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Information on EC 3.5.1.14 - N-acyl-aliphatic-L-amino acid amidohydrolase
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3.5.1.14 N-acyl-aliphatic-L-amino acid amidohydrolaseIUBMB Comments
Contains Zn2+. The enzyme is found in animals and is involved in the hydrolysis of N-acylated or N-acetylated amino acids (except L-aspartate). It acts on mercapturic acids (S-conjugates of N-acetyl-L-cysteine) and neutral aliphatic N-acyl-alpha-amino acids. Some bacterial aminoacylases demonstrate substrate specificity of both EC 3.5.1.14 and EC 3.5.1.114. cf. EC 3.5.1.15, aspartoacylase and EC 3.5.1.114, N-acyl-aromatic-L-amino acid amidohydrolase.
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Word Map
- 3.5.1.14
-
n-acetylated
- synthesis
- n-acetyl-l-methionine
-
mercapturic
- acylases
-
cobalt-activated
- medicine
- diagnostics
- analysis
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
aminoacylase, acylase i, acy-1, aminoacylase i, aminoacylase 1, aminoacylase-1, l-aminoacylase, l-acy-1, aaiii, porcine kidney aminoacylase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
AA3
Acy1
acylase
-
-
-
-
acylase 1
acylase I
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-
-
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alpha-N-acylaminoacid hydrolase
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-
-
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amido acid deacylase
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-
-
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aminoacylase 1
aminoacylase 3
aminoacylase I
aminoacylase-1
benzamidase
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-
-
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dehydropeptidase II
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-
-
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fatty acid-amino acid conjugate hydrolyzing aminoacylase 1
hippurase
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-
-
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hippuricase
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-
-
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histozyme
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-
-
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L-ACY-1
L-amido-acid acylase
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-
-
-
L-aminoacylase
long acyl amidoacylase
-
-
-
-
M20
N-acyl-L-amino acid hydrolase
N-acyl-L-amino-acid amidohydrolase
pAcy1
short acyl amidoacylase
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-
-
-
additional information
aminoacylase I
-
-
-
-
L-aminoacylase
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-
-
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N-acyl-L-amino-acid amidohydrolase
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-
-
-
additional information
the enzyme is a member of the metalloprotein family M20
additional information
the enzyme belongs to the peptidase M20 family
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
an N-acetyl-L-cysteine-S-conjugate + H2O = an L-cysteine-S-conjugate + acetate
(2)
-
-
-
an N-acyl-aliphatic-L-amino acid + H2O = an aliphatic L-amino acid + a carboxylate
active site structure, catalysis involves residues H206, N263, R276, and D274, the dimerization domain residues play important roles in binding and catalysis, overview
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an N-acyl-aliphatic-L-amino acid + H2O = an aliphatic L-amino acid + a carboxylate
active site structure, molecular modelling to determine Asp82 function in catalysis, Asp82 ensures a proper protonation of the catalytic His residue, overview
an N-acyl-aliphatic-L-amino acid + H2O = an aliphatic L-amino acid + a carboxylate
(1)
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
deacylation
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-
-
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hydrolysis of amide bond
-
-
-
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hydrolysis of N-acetylated amino acids
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
N-acyl-aliphatic-L-amino acid amidohydrolase (carboxylate-forming)
Contains Zn2+. The enzyme is found in animals and is involved in the hydrolysis of N-acylated or N-acetylated amino acids (except L-aspartate). It acts on mercapturic acids (S-conjugates of N-acetyl-L-cysteine) and neutral aliphatic N-acyl-alpha-amino acids. Some bacterial aminoacylases demonstrate substrate specificity of both EC 3.5.1.14 and EC 3.5.1.114. cf. EC 3.5.1.15, aspartoacylase and EC 3.5.1.114, N-acyl-aromatic-L-amino acid amidohydrolase.
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CAS REGISTRY NUMBER
COMMENTARY
9012-37-7
-
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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
(2-chloroacetamido)(phenyl)acetate + H2O
chloroacetate + amino(phenyl)acetate
-
-
-
-
?
2-acetylamino-3-((1S,2S)-2-hydroxycyclohexylsulfanyl)-propionic acid + H2O
S-[(1S,2S)-2-hydroxycyclohexyl]cysteine + acetate
2-acetylamino-3-((1S,2S)-2-hydroxycyclooctylsulfanyl)-propionic acid + H2O
S-[(1S,2S)-2-hydroxycyclooctyl]cysteine + acetate
-
-
-
?
