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Literature summary for 3.7.1.8 extracted from
- The catalytic serine of MCP hydrolases is activated differently for C-O bond cleavage than for C-C bond cleavage (2012), Biochemistry, 51, 5831-5840.
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| overexpression of wild-type and mutant BphDs in Escherichia coli strain Rosetta(DE3)pLysS | Paraburkholderia xenovorans |
Protein Variants
| Protein Variants | Comment | Organism |
|---|---|---|
| H265A | site-directed mutagenesis, the mutant shows highly reduced activity compared to the wild-type enzyme | Paraburkholderia xenovorans |
| H265Q | site-directed mutagenesis, the mutant shows highly reduced activity compared to the wild-type enzyme, rapid acylation of the variant during C-C bond cleavage suggesting that the serinate forms via a substrate-assisted mechanism in the reaction | Paraburkholderia xenovorans |
| S112A | site-directed mutagenesis, the mutant shows highly reduced activity compared to the wild-type enzyme | Paraburkholderia xenovorans |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| ethanol | - |
Paraburkholderia xenovorans |  |
| methanol | - |
Paraburkholderia xenovorans | |
| additional information | no effects by n-propanol and 2-propanol | Paraburkholderia xenovorans |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| additional information | - |
additional information | in the steady-state hydrolysis of HOPDA, kcat/Km values are independent of methanol concentration, while both kcat and Km values increase with methanol concentration, stopped-flow spectrophotometry and steady-state kinetics, overview | Paraburkholderia xenovorans | |
| 0.0002 | - |
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid | pH 7.5, 25°C, recombinant wild-type BphD, without methanol | Paraburkholderia xenovorans | |
| 0.00085 | - |
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid | pH 7.5, 25°C, recombinant wild-type BphD, with 494 mM methanol | Paraburkholderia xenovorans | |
| 0.002 | - |
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid | pH 7.5, 25°C, recombinant wild-type BphD, with 12940 mM methanol | Paraburkholderia xenovorans | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Paraburkholderia xenovorans | - |
gene bphD | - |
Reaction
| Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|
| 2,6-dioxo-6-phenylhexa-3-enoate + H2O = benzoate + 2-oxopent-4-enoate | general base and nucleophilic catalytic reaction mechanisms, overview | Paraburkholderia xenovorans |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O | i.e. HOPDA | Paraburkholderia xenovorans | ? | - |
? | |
| 4-nitrophenyl benzoate + H2O | the serine nucleophile is activated by the His-Asp dyad | Paraburkholderia xenovorans | 4-nitrophenol + benzoate | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| BphD | - |
Paraburkholderia xenovorans |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 25 | - |
assay at | Paraburkholderia xenovorans |
Turnover Number [1/s]
| Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| additional information | - |
additional information | in the steady-state hydrolysis of HOPDA, kcat/Km values are independent of methanol concentration, while both kcat and Km values increase with methanol concentration, stopped-flow spectrophotometry and steady-state kinetics, overview | Paraburkholderia xenovorans | |
| 2 | 8 | 2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid | pH 7.5, 25°C, recombinant wild-type BphD, with 12940 mM methanol | Paraburkholderia xenovorans | |
| 6.3 | - |
4-nitrophenyl benzoate | pH 7.5, 25°C | Paraburkholderia xenovorans | |
| 6.5 | - |
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid | pH 7.5, 25°C, recombinant wild-type BphD, without methanol | Paraburkholderia xenovorans | |
| 26 | - |
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid | pH 7.5, 25°C, recombinant wild-type BphD, with 494 mM methanol | Paraburkholderia xenovorans | |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 7.5 | - |
assay at | Paraburkholderia xenovorans |
General Information
| General Information | Comment | Organism |
|---|---|---|
| malfunction | rapid acylation of the H265Q variant during C-C bond cleavage suggests that the serinate forms via a substrate-assisted mechanism in the reaction | Paraburkholderia xenovorans |
| metabolism | BphD is a meta-cleavage product (MCP) hydrolase which catalyzes C-C bond fission in the aerobic catabolism of aromatic compounds by bacteria utilizing a Ser-His-Asp triad to catalyze hydrolysis via an acyl-enzyme intermediate | Paraburkholderia xenovorans |
kcat/KM [mM/s]
| kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 14 | - |
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid | pH 7.5, 25°C, recombinant wild-type BphD, with 12940 mM methanol | Paraburkholderia xenovorans | |
| 31 | - |
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid | pH 7.5, 25°C, recombinant wild-type BphD, with 494 mM methanol | Paraburkholderia xenovorans | |
| 32 | - |
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid | pH 7.5, 25°C, recombinant wild-type BphD, without methanol | Paraburkholderia xenovorans | |
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