; Sakamoto, T.; Ueda, M.; Asano, Y.
S-stereoselective piperazine-2-tert-butylcarboxamide hydrolase from Pseudomonas azotoformans IAM 1603 is a novel L-amino acid amidase
Eur. J. Biochem.
271
1465-1475
2004
Pseudomonas azotoformans (Q76KX0), Pseudomonas azotoformans IAM 1603 (Q76KX0)
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3.5.1.101 L-proline amide hydrolase
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