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Information on EC 1.3.1.124 - 2,4-dienoyl-CoA reductase [(3E)-enoyl-CoA-producing]
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1.3.1.124 2,4-dienoyl-CoA reductase [(3E)-enoyl-CoA-producing]IUBMB Comments
This enzyme, characterized from eukaryotic organisms, catalyses the reduction of either (2E,4E)-2,4-dienoyl-CoA or (2E,4Z)-2,4-dienoyl-CoA to (3E)-3-enoyl-CoA. The best substrates for the enzyme from bovine liver have a chain-length of 8 or 10 carbons. Mammals possess both mitochondrial and peroxisomal variants of this enzyme. cf. EC 1.3.1.34, 2,4-dienoyl-CoA reductase [(2E)-enoyl-CoA-producing].
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Word Map
The enzyme appears in viruses and cellular organisms
Reaction Schemes
a (3E)-3-enoyl-CoA
+
=
+
+
a (3E)-3-enoyl-CoA
+
=
+
+
Synonyms
decr1, sps19, 4-enoyl-coa reductase, decr2, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2,4-dienoyl-CoA reductase
4-enoyl-CoA reductase
DECR
DECR1
DECR2
DELTA2,DELTA4-dienoyl-CoA reductase
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ambiguous
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SPS19
additional information
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enzyme belongs to the short-chain dehydrogenase/reductase family with a distinctive catalytic center
2,4-dienoyl-CoA reductase
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DECR1
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DECR2
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SPS19
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a (3E)-3-enoyl-CoA + NADP+ = a (2E,4E)-2,4-dienoyl-CoA + NADPH + H+
(1)
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a (3E)-3-enoyl-CoA + NADP+ = a (2E,4Z)-2,4-dienoyl-CoA + NADPH + H+
(2)
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a (2E)-2-enoyl-CoA + NADP+ = a (2E,4E)-2,4-dienoyl-CoA + NADPH + H+
reaction mechanism, E276 is the proton donor in catalysis
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a (2E)-2-enoyl-CoA + NADP+ = a (2E,4E)-2,4-dienoyl-CoA + NADPH + H+
reaction mechanism, enzyme-ligand interactions in a distinctive short-chain reductase active site, catalytic site structure, stabilization of the dienolate reaction intermediate by Tyr199 and Asn148, and NADP+, overview
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a (2E)-2-enoyl-CoA + NADP+ = a (2E,4E)-2,4-dienoyl-CoA + NADPH + H+
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PATHWAY SOURCE
PATHWAYS
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, , , ,
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SYSTEMATIC NAME
IUBMB Comments
(3E)-3-enoyl-CoA:NADP+ 4-oxidoreductase
This enzyme, characterized from eukaryotic organisms, catalyses the reduction of either (2E,4E)-2,4-dienoyl-CoA or (2E,4Z)-2,4-dienoyl-CoA to (3E)-3-enoyl-CoA. The best substrates for the enzyme from bovine liver have a chain-length of 8 or 10 carbons. Mammals possess both mitochondrial and peroxisomal variants of this enzyme. cf. EC 1.3.1.34, 2,4-dienoyl-CoA reductase [(2E)-enoyl-CoA-producing].
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,4E)-2,4-hexadienoyl-CoA + NADPH + H+
(3E)-3-hexenoyl-CoA + NADP+
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-
-
?
(2E,4E)-hexa-2,4-dienoyl-CoA + NADPH + H+
(3E)-hex-3-enoyl-CoA + NADP+
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-
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?
2,4,7,10,13,16,19-docosaheptaenoyl-CoA + NADPH
?
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assay contains additionally 0.06% Triton X-100
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?
2,4,7,10,13,16,19-docosaheptaenoyl-CoA + NADPH + H+
(3E)-3,7,10,13,16,19-docosahexaenoyl-CoA + NADP+
2-cis,4-cis/trans-dienoyl-CoA + NADPH + H+
3-trans-enoyl-CoA + NADP+
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-
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?
2-fluoro-trans-trans-2,4-octadienoyl-CoA + NADPH
2-fluoro-trans-3-octenoyl-CoA + NADP+
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substrate analogue, recombinant enzyme, reaction mechanism
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?
2-trans,4-cis-decadienoylcarnitine + ?
?
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abnormal unsaturated fatty acid oxidation
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?
5-methyl-trans-trans-2,4-hexadienoyl-CoA + NADPH
5-methyl-trans-3-hexenoyl-CoA + NADP+
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substrate analogue, recombinant enzyme
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?
5-phenyl-(2E,4E)-2,4-pentadienoyl-CoA + NADPH + H+
5-phenyl-(3E)-penta-3-enoyl-CoA + NADP+
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?
trans, trans-2,4-decadienoyl-CoA + NADPH + H+
trans-deca-3-enoyl-CoA + NADP+
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?
trans-2,3-didehydroacyl-CoA + NADP+
trans,trans-2,3,4,5-tetradehydroacyl-CoA + NADPH + H+
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-
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?
