Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
2-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O
2-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
6-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
cyclohex-1-ene-1-carbonyl-CoA + H2O
2-hydroxycyclohexane-1-carbonyl-CoA
-
-
-
?
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-ene-1-carbonyl-CoA
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
-
-
-
r
cyclohexa-1,5-dienecarbonyl-CoA + H2O
6-hydroxycyclohex-1-ene-1-carbonyl-CoA
trans-1,4 water addition, stereochemistry of 6-hydroxycyclohex-1-ene-1-carboxyl-CoA by NMR analysis
-
-
?
cyclohexa-2,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-2-ene-1-carbonyl-CoA
-
only when dithionite is used as an artificial electron donor
-
?
additional information
?
-
2-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O
2-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
-
-
-
r
2-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O
2-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
-
-
-
r
6-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
-
-
-
r
6-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
-
-
-
r
6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
-
-
-
r
6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
-
-
-
r
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-ene-1-carbonyl-CoA
-
-
-
?
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-ene-1-carbonyl-CoA
-
-
-
?
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-ene-1-carbonyl-CoA
the enzyme is involved in benzoyl-coenzyme A degradation
-
-
?
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-ene-1-carbonyl-CoA
-
-
-
?
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-ene-1-carbonyl-CoA
the enzyme is involved in benzoyl-coenzyme A degradation
-
-
?
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-ene-1-carbonyl-CoA
-
-
-
r
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-ene-1-carbonyl-CoA
-
-
-
r
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-ene-1-carbonyl-CoA
-
-
-
r
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
-
-
-
-
?
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
-
-
-
-
r
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
-
involved in the benzoyl-CoA pathway
-
-
r
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
-
-
-
-
r
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
-
involved in the benzoyl-CoA pathway
-
-
r
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
-
-
-
-
r
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
-
involved in the benzoyl-CoA pathway
-
-
r
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
-
-
-
-
?
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
-
-
?
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
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
2-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O
2-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
6-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-ene-1-carbonyl-CoA
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
-
-
-
r
2-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O
2-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
-
-
-
r
2-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O
2-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
-
-
-
r
6-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
-
-
-
r
6-fluorocyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-fluoro-6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
-
-
-
r
6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
-
-
-
r
6-hydroxycyclohexa-1-ene-1-carbonyl-CoA
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
-
-
-
r
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-ene-1-carbonyl-CoA
the enzyme is involved in benzoyl-coenzyme A degradation
-
-
?
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-ene-1-carbonyl-CoA
the enzyme is involved in benzoyl-coenzyme A degradation
-
-
?
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
-
-
-
-
?
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
-
involved in the benzoyl-CoA pathway
-
-
r
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
-
involved in the benzoyl-CoA pathway
-
-
r
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
-
involved in the benzoyl-CoA pathway
-
-
r
cyclohexa-1,5-diene-1-carbonyl-CoA + H2O
6-hydroxycyclohex-1-enecarbonyl-CoA
-
-
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
1.8
-
cell extract, pH 7.5, 30°C
107
purified recombinant enzyme with substrate cyclohexa-1,5-diene-1-carbonyl-CoA, pH and temperature not specified in the publication
2
-
cell extract, pH 7.5, 30°C
2.5
-
cell extract, pH 7.5, 30°C
31.7
85°C, pH 7.0, highly enriched enzyme
350
-
purified enzyme, hydration reaction, pH 7.5, 30°C
550
-
purified enzyme, hydration reaction, pH 7.5, 30°C
730
-
purified enzyme, dehydration reaction, pH 7.5, 30°C
110
-
reversible reaction with 6-hydroxycyclohex-1-ene-1-carboxyl-CoA as substrat
110
purified recombinant enzyme with substrate 6-hydroxycyclohex-1-ene-1-carbonyl-CoA, pH and temperature not specified in the publication
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
metabolism
the enzyme is involved in benzoyl-coenzyme A degradation
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
metabolism
-
the enzyme is involved in benzoyl-coenzyme A degradation
-
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
-
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
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
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
28000
-
alpha2, 2 * 28000, SDS-PAGE
29900
-
4 * 30000, SDS-PAGE of purified His-tag labeled protein, 4 * 29900, calculated mass of the His-tag labeled protein, native mass by gel filtration
70000
-
Ferguson blot analysis
30000
-
2 * 30000, SDS-PAGE of purified His-tag labeled protein, 2 * 30400, calculated mass of the His-tag labeled protein, native mass by Ferguson blot analysis
30000
-
3 * 30000, SDS-PAGE of purified His-tag labeled protein, 3 * 30400, calculated mass of the His-tag labeled protein, native mass by gel filtration
30000
-
4 * 30000, SDS-PAGE of purified His-tag labeled protein, 4 * 29900, calculated mass of the His-tag labeled protein, native mass by gel filtration
30400
-
2 * 30000, SDS-PAGE of purified His-tag labeled protein, 2 * 30400, calculated mass of the His-tag labeled protein, native mass by Ferguson blot analysis
30400
-
3 * 30000, SDS-PAGE of purified His-tag labeled protein, 3 * 30400, calculated mass of the His-tag labeled protein, native mass by gel filtration
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Harwood, C.S.; Gibson, J.
