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Literature summary for 3.3.2.10 extracted from
- Tyrosine residues serve as proton donor in the catalytic mechanism of epoxide hydrolase from Agrobacterium radiobacter (2000), Biochemistry, 39, 5600-5613.
Protein Variants
| Protein Variants | Comment | Organism |
|---|---|---|
| Q134A | the Ki-value for phenylacetamide is 67fold higher than the Ki-value of the wild-type enzyme. The ratio of turnover number to KM-value for (R)-styrene oxide is 10fold lower than that of the wild-type enzyme. The ratio of turnover number to KM-value for (S)-styrene oxide is 25fold lower than that of the wild-type enzyme. The ratio of turnover number to KM-value for (R)-p-nitrostyrene oxide is 4fold lower than that of the wild-type enzyme. The ratio of turnover number to KM-value for (R)-p-nitrostyrene oxide is 13fold lower than that of the wild-type enzyme | Agrobacterium tumefaciens |
| Y152F | rate of irreversible inactivation for wild-type enzyme increases rapidly above pH 10, but the inactivation rates for Y215F and Y152F mutant remain low at increasing pH. The Ki-value for phenylacetamide is 67fold higher than the Ki-value of the wild-type enzyme | Agrobacterium tumefaciens |
| Y152F/Y215F | mutant enzyme with low activity, more thermostable than wild-type enzyme | Agrobacterium tumefaciens |
| Y215A | enzyme has lower enantioselectivity for styrene oxide and p-nitrostyrene oxide than the wild-type enzyme. The Ki-value for phenylacetamide is 9fold higher than the Ki-value of the wild-type enzyme. The ratio of turnover number to KM-value for (R)-styrene oxide is 2667fold lower than that of the wild-type enzyme. The ratio of turnover number to KM-value for (S)-styrene oxide is 2000fold lower than that of the wild-type enzyme. The ratio of turnover number to KM-value for (R)-p-nitrostyrene oxide is 486fold lower than that of the wild-type enzyme. The ratio of turnover number to KM-value for (R)-p-nitrostyrene oxide is 77fold lower than that of the wild-type enzyme | Agrobacterium tumefaciens |
| Y215F | more thermostable than wild-type enzyme. Rate of irreversible inactivation for wild-type enzyme increases rapidly above pH 10, but the inactivation rates for Y215F and Y152F mutant remain low at increasing pH. The Ki-value for phenylacetamide is 25fold higher than the Ki-value of the wild-type enzyme | Agrobacterium tumefaciens |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| acetamide | - |
Agrobacterium tumefaciens |  |
| Benzamide | - |
Agrobacterium tumefaciens | |
| Chloroacetamide | - |
Agrobacterium tumefaciens | |
| p-chlorobenzamide | - |
Agrobacterium tumefaciens | |
| p-nitrobenzamide | - |
Agrobacterium tumefaciens | |
| phenoxyacetamide | - |
Agrobacterium tumefaciens | |
| phenylacetamide | - |
Agrobacterium tumefaciens | |
| Phenylcarbamate | - |
Agrobacterium tumefaciens | |
| Urea | - |
Agrobacterium tumefaciens | |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.001 | - |
(R)-styrene oxide | pH 9.0, 30°C, mutant enzyme Q134A | Agrobacterium tumefaciens | |
| 0.009 | - |
(R)-p-nitrostyrene oxide | pH 9.0, 30°C, mutant enzyme Q134A | Agrobacterium tumefaciens | |
| 0.07 | - |
(S)-styrene oxide | pH 9.0, 30°C, mutant enzyme Q134A | Agrobacterium tumefaciens | |
| 0.6 | - |
(R)-styrene oxide | pH 9.0, 30°C, mutant enzyme Y215A | Agrobacterium tumefaciens | |
| 2.4 | - |
(S)-styrene oxide | pH 9.0, 30°C, mutant enzyme Y215A | Agrobacterium tumefaciens | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Agrobacterium tumefaciens | - |
AD1 | - |
