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Literature summary for 5.3.2.6 extracted from
- Chemical and enzymatic ketonization of 2-hydroxymuconate, a conjugated enol (1991), J. Am. Chem. Soc., 113, 3154-3162.
No PubMed abstract available
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| recombinant expression in Escherichia coli | Pseudomonas putida |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| additional information | - |
additional information | kinetic modeling, overview | Pseudomonas putida | |
| 0.145 | - |
2-hydroxymuconate | pH 7.3, 30°C | Pseudomonas putida |  |
| 0.189 | - |
2-oxo-3-hexenedioate | pH 7.3, 30°C | Pseudomonas putida | |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 2-hydroxymuconate | Pseudomonas putida | the conjugated enol, 2-hydroxymuconate is an unusually stable dienol that is reportedly generated in the course of bacterial catabolism of catechol by the enzymes of the meta-fission pathway | 2-oxo-3-hexenedioate | the dienol ketonizes chemically in aqueous solution and enzymatically by the action of 4-oxalocrotonate tautomerase to either the beta,gamma-unsaturated ketone or its alpha,beta-conjugated isomer 2-oxo-3-trans-hexenedioate | r | |
| 2-hydroxymuconate | Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 | the conjugated enol, 2-hydroxymuconate is an unusually stable dienol that is reportedly generated in the course of bacterial catabolism of catechol by the enzymes of the meta-fission pathway | 2-oxo-3-hexenedioate | the dienol ketonizes chemically in aqueous solution and enzymatically by the action of 4-oxalocrotonate tautomerase to either the beta,gamma-unsaturated ketone or its alpha,beta-conjugated isomer 2-oxo-3-trans-hexenedioate | r | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Pseudomonas putida | - |
- |
- |
| Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 | - |
- |
- |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| recombinant enzyme from Escherichia coli by ultracentrifugation, two different steps of anion exchange chromatography, hydroxylapatite and hydrophobic interaction chromatography, and gel filtration with alternating steps of ultrafiltration | Pseudomonas putida |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 2-hydroxy-4-trans-hexenedioate | - |
Pseudomonas putida | ? | - |
? | |
| 2-hydroxy-4-trans-hexenedioate | - |
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 | ? | - |
? | |
| 2-hydroxymuconate | ketonization | Pseudomonas putida | 2-oxo-3-hexenedioate | - |
r | |
| 2-hydroxymuconate | the conjugated enol, 2-hydroxymuconate is an unusually stable dienol that is reportedly generated in the course of bacterial catabolism of catechol by the enzymes of the meta-fission pathway | Pseudomonas putida | 2-oxo-3-hexenedioate | the dienol ketonizes chemically in aqueous solution and enzymatically by the action of 4-oxalocrotonate tautomerase to either the beta,gamma-unsaturated ketone or its alpha,beta-conjugated isomer 2-oxo-3-trans-hexenedioate | r | |
| 2-hydroxymuconate | ketonization | Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 | 2-oxo-3-hexenedioate | - |
r | |
| 2-hydroxymuconate | the conjugated enol, 2-hydroxymuconate is an unusually stable dienol that is reportedly generated in the course of bacterial catabolism of catechol by the enzymes of the meta-fission pathway | Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 | 2-oxo-3-hexenedioate | the dienol ketonizes chemically in aqueous solution and enzymatically by the action of 4-oxalocrotonate tautomerase to either the beta,gamma-unsaturated ketone or its alpha,beta-conjugated isomer 2-oxo-3-trans-hexenedioate | r | |
| 2-oxo-3-hexenedioate | - |
Pseudomonas putida | 2-oxo-3-trans-hexenedioate | - |
? | |
| 2-oxo-3-hexenedioate | - |
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 | 2-oxo-3-trans-hexenedioate | - |
? | |
| additional information | substrate specificity, overview | Pseudomonas putida | ? | - |
? | |
| additional information | substrate specificity, overview | Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 | ? | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| 4-OT | - |
Pseudomonas putida |
| 4-oxalocrotonate tautomerase | - |
Pseudomonas putida |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 30 | - |
assay at | Pseudomonas putida |
Turnover Number [1/s]
| Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 139000 | - |
2-hydroxymuconate | pH 7.3, 30°C | Pseudomonas putida | |
| 288000 | - |
2-oxo-3-hexenedioate | pH 7.3, 30°C | Pseudomonas putida | |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 7.3 | - |
assay at | Pseudomonas putida |
General Information
| General Information | Comment | Organism |
|---|---|---|
| additional information | immediate nonenzymatic conversion of 2-oxo-3-hexenedioate to 2-hydroxy-3-trans-hexenedioate with NaBH4. Rate constants for the nonenzymatic phosphate-catalyzed ketonization of 2-hydroxymuconate, overview | Pseudomonas putida |
| physiological function | 4-oxalocrotonate tautomerase is an extremely efficient catalyst apparently processing either isomer near the diffusion control limit of a small molecule and an enzyme | Pseudomonas putida |
kcat/KM [mM/s]
| kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 957000 | - |
2-hydroxymuconate | pH 7.3, 30°C | Pseudomonas putida | |
| 1520000 | - |
2-oxo-3-hexenedioate | pH 7.3, 30°C | Pseudomonas putida | |
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