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EC Tree
IUBMB Comments Also acts on crotonoyl thioesters of pantetheine and acyl-carrier protein.
The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Synonyms
crotonase, enoyl coenzyme a hydratase, cp 24, (r)-specific enoyl-coa hydratase, cacrt, 3-hydroxybutyryl-coa dehydratase,
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(R)-specific enoyl-CoA hydratase
D-3-Hydroxybutyryl coenzyme A dehydratase
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D-3-Hydroxybutyryl-CoA dehydratase
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Dehydratase, D-3-hydroxybutyryl coenzyme A
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Enoyl coenzyme A hydrase (D)
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enoyl coenzyme A hydratase
enoyl-CoA hydratase 2
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(R)-specific enoyl-CoA hydratase
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(R)-specific enoyl-CoA hydratase
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crotonase
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enoyl coenzyme A hydratase
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enoyl coenzyme A hydratase
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Ferp_1035
gene name. Bifunctional crotonase/3-OH-butyryl-CoA dehydrogenase
Ferp_1035
gene name. Bifunctional crotonase/3-OH-butyryl-CoA dehydrogenase
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phaJ
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(3R)-3-hydroxybutanoyl-CoA = crotonoyl-CoA + H2O
(3R)-3-hydroxybutanoyl-CoA = crotonoyl-CoA + H2O
stereochemistry
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(3R)-3-hydroxybutanoyl-CoA = crotonoyl-CoA + H2O
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(3R)-3-hydroxybutanoyl-CoA hydro-lyase (crotonoyl-CoA-forming)
Also acts on crotonoyl thioesters of pantetheine and acyl-carrier protein.
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(3R)-3-hydroxybutanoyl-CoA
crotonoyl-CoA + H2O
(3R)-3-hydroxybutanoyl-CoA
crotonyl-CoA + H2O
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3-hydroxybutyryl-CoA
crotonyl-CoA + H2O
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r
crotonoyl-CoA + H2O
(3R)-3-hydroxybutanoyl-CoA
crotonyl-CoA
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enzyme is involved in synthesis of poly-beta-hydroxybutyrate, lipid reserve of bacteria
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Crotonyl-CoA + H2O
(3R)-3-Hydroxybutanoyl-CoA
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Crotonyl-[acyl-carrier protein] + H2O
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about 50% of the activity with crotonyl-CoA
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Crotonylpantetheine
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about 55% of the activity with crotonyl-CoA
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trans-2-Hexenoyl-CoA + H2O
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about 35% of the activity with crotonyl-CoA
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additional information
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(3R)-3-hydroxybutanoyl-CoA
crotonoyl-CoA + H2O
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(3R)-3-hydroxybutanoyl-CoA
crotonoyl-CoA + H2O
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crotonoyl-CoA + H2O
(3R)-3-hydroxybutanoyl-CoA
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crotonoyl-CoA + H2O
(3R)-3-hydroxybutanoyl-CoA
the enzyme is involved in benzoyl-coenzyme A degradation
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crotonoyl-CoA + H2O
(3R)-3-hydroxybutanoyl-CoA
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crotonoyl-CoA + H2O
(3R)-3-hydroxybutanoyl-CoA
the enzyme is involved in benzoyl-coenzyme A degradation
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additional information
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enzyme residues Ser69 and Ala24 are signature residues of CaCRT, resulting in a distinct ADP binding mode wherein the ADP moiety of acetoacetyl-CoA is bound at a different position compared with other crotonases. The substrate specificity of crotonase enzymes is determined by both the structural feature of the a3 helix region and the residues contributing the enoyl-CoA binding pocket. A tightly formed a3 helix and two phenylalanine residues, Phe143 and Phe233, aid CaCRT to accommodate crotonyl-CoA as the substrate. Phe143 and Phe233 are key residues for the constitution of the crotonyl binding pocket to accommodate the four-carbon crotonyl-CoA as a substrate
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additional information