| Agrobacterium tumefaciens AD1 | - |
AD1 | - |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| (R)-p-nitrostyrene oxide + H2O | - |
Agrobacterium tumefaciens | 1-(4-nitrophenyl)ethane-1,2-diol | - |
? | |
| (R)-p-nitrostyrene oxide + H2O | - |
Agrobacterium tumefaciens AD1 | 1-(4-nitrophenyl)ethane-1,2-diol | - |
? | |
| (R)-styrene oxide + H2O | - |
Agrobacterium tumefaciens | 1-phenylethane-1,2-diol | - |
? | |
| (R)-styrene oxide + H2O | - |
Agrobacterium tumefaciens AD1 | 1-phenylethane-1,2-diol | - |
? | |
| (S)-p-nitrostyrene oxide + H2O | - |
Agrobacterium tumefaciens | 1-(4-nitrophenyl)ethane-1,2-diol | - |
? | |
| (S)-p-nitrostyrene oxide + H2O | - |
Agrobacterium tumefaciens AD1 | 1-(4-nitrophenyl)ethane-1,2-diol | - |
? | |
| (S)-styrene oxide + H2O | - |
Agrobacterium tumefaciens | ? | - |
? | |
| (S)-styrene oxide + H2O | - |
Agrobacterium tumefaciens AD1 | ? | - |
? | |
Temperature Stability [°C]
| Temperature Stability Minimum [°C] | Temperature Stability Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 62 | 67 | precipitation of wild-type and mutant enzymes Y215F and Y152F/Y215F | Agrobacterium tumefaciens |
Turnover Number [1/s]
| Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.6 | - |
(S)-styrene oxide | pH 9.0, 30°C, mutant enzyme Y215A | Agrobacterium tumefaciens | |
| 0.8 | - |
(R)-styrene oxide | pH 9.0, 30°C, mutant enzyme Q134A | Agrobacterium tumefaciens | |
| 1.4 | - |
(S)-styrene oxide | pH 9.0, 30°C, mutant enzyme Q134A | Agrobacterium tumefaciens | |
| 1.7 | - |
(R)-styrene oxide | pH 9.0, 30°C, mutant enzyme Y215A | Agrobacterium tumefaciens | |
| 2.2 | - |
(R)-p-nitrostyrene oxide | pH 9.0, 30°C, mutant enzyme Q134A | Agrobacterium tumefaciens | |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 6 | 10 | reaction with (R)-p-nitrostyrene oxide, wild-type and mutant enzymes Y215F and Y152F | Agrobacterium tumefaciens |
pH Stability
| pH Stability | pH Stability Maximum | Comment | Organism |
|---|---|---|---|
| 10 | - |
rate of irreversible inactivation for wild-type enzyme increases rapidly above pH 10, but the inactivation rates for Y215F and Y152F mutant remain low at increasing pH | Agrobacterium tumefaciens |
Ki Value [mM]
| Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.03 | - |
phenylacetamide | pH 9.0, 30°C, wild-type enzyme | Agrobacterium tumefaciens | |
| 0.2 | - |
phenylacetamide | pH 9.0, 30°C, mutant enzyme Q134A | Agrobacterium tumefaciens | |
| 0.27 | - |
phenylacetamide | pH 9.0, 30°C, mutant enzyme Y215A | Agrobacterium tumefaciens | |
| 0.6 | - |
phenoxyacetamide | pH 9.0, 30°C, wild-type enzyme | Agrobacterium tumefaciens | |
| 0.75 | - |
phenylacetamide | pH 9.0, 30°C, mutant enzyme Y215F | Agrobacterium tumefaciens | |
| 1.1 | - |
Benzamide | pH 9.0, 30°C, wild-type enzyme | Agrobacterium tumefaciens | |
| 1.6 | - |
Phenylcarbamate | pH 9.0, 30°C, wild-type enzyme | Agrobacterium tumefaciens | |
| 2 | - |
phenylacetamide | pH 9.0, 30°C, mutant enzyme Y152F | Agrobacterium tumefaciens | |
| 2 | - |
p-nitrobenzamide | pH 9.0, 30°C, wild-type enzyme | Agrobacterium tumefaciens | |
| 3 | - |
p-chlorobenzamide | pH 9.0, 30°C, wild-type enzyme | Agrobacterium tumefaciens | |
| 3.5 | - |
Chloroacetamide | pH 9.0, 30°C, wild-type enzyme | Agrobacterium tumefaciens | |
| 5 | - |
Urea | pH 9.0, 30°C, wild-type enzyme | Agrobacterium tumefaciens | |
| 37 | - |
acetamide | pH 9.0, 30°C, wild-type enzyme | Agrobacterium tumefaciens | |
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Release 2023.1 (January 2023)
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