Shedding light on anaerobic benzene ring degradation: a process unique to prokaryotes?
J. Bacteriol.
179
301-309
1997
Aromatoleum evansii, Thauera aromatica
brenda
Koch, J.; Eisenreich, W.; Bacher, A.; Fuchs, G.
Products of enzymatic reduction of benzoyl-CoA, a key reaction in anaerobic aromatic metabolism
Eur. J. Biochem.
211
649-661
1993
Aromatoleum evansii
brenda
Boll, M.; Laempe, D.; Eisenreich, W.; Bachers, A.; Mittelberger, T.; Heinze, J.; Fuchs, G.
Nonaromatic products from anoxic conversion of benzoyl-CoA with benzoyl-CoA reductase and cyclohexa-1,5-diene-1-carbonyl-CoA hydratase
J. Biol. Chem.
275
21889-21895
2000
Thauera aromatica
brenda
Lampe, D.; Eisenreich, W.; Bacher, A.; Fuchs, G.
Cyclohexa-1,5-diene-1-carboxyl-CoA hydratase, an enzyme involved in anaerobic metabolism of benzoyl-CoA in the denitrifying bacterium Thauera aromatica
Eur. J. Biochem.
255
618-627
1998
Thauera aromatica
brenda
Peters, F.; Shinoda, Y.; McInerney, M.J.; Boll, M.
Cyclohexa-1,5-diene-1-carbonyl-coenzyme A (CoA) hydratases of Geobacter metallireducens and Syntrophus aciditrophicus: Evidence for a common benzoyl-CoA degradation pathway in facultative and strict anaerobes
J. Bacteriol.
189
1055-1060
2007
Desulfococcus multivorans, Geobacter metallireducens, Syntrophus aciditrophicus
brenda
Thiele, B.; Rieder, O.; Golding, B.T.; Mueller, M.; Boll, M.
Mechanism of enzymatic Birch reduction: stereochemical course and exchange reactions of benzoyl-CoA reductase
J. Am. Chem. Soc.
130
14050-14051
2008
Thauera aromatica (o87873)
brenda
Schmid, G.; Rene, S.B.; Boll, M.
Enzymes of the benzoyl-coenzyme A degradation pathway in the hyperthermophilic archaeon Ferroglobus placidus
Environ. Microbiol.
17
3289-3300
2015
Ferroglobus placidus (D3RXI0), Ferroglobus placidus, Ferroglobus placidus DSM 10642 (D3RXI0)
brenda
Tiedt, O.; Mergelsberg, M.; Eisenreich, W.; Boll, M.
Promiscuous defluorinating enoyl-CoA hydratases/hydrolases allow for complete anaerobic degradation of 2-fluorobenzoate
Front. Microbiol.
8
2579
2017
Thauera aromatica (o87873), Thauera aromatica K172 (o87873)
brenda