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2-enoyl-CoA hydratase 2 is the middle part of the mammalian multifunctional protein-2, MFP-2, which catalyzes the (R)-specific hydration of 2-enoyl-CoA thioesters
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additional information
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no activity with crotonylglutathione, acrylyl-CoA
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(3R)-3-hydroxybutanoyl-CoA
crotonoyl-CoA + H2O
crotonoyl-CoA + H2O
(3R)-3-hydroxybutanoyl-CoA
crotonyl-CoA
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enzyme is involved in synthesis of poly-beta-hydroxybutyrate, lipid reserve of bacteria
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additional information
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2-enoyl-CoA hydratase 2 is the middle part of the mammalian multifunctional protein-2, MFP-2, which catalyzes the (R)-specific hydration of 2-enoyl-CoA thioesters
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(3R)-3-hydroxybutanoyl-CoA
crotonoyl-CoA + H2O
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(3R)-3-hydroxybutanoyl-CoA
crotonoyl-CoA + H2O
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crotonoyl-CoA + H2O
(3R)-3-hydroxybutanoyl-CoA
the enzyme is involved in benzoyl-coenzyme A degradation
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crotonoyl-CoA + H2O
(3R)-3-hydroxybutanoyl-CoA
the enzyme is involved in benzoyl-coenzyme A degradation
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iodoacetamide
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0.01 M, 30% inhibition
iodoacetic acid
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0.01 M, 12% inhibition
N-ethylmaleimide
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0.01 M, 23% inhibition
oct-2-yn-4-enoyl-CoA
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a multifunctional irreversible enzyme inhibitor in fatty acid oxidation mainly targeting mitochondrial trifunctional protein beta-subunit, alsoirreversibly inactivates enoyl-CoA hydratase 2, mechanism for inactivation, overview
p-Substituted mercuribenzoate
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3 mM, 65% inhibition
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Colitis
Impairment of mitochondrial acetoacetyl CoA thiolase activity in the colonic mucosa of patients with ulcerative colitis.
Colitis, Ulcerative
Impairment of mitochondrial acetoacetyl CoA thiolase activity in the colonic mucosa of patients with ulcerative colitis.
Colitis, Ulcerative
Mucosal enzyme activity for butyrate oxidation; no defect in patients with ulcerative colitis.
Colonic Neoplasms
Impairment of mitochondrial acetoacetyl CoA thiolase activity in the colonic mucosa of patients with ulcerative colitis.
Colorectal Neoplasms
Expression of enoyl coenzyme A hydratase, short chain, 1, in colorectal cancer and its association with clinicopathological characteristics.
Cutis Laxa
Unique presentation of cutis laxa with Leigh-like syndrome due to ECHS1 deficiency.
Dehydration
(R)-lactyl-CoA dehydratase from Clostridium propionicum. Stereochemistry of the dehydration of (R)-2-hydroxybutyryl-CoA to crotonyl-CoA.
Dehydration
Isotope effects on the crotonase reaction.
Dehydration
Structural insights into substrate specificity of crotonase from the n-butanol producing bacterium Clostridium acetobutylicum.
Dehydration
The Structure of LiuC, a 3-Hydroxy-3-Methylglutaconyl CoA Dehydratase Involved in Isovaleryl-CoA Biosynthesis in Myxococcus xanthus, Reveals Insights into Specificity and Catalysis.
Metabolism, Inborn Errors
Unique presentation of cutis laxa with Leigh-like syndrome due to ECHS1 deficiency.
Muscle Spasticity
Effect of seat surface inclination on postural control during reaching in preterm children with cerebral palsy.
Myocardial Ischemia
Enoyl coenzyme a hydratase domain-containing 2, a potential novel regulator of myocardial ischemia injury.
Paratuberculosis
Use of enoyl coenzyme A hydratase of Mycobacterium avium subsp. paratuberculosis for the serological diagnosis of Johne's disease.
Sepsis
Lipid metabolic signatures deviate in sepsis survivors compared to non-survivors.
Starvation
Increased Fatty Acid beta-Oxidation after Glucose Starvation in Maize Root Tips.
Stomach Neoplasms
Attenuation of enoyl coenzyme A hydratase short chain 1 expression in gastric cancer cells inhibits cell proliferation and migration in vitro.
Tauopathies
Identification of non-Alzheimer's disease tauopathies-related proteins by proteomic analysis.
Tuberculosis
Mechanism of the Intramolecular Claisen Condensation Reaction Catalyzed by MenB, a Crotonase Superfamily Member.