2-acetylamino-3-((3S,4S)-3-hydroxy-2,2-dimethyl-chroman-4-ylsulfanyl)-propionic acid + H2O
S-[(3S,4S)-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-4-yl]cysteine + acetate
2-acetylamino-3-[(S)-1-((R)-hydroxyphenyl-methyl)-2-oxo-2-phenyl-ethylsulfanyl]-propionic acid + H2O
S-[(1R,2R)-1-hydroxy-3-oxo-1,3-diphenylpropan-2-yl]cysteine + acetate
3-(2-furyl)acryloyl-L-methionine + H2O
3-(2-furyl)acrylate + L-methionine
-
-
-
?
benzoyl-DL-leucinamide + H2O
benzoate + DL-leucinamide
-
-
-
-
?
chloracetyl-DL-aminoheptylic acid + H2O
chloroacetate + DL-aminoheptanoate
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-
-
-
?
chloroacetyl-L-4-fluorophenylalanine + H2O
chloroacetate + L-4-fluorophenylalanine
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-
-
-
?
chloroacetyl-L-4-methoxyphenylalanine + H2O
chloroacetate + L-4-methoxyphenylalanine
-
-
-
-
?
DL-N-acetyl-D,L-3-(4-thiazolyl)alanine + H2O
L-3-(4-thiazolyl)alanine + D-N-acetyl-D-3-(4-thiazolyl)alanine
-
-
-
-
?
hydroxyacetyl-DL-alanine + H2O
hydroxyacetate + DL-alanine
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isolated as the barium salt
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-
?
methyl-mercaptoacetyl-DL-alanine + H2O
methylmercaptoacetate + DL-alanine
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-
-
-
?
methylmercaptoacetyl-DL-phenylalanine + H2O
methylmercaptoacetate + DL-phenylalanine
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-
-
-
?
N-(E)-3-methyl-2-hexenoyl-L-glutamine + H2O
(E)-3-methyl-2-hexenoyl-glutamine + L-glutamine
N-3-methyl-3-hydroxy-hexanoyl-L-glutamine + H2O
3-methyl-3-hydroxy-hexanoate + L-glutamine
N-acetyl-D-Homophenylalanine + H2O
acetate + D-Homophenylalanine
-
-
-
-
?
N-acetyl-DL-methionine + H2O
N-acetyl-D-methionine + L-methionine + acetic acid
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-
-
-
?
N-acetyl-DL-phenylglycine + H2O
DL-phenylglycine + acetate
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only D-isomer hydrolyzed
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-
?
N-acetyl-L-aspartate + H2O
acetate + L-aspartate
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no activity of wild type protein, mutant E167R protein shows activity
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-
?
N-acetyl-L-Homophenylalanine + H2O
acetate + L-Homophenylalanine
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-
-
-
?
N-acetyl-L-Phe methyl ester + H2O
acetate + L-Phe methyl ester
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the enzyme also shows esterase activity with N-acetyl-L-Phe methyl ester
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-
?
N-acetyl-L-phenylalanine methyl ester + H2O
acetate + L-phenylalanine methyl ester
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-
-
-
?
N-acetyl-O-benzyl-DL-serine + H2O
acetate + O-benzyl-DL-serine
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no hydrolysis with immobilized enzyme
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-
?
N-acetyl-S-(1,1,2,2-tetrafluoroethyl)-L-cysteine + H2O
acetate + S-(1,1,2,2-tetrafluoroethyl)-L-cysteine
-
-
-
?
N-acetyl-S-(1,2,2-trichlorovinyl)-L-cysteine + H2O
acetate + S-(1,2,2-trichlorovinyl)-L-cysteine
-
-
-
?
N-acetyl-S-(1,2,3,4,4-pentachlorobutadienyl)-L-cysteine + H2O
acetate + S-(1,2,3,4,4-pentachlorobutadienyl)-L-cysteine
-
-
-
?
N-acetyl-S-(1,2-dichlorovinyl)-L-cysteine + H2O
acetate + S-(1,2-dichlorovinyl)-L-cysteine
-
-
-
?
