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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
-
-
?
(S)-piperidine-2-carboxamide + H2O
(S)-piperidine-2-carboxylic acid + NH3
32% of the activity with L-proline amide
-
-
?
L-alanine amide + H2O
L-alanine + NH3
10.6% of the activity with L-proline amide
-
-
?
L-isoleucine amide + H2O
L-isoleucine + NH3
0.17% of the activity with L-proline amide
-
-
?
L-leucine amide + H2O
L-leucine + NH3
L-methionine amide + H2O
L-methionine + NH3
4.2% of the activity with L-proline amide
-
-
?
L-phenylalanine amide + H2O
L-phenylalanine + NH3
L-proline amide + H2O
L-proline + NH3
-
-
-
?
L-proline-p-nitroanilide + H2O
? + NH3
40.9% of the activity with L-proline amide
-
-
?
L-serine amide + H2O
L-serine + NH3
0.43% of the activity with L-proline amide
-
-
?
L-threonine amide + H2O
L-threonine + NH3
0.12% of the activity with L-proline amide
-
-
?
L-tryptophan amide + H2O
L-tryptophan + NH3
0.2% of the activity with L-proline amide
-
-
?
L-tyrosine amide + H2O
L-tyrosine + NH3
0.086% of the activity with L-proline amide
-
-
?
additional information
?
-
(R,S)-piperazine-2-tert-butylcarboxamide + H2O

(S)-piperazine-2-tert-butylcarboxylic acid + NH3
% of the activity with L-proline amide
-
-
?
(R,S)-piperazine-2-tert-butylcarboxamide + H2O
(S)-piperazine-2-tert-butylcarboxylic acid + NH3
% of the activity with L-proline amide
-
-
?
(S)-piperazine-2-carboxamide + H2O

(S)-piperazine-2-carboxylic acid + NH3
3.7% of the activity with L-proline amide
-
-
?
(S)-piperazine-2-carboxamide + H2O
(S)-piperazine-2-carboxylic acid + NH3
3.7% of the activity with L-proline amide
-
-
?
L-leucine amide + H2O

L-leucine + NH3
0.46% of the activity with L-proline amide
-
-
?
L-leucine amide + H2O
L-leucine + NH3
0.46% of the activity with L-proline amide
-
-
?
L-phenylalanine amide + H2O

L-phenylalanine + NH3
0.97% of the activity with L-proline amide
-
-
?
L-phenylalanine amide + H2O
L-phenylalanine + NH3
0.97% of the activity with L-proline amide
-
-
?
additional information

?
-
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
-
-
?
additional information
?
-
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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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
-
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)
brenda