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Literature summary for 3.5.2.6 extracted from

  • Kumar, S.; Adediran, S.A.; Nukaga, M.; Pratt, R.F.
    Kinetics of turnover of cefotaxime by the Enterobacter cloacae P99 and GCl beta-lactamases: two free enzyme forms of the P99 beta-lactamase detected by a combination of pre- and post-steady state kinetics (2004), Biochemistry, 43, 2664-2672.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
cefotaxime competitive inhibition of cephalothin hydrolysis; inhibits hydrolysis of cephalothin, P99 beta-lactamase Enterobacter cloacae
cefuroxime competitive inhibition of cephalothin hydrolysis Enterobacter cloacae

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
additional information combination of detailed post- and pre-steady state kinetics Enterobacter cloacae
0.0056
-
cefuroxime pH 7.5, 25°C, strain P99 Enterobacter cloacae
0.0056
-
cefuroxime P99 beta-lactamase Enterobacter cloacae
0.0081
-
cefotaxime pH 7.5, 25°C, strain GCI Enterobacter cloacae
0.0081
-
cefotaxime GC1 beta-lactamase Enterobacter cloacae
0.0154
-
cephalothin pH 7.5, 25°C, strain P99 Enterobacter cloacae
0.0154
-
cephalothin P99 beta-lactamase Enterobacter cloacae
0.0172
-
cefotaxime pH 7.5, 25°C, strain P99 Enterobacter cloacae
0.0172
-
cefotaxime P99 beta-lactamase Enterobacter cloacae
0.031
-
cephalothin pH 7.5, 25°C, strain GCI Enterobacter cloacae
0.031
-
cefuroxime GC1 beta-lactamase Enterobacter cloacae
0.046
-
3-[2-(2-aminothiazol-4-yl)2-(Z)-methoxyiminoacetylglycyl]oxybenzoic acid pH 7.5, 25°C, strain GCI Enterobacter cloacae
0.046
-
cephalothin GC1 beta-lactamase Enterobacter cloacae
0.059
-
3-[2-(2-aminothiazol-4-yl)2-(Z)-methoxyiminoacetylglycyl]oxybenzoic acid pH 7.5, 25°C, strain P99 Enterobacter cloacae
0.13
-
3-([N-(phenylacetyl)glycyl]oxy)benzoic acid pH 7.5, 25°C, strain GCI Enterobacter cloacae
0.13
-
3-([N-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]glycyl]oxy)benzoic acid GC1 beta-lactamase Enterobacter cloacae
0.23
-
3-([N-(phenylacetyl)glycyl]oxy)benzoic acid pH 7.5, 25°C, strain P99 Enterobacter cloacae
0.59
-
3-([N-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]glycyl]oxy)benzoic acid P99 beta-lactamase Enterobacter cloacae

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Enterobacter cloacae cephalosporins bearing oximino side chains are resistant to hydrolysis by class C enzymes, the side chain is necessary but not sufficent for production of resistance, it must be combinated with the dihydrothiazine ring ?
-
?
additional information Enterobacter cloacae P99 cephalosporins bearing oximino side chains are resistant to hydrolysis by class C enzymes, the side chain is necessary but not sufficent for production of resistance, it must be combinated with the dihydrothiazine ring ?
-
?
additional information Enterobacter cloacae GC1 cephalosporins bearing oximino side chains are resistant to hydrolysis by class C enzymes, the side chain is necessary but not sufficent for production of resistance, it must be combinated with the dihydrothiazine ring ?
-
?

Organism

Organism UniProt Comment Textmining
Enterobacter cloacae
-
-
-
Enterobacter cloacae
-
strains P99 and GCI, class C enzymes
-
Enterobacter cloacae GC1
-
-
-
Enterobacter cloacae P99
-
-
-

Reaction

Reaction Comment Organism Reaction ID
a beta-lactam + H2O = a substituted beta-amino acid reaction and kinetic mechanism Enterobacter cloacae

