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Literature summary 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

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

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.5.2.6 additional information
-
 additional information combination of detailed post- and pre-steady state kinetics Enterobacter cloacae
3.5.2.6 0.0056
-
 cefuroxime pH 7.5, 25°C, strain P99 Enterobacter cloacae
3.5.2.6 0.0056
-
 cefuroxime P99 beta-lactamase Enterobacter cloacae
3.5.2.6 0.0081
-
 cefotaxime pH 7.5, 25°C, strain GCI Enterobacter cloacae
3.5.2.6 0.0081
-
 cefotaxime GC1 beta-lactamase Enterobacter cloacae
3.5.2.6 0.0154
-
 cephalothin pH 7.5, 25°C, strain P99 Enterobacter cloacae
3.5.2.6 0.0154
-
 cephalothin P99 beta-lactamase Enterobacter cloacae
3.5.2.6 0.0172
-
 cefotaxime pH 7.5, 25°C, strain P99 Enterobacter cloacae
3.5.2.6 0.0172
-
 cefotaxime P99 beta-lactamase Enterobacter cloacae
3.5.2.6 0.031
-
 cephalothin pH 7.5, 25°C, strain GCI Enterobacter cloacae
3.5.2.6 0.031
-
 cefuroxime GC1 beta-lactamase Enterobacter cloacae
3.5.2.6 0.046
-
 3-[2-(2-aminothiazol-4-yl)2-(Z)-methoxyiminoacetylglycyl]oxybenzoic acid pH 7.5, 25°C, strain GCI Enterobacter cloacae
3.5.2.6 0.046
-
 cephalothin GC1 beta-lactamase Enterobacter cloacae
3.5.2.6 0.059
-
 3-[2-(2-aminothiazol-4-yl)2-(Z)-methoxyiminoacetylglycyl]oxybenzoic acid pH 7.5, 25°C, strain P99 Enterobacter cloacae
3.5.2.6 0.13
-
 3-([N-(phenylacetyl)glycyl]oxy)benzoic acid pH 7.5, 25°C, strain GCI Enterobacter cloacae
3.5.2.6 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
3.5.2.6 0.23
-
 3-([N-(phenylacetyl)glycyl]oxy)benzoic acid pH 7.5, 25°C, strain P99 Enterobacter cloacae
3.5.2.6 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)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.5.2.6 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 ?
-
 ?
3.5.2.6 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 ?
-
 ?
3.5.2.6 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

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

Reaction

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

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.5.2.6 3-([N-(phenylacetyl)glycyl]oxy)benzoic acid + H2O
-
 Enterobacter cloacae ?
-
 ?
3.5.2.6 3-([N-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]glycyl]oxy)benzoic acid + H2O GC1 beta-lactamase Enterobacter cloacae ?
-
 ?
3.5.2.6 3-([N-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]glycyl]oxy)benzoic acid + H2O P99 beta-lactamase Enterobacter cloacae ?
-
 ?
3.5.2.6 3-[2-(2-aminothiazol-4-yl)2-(Z)-methoxyiminoacetylglycyl]oxybenzoic acid + H2O
-
 Enterobacter cloacae ?
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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
-
 ?
3.5.2.6 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 ?
-
 ?
3.5.2.6 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 ?
-
 ?
3.5.2.6 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

EC Number Synonyms Comment Organism
3.5.2.6 GC1 beta-lactamase
-
 Enterobacter cloacae
3.5.2.6 P99 beta-lactamase
-
 Enterobacter cloacae

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.5.2.6 25
-
 assay at Enterobacter cloacae

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3.5.2.6 0.28
-
 cefuroxime pH 7.5, 25°C, strain P99 Enterobacter cloacae
3.5.2.6 0.28
-
 cefuroxime P99 beta-lactamase Enterobacter cloacae
3.5.2.6 0.41
-
 cefotaxime pH 7.5, 25°C, strain P99 Enterobacter cloacae
3.5.2.6 0.41
-
 cefotaxime P99 beta-lactamase Enterobacter cloacae
3.5.2.6 11
-
 3-[2-(2-aminothiazol-4-yl)2-(Z)-methoxyiminoacetylglycyl]oxybenzoic acid pH 7.5, 25°C, strain GCI Enterobacter cloacae
3.5.2.6 11
-
 cephalothin GC1 beta-lactamase Enterobacter cloacae
3.5.2.6 11
-
 3-([N-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]glycyl]oxy)benzoic acid GC1 beta-lactamase Enterobacter cloacae
3.5.2.6 19
-
 3-[2-(2-aminothiazol-4-yl)2-(Z)-methoxyiminoacetylglycyl]oxybenzoic acid pH 7.5, 25°C, strain P99 Enterobacter cloacae
3.5.2.6 19
-
 3-([N-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]glycyl]oxy)benzoic acid P99 beta-lactamase Enterobacter cloacae
3.5.2.6 25
-
 3-([N-(phenylacetyl)glycyl]oxy)benzoic acid pH 7.5, 25°C, strain GCI Enterobacter cloacae
3.5.2.6 62
-
 cefotaxime pH 7.5, 25°C, strain GCI Enterobacter cloacae
3.5.2.6 62
-
 cefotaxime GC1 beta-lactamase Enterobacter cloacae
3.5.2.6 74.8
-
 cephalothin pH 7.5, 25°C, strain GCI Enterobacter cloacae
3.5.2.6 74.8
-
 cefuroxime GC1 beta-lactamase Enterobacter cloacae
3.5.2.6 125
-
 3-([N-(phenylacetyl)glycyl]oxy)benzoic acid pH 7.5, 25°C, strain P99 Enterobacter cloacae
3.5.2.6 690
-
 cephalothin pH 7.5, 25°C, strain P99 Enterobacter cloacae
3.5.2.6 690
-
 cephalothin P99 beta-lactamase Enterobacter cloacae

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.5.2.6 7.5
-
 assay at Enterobacter cloacae

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
3.5.2.6 0.000013
-
 cefuroxime versus cephalothin, pH 7.5, 25°C Enterobacter cloacae
3.5.2.6 0.000027
-
 cefotaxime versus cephalothin, pH 7.5, 25°C Enterobacter cloacae