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Literature summary for 3.5.1.11 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
Search for more literature for 3.5.1.11

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
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
0.095
-
 N-(4-nitrophenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
0.121
-
 N-(4-methylphenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
0.137
-
 N,2-diphenylacetamide pH 7.0, 25°C Alcaligenes faecalis
0.147
-
 2-phenyl-N-(4-sulfamoylphenyl)acetamide pH 7.0, 25°C Alcaligenes faecalis
0.153
-
 ethyl 4-[(phenylacetyl)amino] benzoate pH 7.0, 25°C Alcaligenes faecalis
0.159
-
 N-[4-(methylsulfonyl)phenyl]-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
0.16
-
 N-(4-cyanophenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
0.162
-
 N-(4-methoxyphenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
0.171
-
 N-(4-bromophenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis
0.23
-
 N-(4-acetylphenyl)-2-phenylacetamide pH 7.0, 25°C Alcaligenes faecalis

Organism

Organism UniProt Comment Textmining
Alcaligenes faecalis
-
-
-

Reaction

Reaction Comment Organism Reaction ID
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)

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

Synonyms

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

Temperature Optimum [°C]

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

Turnover Number [1/s]

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

pH Optimum

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

kcat/KM [mM/s]

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