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Literature summary extracted from

  • Zhiryakova, D.; Guncheva, M.; Ivanov, I.; Stambolieva, N.
    Hydrolysis of phenylacetanilides catalyzed by penicillin G acylase from Alcaligenes faecalis: sensitivity of the reaction to substitution in the leaving group (2009), Catal. Commun., 11, 196-201.
No PubMed abstract available

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.5.1.11 additional information
-
 additional information kinetic results on the hydrolysis of a series of 4-substituted anilides catalyzed by penicillin G acylase from Alcaligenes faecalis Alcaligenes faecalis
3.5.1.11 0.095
-
 N-(4-nitrophenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 0.121
-
 N-(4-methylphenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 0.137
-
 N,2-diphenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 0.147
-
 2-phenyl-N-(4-sulfamoylphenyl)acetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 0.153
-
 ethyl 4-[(phenylacetyl)amino] benzoate pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 0.159
-
 N-[4-(methylsulfonyl)phenyl]-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 0.16
-
 N-(4-cyanophenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 0.162
-
 N-(4-methoxyphenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 0.171
-
 N-(4-bromophenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 0.23
-
 N-(4-acetylphenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis

Organism

EC Number Organism UniProt Comment Textmining
3.5.1.11 Alcaligenes faecalis
-
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
3.5.1.11 penicillin + H2O = a carboxylate + 6-aminopenicillanate structural model and catalytic mechanism, and energetics of the reaction, acylation is the rate-limiting step of hydrolysis. The collapse of the tetrahedral intermediate proceeds via synchronous bond breaking and formation, and the accumulation of charge on the amidic nitrogen due to the presence of a substituent is disfavored Alcaligenes faecalis
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.5.1.11 2-phenyl-N-(4-sulfamoylphenyl)acetamide + H2O
-
 Alcaligenes faecalis phenylacetate + 2-amino-4-sulfamoylphenol
-
 ?
3.5.1.11 ethyl 4-[(phenylacetyl)amino] benzoate + H2O
-
 Alcaligenes faecalis phenylacetate + 4-amino-ethylbenzoate
-
 ?
3.5.1.11 additional information substrate specificity with phenylacetyl p-substituted anilides, overview Alcaligenes faecalis ?
-
 ?
3.5.1.11 N,2-diphenylacetamide + H2O
-
 Alcaligenes faecalis phenylacetate + ?
-
 ?
3.5.1.11 N-(4-acetylphenyl)-2-phenylacetamide + H2O
-
 Alcaligenes faecalis phenylacetate + 2-amino-4-acetylphenol
-
 ?
3.5.1.11 N-(4-bromophenyl)-2-phenylacetamide + H2O
-
 Alcaligenes faecalis phenylacetate + 2-amino-4-bromophenol
-
 ?
3.5.1.11 N-(4-cyanophenyl)-2-phenylacetamide + H2O
-
 Alcaligenes faecalis phenylacetate + 2-amino-4-cyanophenol
-
 ?
3.5.1.11 N-(4-methoxyphenyl)-2-phenylacetamide + H2O
-
 Alcaligenes faecalis phenylacetate + 2-amino-4-methoxyphenol
-
 ?
3.5.1.11 N-(4-methylphenyl)-2-phenylacetamide + H2O
-
 Alcaligenes faecalis phenylacetate + 2-amino-4-methylphenol
-
 ?
3.5.1.11 N-(4-nitrophenyl)-2-phenylacetamide + H2O
-
 Alcaligenes faecalis phenylacetate + 2-amino-4-nitrophenol
-
 ?
3.5.1.11 N-[4-(methylsulfonyl)phenyl]-2-phenylacetamide + H2O
-
 Alcaligenes faecalis phenylacetate + 2-amino-4-(methylsulfonyl)phenol
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.5.1.11 More the enzyme belongs to the N-terminal-nucleophile superfamily Alcaligenes faecalis
3.5.1.11 penicillin G acylase
-
 Alcaligenes faecalis
3.5.1.11 PGA
-
 Alcaligenes faecalis

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.5.1.11 25
-
 assay at Alcaligenes faecalis

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3.5.1.11 15.14
-
 N-(4-nitrophenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 29.49
-
 N-[4-(methylsulfonyl)phenyl]-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 33.81
-
 N-(4-methoxyphenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 33.84
-
 N-(4-cyanophenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 35.94
-
 N-(4-acetylphenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 37.93
-
 N-(4-methylphenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 40.03
-
 2-phenyl-N-(4-sulfamoylphenyl)acetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 41.05
-
 ethyl 4-[(phenylacetyl)amino] benzoate pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 43.07
-
 N-(4-bromophenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 49.17
-
 N,2-diphenylacetamide pH 7.0, 25°C Alcaligenes faecalis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.5.1.11 7
-
 assay at Alcaligenes faecalis

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
3.5.1.11 156
-
 N-(4-acetylphenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 159
-
 N-(4-nitrophenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 185
-
 N-[4-(methylsulfonyl)phenyl]-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 209
-
 N-(4-methoxyphenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 212
-
 N-(4-cyanophenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 250
-
 N-(4-bromophenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 268
-
 ethyl 4-[(phenylacetyl)amino] benzoate pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 272
-
 2-phenyl-N-(4-sulfamoylphenyl)acetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 314
-
 N-(4-methylphenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
3.5.1.11 360
-
 N,2-diphenylacetamide pH 7.0, 25°C Alcaligenes faecalis