Xeroderma Pigmentosum
[Screening of binding proteins to interferon-alpha promoter DNA by phage display technique]
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0.08
crotonyl-[acyl-carrier protein]
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0.118
Crotonylpantetheine
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0.0263
trans-2-hexenoyl-CoA
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0.025
oct-2-yn-4-enoyl-CoA
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ECH 2
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5.7
85°C, pH 7.0, highly enriched enzyme
additional information
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UniProt
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physiological function
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the enzyme catalyzes the dehydration of 3-hydroxybutyryl-CoA to crotonyl-CoA in the n-butanol biosynthetic pathway, molecular mechanism
additional information
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substrate binding pocket structure and mechanism, overview. CaCRT uses a unique CoA binding mode. The Ser69 residue in CaCRT is hydrogen-bonded with N6 of AcAc-CoA, in contrast to the corresponding Lys101 and Val74 residues in ECH and DmdD, and is involved in the stabilization of the adenine ring. Moreover, Ala24 of CaCRT is located near the phosphate moiety, whereas the corresponding Lys31 residue of DmdD is hydrogen-bonded with this moiety
metabolism
the enzyme is involved in benzoyl-coenzyme A degradation
metabolism
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the enzyme is involved in benzoyl-coenzyme A degradation
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homodimer
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2-enoyl-CoA hydratase 2 is the middle part of the MFP-2, the enzyme is a homodimer, unlike the mitochondrial 2-enoyl-CoA hydratase 1 that is a hexamer
additional information
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the CaCRT monomer consists of an N-terminal (NTD) and a C-terminal domains (CTD). The NTD (beta1-beta7 and alpha1-alpha9) harbors the canonical crotonase fold, where a large beta-sheet (beta1-beta4 and b6) is organized with a small beta-sheet (beta5 and beta7) forming two perpendicular beta-sheets. The CTD consists of three alpha-helices (alpha10-alpha12), and this domain mediates the oligomerization of CaCRT. Additionally, the extended alpha-helix (lphaa12) interacts with the NTD of a neighboring monomer and participates in the formation of its substrate binding site. The CTDs of six monomers participate mainly in the formation of the hexameric interface
hexamer
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a dimer of trimers
hexamer
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2-enoyl-CoA hydratase 2 is the middle part of the MFP-2, the enzyme is a homodimer, unlike the mitochondrial 2-enoyl-CoA hydratase 1 that is a hexamer
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purified recombinant His6-tagged enzyme in apo- and acetoacetyl-CoA bound forms, from precipitant solution containing 30% PEG 400, 0.1 M sodium cacodylate, pH 6.5, and 0.2 M lithium sulfate, 22°C, 5 days, X-ray diffraction structure determination and analysis at 2.0-2.2 A resolution, molecular replacement and modelling
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F143A
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site-directed mutagenesis, almost inactive mutant
F233A
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site-directed mutagenesis, almost inactive mutant
F82A
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site-directed mutagenesis, the mutant shows similar activity compared to wild-type enzyme
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recombinant C-terminally His6-tagged wild-type and mutant enzymes from Escherichia coli strain B834 by nickel affinity chromatography and gel filtration
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expressed in Ralstonia eutropha cells
expression in Escherichia coli
the CaCRT coding gene (Met1-Arg261) is amplified by PCR using the chromosomal DNA of Clostridium acetobutylicum strain ATCC 824 as a template, recombinant expression of C-terminally His6-tagged wild-type and mutant enzymes in Escherichia coli strain B834
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expressed in Ralstonia eutropha cells
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expressed in Ralstonia eutropha cells
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Moskowitz, G.J.; Merrick, J.M.
Metabolism of poly-beta-hydroxybutyrate. II. Enzymatic synthesis of D(-)-beta-hydroxybutyryl coenzyme A by an enoyl hydrase from Rhodospirillum rubrum
Biochemistry
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2748-2755
1969
Rhodospirillum rubrum
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Wu, L.; Liu, X.; Li, D.
Oct-2-yn-4-enoyl-CoA as a multifunctional enzyme inhibitor in fatty acid oxidation
Org. Lett.
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2235-2238
2008
Rattus norvegicus
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Budde, C.; Riedel, S.; Willis, L.; Rha, C.; Sinskey, A.
Production of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) from plant oil by engineered Ralstonia eutropha strains
Appl. Environ. Microbiol.
77
2847-2854
2011
Aeromonas caviae, Pseudomonas aeruginosa
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Schmid, G.; Rene, S.B.; Boll, M.
Enzymes of the benzoyl-coenzyme A degradation pathway in the hyperthermophilic archaeon Ferroglobus placidus
Environ. Microbiol.
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3289-3300
2015
Ferroglobus placidus (D3RXI4), Ferroglobus placidus DSM 10642 (D3RXI4)
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Kim, E.J.; Kim, Y.J.; Kim, K.J.
Structural insights into substrate specificity of crotonase from the n-butanol producing bacterium Clostridium acetobutylicum
Biochem. Biophys. Res. Commun.
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431-435
2014
Clostridium acetobutylicum
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