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3-([N-(phenylacetyl)glycyl]oxy)benzoic acid + H2O
-
Enterobacter cloacae ?
-
?
3-([N-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]glycyl]oxy)benzoic acid + H2O GC1 beta-lactamase Enterobacter cloacae ?
-
?
3-([N-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]glycyl]oxy)benzoic acid + H2O P99 beta-lactamase Enterobacter cloacae ?
-
?
3-[2-(2-aminothiazol-4-yl)2-(Z)-methoxyiminoacetylglycyl]oxybenzoic acid + H2O
-
Enterobacter cloacae ?
-
?
cefotaxime + H2O conformational restriction of the extended OMEGA loop in the enzyme is probably responsible for the long-living acyl-enzyme intermediate and transition effects of cefotaxime Enterobacter cloacae (2R)-5-[(acetyloxy)methyl]-2-[(R)-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino](carboxy)methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cefotaxime + H2O GC1 beta-lactamase Enterobacter cloacae (2R)-5-[(acetyloxy)methyl]-2-[(R)-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino](carboxy)methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cefotaxime + H2O poor substrate for P99 beta-lactamase Enterobacter cloacae (2R)-5-[(acetyloxy)methyl]-2-[(R)-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino](carboxy)methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cefuroxime + H2O
-
Enterobacter cloacae (2R)-5-[(carbamoyloxy)methyl]-2-[(R)-carboxy{[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetyl]amino}methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cefuroxime + H2O GC1 beta-lactamase Enterobacter cloacae (2R)-5-[(carbamoyloxy)methyl]-2-[(R)-carboxy{[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetyl]amino}methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cefuroxime + H2O poor substrate for P99 beta-lactamase Enterobacter cloacae (2R)-5-[(carbamoyloxy)methyl]-2-[(R)-carboxy{[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetyl]amino}methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cefuroxime + H2O
-
Enterobacter cloacae P99 (2R)-5-[(carbamoyloxy)methyl]-2-[(R)-carboxy{[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetyl]amino}methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cefuroxime + H2O
-
Enterobacter cloacae GC1 (2R)-5-[(carbamoyloxy)methyl]-2-[(R)-carboxy{[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetyl]amino}methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cephalothin + H2O best substrate Enterobacter cloacae (2R)-5-[(acetyloxy)methyl]-2-[(R)-carboxy[(thiophen-2-ylacetyl)amino]methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cephalothin + H2O GC1 beta-lactamase Enterobacter cloacae (2R)-5-[(acetyloxy)methyl]-2-[(R)-carboxy[(thiophen-2-ylacetyl)amino]methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cephalothin + H2O P99 beta-lactamase Enterobacter cloacae (2R)-5-[(acetyloxy)methyl]-2-[(R)-carboxy[(thiophen-2-ylacetyl)amino]methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cephalothin + H2O best substrate Enterobacter cloacae P99 (2R)-5-[(acetyloxy)methyl]-2-[(R)-carboxy[(thiophen-2-ylacetyl)amino]methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cephalothin + H2O GC1 beta-lactamase Enterobacter cloacae P99 (2R)-5-[(acetyloxy)methyl]-2-[(R)-carboxy[(thiophen-2-ylacetyl)amino]methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cephalothin + H2O P99 beta-lactamase Enterobacter cloacae P99 (2R)-5-[(acetyloxy)methyl]-2-[(R)-carboxy[(thiophen-2-ylacetyl)amino]methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cephalothin + H2O best substrate Enterobacter cloacae GC1 (2R)-5-[(acetyloxy)methyl]-2-[(R)-carboxy[(thiophen-2-ylacetyl)amino]methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cephalothin + H2O GC1 beta-lactamase Enterobacter cloacae GC1 (2R)-5-[(acetyloxy)methyl]-2-[(R)-carboxy[(thiophen-2-ylacetyl)amino]methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
cephalothin + H2O P99 beta-lactamase Enterobacter cloacae GC1 (2R)-5-[(acetyloxy)methyl]-2-[(R)-carboxy[(thiophen-2-ylacetyl)amino]methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
additional information cephalosporins bearing oximino side chains are resistant to hydrolysis by class C enzymes, the side chain is necessary but not sufficent for production of resistance, it must be combinated with the dihydrothiazine ring Enterobacter cloacae ?
-
?
additional information cephalosporins bearing oximino side chains are resistant to hydrolysis by class C enzymes, the side chain is necessary but not sufficent for production of resistance, it must be combinated with the dihydrothiazine ring Enterobacter cloacae P99 ?
-
?
additional information cephalosporins bearing oximino side chains are resistant to hydrolysis by class C enzymes, the side chain is necessary but not sufficent for production of resistance, it must be combinated with the dihydrothiazine ring Enterobacter cloacae GC1 ?
-
?

Synonyms

Synonyms Comment Organism
GC1 beta-lactamase
-
Enterobacter cloacae
P99 beta-lactamase
-
Enterobacter cloacae

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
assay at Enterobacter cloacae

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.28
-
cefuroxime pH 7.5, 25°C, strain P99 Enterobacter cloacae
0.28
-
cefuroxime P99 beta-lactamase Enterobacter cloacae
0.41
-
cefotaxime pH 7.5, 25°C, strain P99 Enterobacter cloacae
0.41
-
cefotaxime P99 beta-lactamase Enterobacter cloacae
11
-
3-[2-(2-aminothiazol-4-yl)2-(Z)-methoxyiminoacetylglycyl]oxybenzoic acid pH 7.5, 25°C, strain GCI Enterobacter cloacae
11
-
cephalothin GC1 beta-lactamase Enterobacter cloacae
11
-
3-([N-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]glycyl]oxy)benzoic acid GC1 beta-lactamase Enterobacter cloacae
19
-
3-[2-(2-aminothiazol-4-yl)2-(Z)-methoxyiminoacetylglycyl]oxybenzoic acid pH 7.5, 25°C, strain P99 Enterobacter cloacae
19
-
3-([N-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]glycyl]oxy)benzoic acid P99 beta-lactamase Enterobacter cloacae
25
-
3-([N-(phenylacetyl)glycyl]oxy)benzoic acid pH 7.5, 25°C, strain GCI Enterobacter cloacae
62
-
cefotaxime pH 7.5, 25°C, strain GCI Enterobacter cloacae
62
-
cefotaxime GC1 beta-lactamase Enterobacter cloacae
74.8
-
cephalothin pH 7.5, 25°C, strain GCI Enterobacter cloacae
74.8
-
cefuroxime GC1 beta-lactamase Enterobacter cloacae
125
-
3-([N-(phenylacetyl)glycyl]oxy)benzoic acid pH 7.5, 25°C, strain P99 Enterobacter cloacae
690
-
cephalothin pH 7.5, 25°C, strain P99 Enterobacter cloacae
690
-
cephalothin P99 beta-lactamase Enterobacter cloacae

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
assay at Enterobacter cloacae

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000013
-
cefuroxime versus cephalothin, pH 7.5, 25°C Enterobacter cloacae
0.000027
-
cefotaxime versus cephalothin, pH 7.5, 25°C Enterobacter cloacae