(2E,4E)-2,4-decadienoyl-CoA + NADPH + H+
(3E)-3-decaenoyl-CoA + NADP+
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-
-
-
?
(2E,4E)-2,4-decadienoyl-CoA + NADPH + H+
(3E)-3-decaenoyl-CoA + NADP+
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-
-
?
(2E,4E)-2,4-decadienoyl-CoA + NADPH + H+
(3E)-3-decaenoyl-CoA + NADP+
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-
-
-
?
(2E,4E)-2,4-decadienoyl-CoA + NADPH + H+
(3E)-deca-3-enoyl-CoA + NADP+
preferred substrate
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?
(2E,4E)-2,4-decadienoyl-CoA + NADPH + H+
(3E)-deca-3-enoyl-CoA + NADP+
preferred substrate
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?
(2E,4E)-2,4-decadienoyl-CoA + NADPH + H+
(3E)-deca-3-enoyl-CoA + NADP+
preferred substrate
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?
(2E,4E)-2,4-hexadienoyl-CoA + NADPH + H+
(3E)-hexa-3-enoyl-CoA + NADP+
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-
-
?
(2E,4E)-2,4-hexadienoyl-CoA + NADPH + H+
(3E)-hexa-3-enoyl-CoA + NADP+
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?
(2E,4E)-2,4-hexadienoyl-CoA + NADPH + H+
(3E)-hexa-3-enoyl-CoA + NADP+
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?
(2E,4E)-2,4-octadienoyl-CoA + NADPH + H+
(3E)-3-octaenoyl-CoA + NADP+
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-
?
(2E,4E)-2,4-octadienoyl-CoA + NADPH + H+
(3E)-3-octaenoyl-CoA + NADP+
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?
(2E,4Z)-2,4-decadienoyl-CoA + NADPH + H+
(3E)-3-decaenoyl-CoA + NADP+
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?
(2E,4Z)-2,4-decadienoyl-CoA + NADPH + H+
(3E)-3-decaenoyl-CoA + NADP+
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preferred over substrate (2E,4E)-2,4-decadienoyl-CoA
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?
2,4,7,10,13,16,19-docosaheptaenoyl-CoA + NADPH + H+
(3E)-3,7,10,13,16,19-docosahexaenoyl-CoA + NADP+
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?
2,4,7,10,13,16,19-docosaheptaenoyl-CoA + NADPH + H+
(3E)-3,7,10,13,16,19-docosahexaenoyl-CoA + NADP+
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?
2-trans,4-cis-decadienoyl-CoA + NADPH
3-trans-decenoyl-CoA + NADP+
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?
2-trans,4-cis-decadienoyl-CoA + NADPH
3-trans-decenoyl-CoA + NADP+
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stereochemistry not determined
?
2-trans,4-trans-decadienoyl-CoA + NADPH
3-decenoyl-CoA + NADP+
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?
trans-trans-2,4-hexadienoyl-CoA + NADPH
trans-3-hexenoyl-CoA + NADP+
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reaction mechanism
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?
trans-trans-2,4-hexadienoyl-CoA + NADPH
trans-3-hexenoyl-CoA + NADP+
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substrate binding mechanism and structure
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r
additional information
?
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the 3',5'-ADP moiety of 2,4-dienoyl-CoA thioesters contributes a substantial part to the binding of these compounds to 2,4-dienoyl-CoA reductases
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additional information
?
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enzyme is the key enzyme of beta-oxidation of unsaturated fatty acid in mitochondria and to a lesser extent in peroxisomes, three accessory proteins are involved in the pathway
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?
additional information
?
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key enzyme in the beta-oxidation of unsaturated fatty acids, naturally occuring lethal enzyme deficiency
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?
additional information
?
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2,4-dienoyl-CoA reductase as an auxiliary enzyme in the mitochondrial beta-oxidation of unsaturated fatty acids
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?
additional information
?
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DECR may also play a role in the degradation of fatty acids containing odd-numbered double bonds because the intermediate 2,5-dienoyl-CoA may be isomerized by enoyl-CoA isomerase to 3,5-dienoyl-CoA and then converted to 2,4-dienoyl-CoA by a specific delta3,5,delta2,4-dienoyl-CoA isomerase
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?
additional information
?
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in eukaryotes, double bonds in even-numbered positions are reduced by an NADPH-dependent 2,4-dienoyl-CoA reductase to 3-enoyl-CoA, which is then isomerized by enoyl-CoA isomerase to trans-2-enoyl-CoA, suitable for further oxidation
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?
additional information
?
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products are DELTA3-enoyl-CoAs but not Delta2-enoyl-CoAs
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,4E)-2,4-decadienoyl-CoA + NADPH + H+
(3E)-3-decaenoyl-CoA + NADP+
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?
(2E,4E)-2,4-octadienoyl-CoA + NADPH + H+
(3E)-3-octaenoyl-CoA + NADP+
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-
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?
(2E,4Z)-2,4-decadienoyl-CoA + NADPH + H+
(3E)-3-decaenoyl-CoA + NADP+
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preferred over substrate (2E,4E)-2,4-decadienoyl-CoA
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-
?
