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Literature summary for 4.2.1.100 extracted from
- Promiscuous defluorinating enoyl-CoA hydratases/hydrolases allow for complete anaerobic degradation of 2-fluorobenzoate (2017), Front. Microbiol., 8, 2579 .
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| gene dch, recombinant expression of C-terminally His6-tagged enzyme in Escherichia coli strain MC4100 | Thauera aromatica |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 2-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O | Thauera aromatica | - |
2-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA | - |
r |  |
| 2-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O | Thauera aromatica K172 | - |
2-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA | - |
r | |
| 6-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O | Thauera aromatica | - |
6-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA | - |
r | |
| 6-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O | Thauera aromatica K172 | - |
6-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA | - |
r | |
| 6-hydroxycyclohexa-1-ene-1-carbonyl-CoA | Thauera aromatica | - |
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O | - |
r | |
| 6-hydroxycyclohexa-1-ene-1-carbonyl-CoA | Thauera aromatica K172 | - |
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O | - |
r | |
| cyclohexa-1,5-diene-1-carbonyl-CoA + H2O | Thauera aromatica | - |
6-hydroxycyclohexa-1-ene-1-carbonyl-CoA | - |
r | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Thauera aromatica | o87873 | - |
- |
| Thauera aromatica K172 | o87873 | - |
- |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| recombinant His6-tagged enzyme from Escherichia coli strain MC4100 by nickel affinity chromatography and desalting gel filtration | Thauera aromatica |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| additional information | 2-fluoro-benzoate- and benzoate-grown cells | Thauera aromatica | - |
Specific Activity [micromol/min/mg]
| Specific Activity Minimum [µmol/min/mg] | Specific Activity Maximum [µmol/min/mg] | Comment | Organism |
|---|---|---|---|
| 107 | - |
purified recombinant enzyme with substrate cyclohexa-1,5-diene-1-carbonyl-CoA, pH and temperature not specified in the publication | Thauera aromatica |
| 110 | - |
purified recombinant enzyme with substrate 6-hydroxycyclohex-1-ene-1-carbonyl-CoA, pH and temperature not specified in the publication | Thauera aromatica |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 2-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O | - |
Thauera aromatica | 2-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA | - |
r | |
| 2-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O | - |
Thauera aromatica K172 | 2-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA | - |
r | |
| 6-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O | - |
Thauera aromatica | 6-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA | - |
r | |
| 6-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O | - |
Thauera aromatica K172 | 6-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA | - |
r | |
| 6-hydroxycyclohexa-1-ene-1-carbonyl-CoA | - |
Thauera aromatica | cyclohexa-1,5-diene-1-carbonyl-CoA + H2O | - |
r | |
| 6-hydroxycyclohexa-1-ene-1-carbonyl-CoA | - |
Thauera aromatica K172 | cyclohexa-1,5-diene-1-carbonyl-CoA + H2O | - |
r | |
| cyclohexa-1,5-diene-1-carbonyl-CoA + H2O | - |
Thauera aromatica | 6-hydroxycyclohex-1-ene-1-carbonyl-CoA | - |
r | |
| cyclohexa-1,5-diene-1-carbonyl-CoA + H2O | - |
Thauera aromatica K172 | 6-hydroxycyclohex-1-ene-1-carbonyl-CoA | - |
r | |
| cyclohexa-1,5-diene-1-carbonyl-CoA + H2O | - |
Thauera aromatica | 6-hydroxycyclohexa-1-ene-1-carbonyl-CoA | - |
r | |
| additional information | the 1,5-dienoyl-CoA hydratase hydrated the fluorocyclohexa-1,5-dienoyl-CoA isomers to a mixture of the stable 2-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA and the unstable alpha-fluorohydrin 6-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA. The latter spontaneously decomposed to HF and 6-oxo-cyclohexa-1-ene-1-carbonyl-CoA | Thauera aromatica | ? | - |
? | |
| additional information | the 1,5-dienoyl-CoA hydratase hydrated the fluorocyclohexa-1,5-dienoyl-CoA isomers to a mixture of the stable 2-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA and the unstable alpha-fluorohydrin 6-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA. The latter spontaneously decomposed to HF and 6-oxo-cyclohexa-1-ene-1-carbonyl-CoA | Thauera aromatica K172 | ? | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| 1,5-dienoyl-CoA hydratase | - |
Thauera aromatica |
| DCH | - |
Thauera aromatica |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 30 | - |
in vivo assay at | Thauera aromatica |
General Information
| General Information | Comment | Organism |
|---|---|---|
| metabolism | the enzyme is involved in the biodegradation of the environmentally hazardous fluoroaromatics. The 1,5-dienoyl-CoA hydratase (DCH) hydrates the fluoro-1,5-dienoyl-CoA isomers to a mixture of the stable 2-fluoro-6-hydroxy-1-enoyl-CoA and the unstable alpha-fluorohydrin 6-fluoro-6-hydroxy-1-enoyl-CoA. The latter spontaneously decomposes to HF and 6-oxo-cyclohex-1-enoyl-CoA, a common intermediate of the benzoyl-coenzyme A (BzCoA) degradation pathway. 6-Oxo-cyclohex-1-enoyl-CoA hydrolase/hydratase catalyzes the defluorination of 2-fluoro-6-hydroxycyclohex-1-enoyl-CoA to 2-oxo-6-hydroxycyclohex-1-enoyl-CoA and HF again via water addition to an fluorocyclohex-1-enoyl-CoA functionality. Formation of both 3-fluorocyclohexa-1,5-diene-1-carbonyl-CoA and 5-fluorocyclohexa-1,5-diene-1-carbonyl-CoA suggesting a low regioselectivity of benzoyl-coenzyme A (BzCoA) reductase (BCR) for fluorinated BzCoA analogues. Enzyme DCH and bifunctional 6-oxo-cyclohex-1-enoyl-CoA hydrolase (OAH) both initiate defluorination of the 2-fluorocyclohexa-1,5-diene-1-carbonyl-CoA intermediate by 1,4-hydration. Enzyme OAH is competent to hydrate both fluorinated cyclohexa-1,5-diene-carbonyl-CoA isomers and exhibits a similar reactivity as enzyme DCH, and OAH alone is capable of defluorinating both fluorinated cyclohexa-1,5-diene-carbonyl-CoA isomers formed by BCR. Detailed pathway overview | Thauera aromatica |
| physiological function | the enzyme is involved in the biodegradation of the environmentally hazardous fluoroaromatics. The 1,5-dienoyl-CoA hydratase (DCH) hydrates the fluorocyclohexa-1,5-diene-1-carbonyl-CoA isomers to a mixture of the stable 2-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA and the unstable alpha-fluorohydrin 6-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA. The latter spontaneously decomposes to HF and 6-oxo-cyclohexa-1-ene-1-carbonyl-CoA, a common intermediate of the benzoyl-coenzyme A (BzCoA) degradation pathway. 6-Oxo-cyclohexa-1-ene-1-carbonyl-CoA hydrolase/hydratase catalyzes the defluorination of 2-fluoro-6-hydroxy-1-enoyl-CoA to 2-oxo-6-hydroxy-1-enoyl-CoA and HF again via water addition to an fluoro-enoyl-CoA functionality | Thauera aromatica |
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Release 2023.1 (January 2023)
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