N-acetyl-S-(2,2-dichloro-1,1-difluoroethyl)-L-cysteine + H2O
acetate + S-(2,2-dichloro-1,1-difluoroethyl)-L-cysteine
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-
-
?
N-acetyl-S-(2,2-dichlorovinyl)-L-cysteine + H2O
acetate + S-(2,2-dichlorovinyl)-L-cysteine
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-
-
?
N-acetyl-S-(2,2-difluoro-1,1-dichloroethyl)-L-cysteine + H2O
acetate + S-(2,2-difluoro-1,1-dichloroethyl)-L-cysteine
-
-
-
?
N-acetyl-S-(2-chloro-1,1,2-trifluoroethyl)-L-cysteine + H2O
acetate + S-(2-chloro-1,1,2-trifluoroethyl)-L-cysteine
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-
-
?
N-acetyl-S-(2-chlorobenzyl)-L-cysteine + H2O
acetate + S-(2-chlorobenzyl)-L-cysteine
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-
-
?
N-acetyl-S-(2-fluorobenzyl)-L-cysteine + H2O
acetate + S-(2-fluorobenzyl)-L-cysteine
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-
-
?
N-acetyl-S-(3-fluorobenzyl)-L-cysteine + H2O
acetate + S-(3-fluorobenzyl)-L-cysteine
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-
-
?
N-acetyl-S-(4-bromobenzyl)-L-cysteine + H2O
acetate + S-(4-bromobenzyl)-L-cysteine
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-
-
?
N-acetyl-S-(4-chlorobenzyl)-L-cysteine + H2O
acetate + S-(4-chlorobenzyl)-L-cysteine
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-
-
?
N-acetyl-S-(4-methoxybenzyl)-L-cysteine + H2O
acetate + S-(4-methoxybenzyl)-L-cysteine
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-
-
?
N-acetyl-S-1,2-dichlorovinyl-L-cysteine + H2O
acetate + S-1,2-dichlorovinyl-L-cysteine
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-
-
-
?
N-acetylmethionine + H2O
acetate + L-methionine
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preferred substrate
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-
?
N-acetylpipecolic acid + H2O
acetate + L-piperidine-2-carboxylate
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-
-
-
?
N-alpha-benzoyl-L-phenylalanine + H2O
benzoate + L-phenylalanine
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-
-
-
?
N-alpha-chloroacetyl-L-phenylalanine + H2O
chloroacetate + L-phenylalanine
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-
-
-
?
N-benzoyl-L-arginine + H2O
benzoate + L-arginine
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immobilised enzyme
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-
?
N-benzoyl-L-leucine + H2O
benzoate + L-leucine
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immobilised enzyme
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-
?
N-benzoyl-L-threonine + H2O
benzoate + L-threonine
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immobilised enzyme
-
-
?
N-benzyloxycarbonyl-L-Phe-Gly + H2O
benzyl hydrogencarbonate + L-Phe-Gly
-
-
-
-
?
N-benzyloxycarbonyl-L-phenylalanine + H2O
benzyl hydrogencarbonate + L-phenylalanine
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-
-
-
?
N-benzyloxycarbonyl-L-phenylalanine + H2O
benzyloxycarbonate + L-phenylalanine
-
33.9% of the activity with N-acetyl-L-phenylalanine. no activity with N-benzyloxycarbonyl-D-phenylalanine
-
-
?
N-benzyloxycarbonyl-L-valine + H2O
benzyl hydrogencarbonate + L-valine
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-
-
-
?
N-CBZ-L-phenylalanine + H2O
? + L-phenylalanine
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immobilised enzyme
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-
?
N-chloroacetyl-2-amino-2-cyclohexylacetate + H2O
chloroacetate + 2-amino-2-cyclohexylacetate
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-
-
-
?
N-chloroacetyl-2-amino-3-cyclohexylpropionate + H2O
chloroacetate + 2-amino-3-cyclohexylpropionate
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-
-
-
?
N-chloroacetyl-2-amino-4-cyclohexylbutyrate + H2O
chloroacetate + 2-amino-4-cyclohexylbutyrate
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-
-
-
?
N-chloroacetyl-DL-norvaline + H2O
chloroacetate + DL-norvaline
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N-acylated racemic amino acids, pure acylated D forms hydrolyzed 10000-40000 times more slowly than corresponding pure acylated L isomers
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-
?