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 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 | 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 | UniProt | Comment | Textmining |
---|---|---|---|
Enterobacter cloacae | - |
- |
- |
Enterobacter cloacae | - |
strains P99 and GCI, class C enzymes | - |
Enterobacter cloacae GC1 | - |
- |
- |
Enterobacter cloacae P99 | - |
- |
- |
Reaction | Comment | Organism | Reaction ID |
---|---|---|---|
a beta-lactam + H2O = a substituted beta-amino acid | reaction and kinetic mechanism | Enterobacter cloacae |
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 | Comment | Organism |
---|---|---|
GC1 beta-lactamase | - |
Enterobacter cloacae |
P99 beta-lactamase | - |
Enterobacter cloacae |
Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|
25 | - |
assay at | Enterobacter cloacae |
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 Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|
7.5 | - |
assay at | Enterobacter cloacae |
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 |