2-cis,4-cis/trans-dienoyl-CoA + NADPH + H+
3-trans-enoyl-CoA + NADP+
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-
?
2-trans,4-cis-decadienoylcarnitine + ?
?
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abnormal unsaturated fatty acid oxidation
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?
trans-2,3-didehydroacyl-CoA + NADP+
trans,trans-2,3,4,5-tetradehydroacyl-CoA + NADPH + H+
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?
additional information
?
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enzyme is the key enzyme of beta-oxidation of unsaturated fatty acid in mitochondria and to a lesser extent in peroxisomes, three accessory proteins are involved in the pathway
-
-
?
additional information
?
-
-
key enzyme in the beta-oxidation of unsaturated fatty acids, naturally occuring lethal enzyme deficiency
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-
?
additional information
?
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2,4-dienoyl-CoA reductase as an auxiliary enzyme in the mitochondrial beta-oxidation of unsaturated fatty acids
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-
?
additional information
?
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-
DECR may also play a role in the degradation of fatty acids containing odd-numbered double bonds because the intermediate 2,5-dienoyl-CoA may be isomerized by enoyl-CoA isomerase to 3,5-dienoyl-CoA and then converted to 2,4-dienoyl-CoA by a specific delta3,5,delta2,4-dienoyl-CoA isomerase
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-
?
additional information
?
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in eukaryotes, double bonds in even-numbered positions are reduced by an NADPH-dependent 2,4-dienoyl-CoA reductase to 3-enoyl-CoA, which is then isomerized by enoyl-CoA isomerase to trans-2-enoyl-CoA, suitable for further oxidation
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?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Clofibrate
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ethyl alpha-(p-chlorophenoxy)isobutyrate, activation ATP-stimulated
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Breast Neoplasms
Elevated expression of DecR1 impairs ErbB2/Neu-induced mammary tumor development.
Carcinogenesis
Elevated expression of DecR1 impairs ErbB2/Neu-induced mammary tumor development.
Neoplasm Metastasis
Human DECR1 is an androgen-repressed survival factor that regulates PUFA oxidation to protect prostate tumor cells from ferroptosis.
Neoplasms
2,4-dienoyl-CoA reductase regulates lipid homeostasis in treatment-resistant prostate cancer.
Neoplasms
Elevated expression of DecR1 impairs ErbB2/Neu-induced mammary tumor development.
Neoplasms
Human DECR1 is an androgen-repressed survival factor that regulates PUFA oxidation to protect prostate tumor cells from ferroptosis.
Non-alcoholic Fatty Liver Disease
Protein interaction mapping interpretation of none alcoholic fatty liver disease model of rats after fat diet feeding.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0065
2-fluoro-trans-trans-2,4-octadienoyl-CoA
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recombinant His-tagged truncated wild-type enzyme, pH 6.0, 22°C
0.016
5-methyl-trans-trans-2,4-hexadienoyl-CoA
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recombinant His-tagged truncated wild-type enzyme, pH 6.0, 22°C
0.102
2,4,7,10,13,16,19-docosaheptaenoyl-CoA
absence of albumin, pH 7.4, 30°C
0.0045
trans-trans-2,4-hexadienoyl-CoA
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recombinant His-tagged mutant D300A, pH 6.0, 22°C
0.014
trans-trans-2,4-hexadienoyl-CoA
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recombinant His-tagged truncated wild-type enzyme, pH 6.0, 22°C
0.041
trans-trans-2,4-hexadienoyl-CoA
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recombinant His-tagged mutant E227A, pH 6.0, 22°C
0.067
trans-trans-2,4-hexadienoyl-CoA
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recombinant His-tagged mutant E276A, pH 6.0, 22°C
0.154
trans-trans-2,4-hexadienoyl-CoA
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recombinant His-tagged mutant E154A, pH 6.0, 22°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.00281
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4-cis-decenoyl-CoA, NADPH, protein fraction virtually free of 2-enoyl-CoA reductase activity
0.00882
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2-trans,4-trans-hexadienoyl-CoA, NADPH, protein fraction virtually free of 2-enoyl-CoA reductase activity
0.0331
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trans-2-trans-4-hexedienoyl-CoA as a substrate, clofibrate-treated
0.0461
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pent-2,4-dienoyl-CoA, NADPH, fed partially hydrogenated marine oils
0.0605
-
hexa-2,4-dienoyl-CoA, NADPH, fed partially hydrogenated marine oils
0.0895
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pent-2,4-dienoyl-CoA, NADPH, fed partially hydrogenated marine oils
0.5
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reductase activity for wild-type and Decr-/- mice, the observed residual activity represents the activity of mitochondrial 2-enoyl thioester reductase, which functions in mitochondrial fatty acid synthesis and can also reduce 2,4-hexadienoyl-CoA in vitro
additional information
additional information
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analysis of liver fatty acids after the mice are fasted for 24 h indicates that fasting has a minor effect on the lipid content of wild type liver, with an overall increase of 29% in the concentration of fatty acids, in Decr-/- mice, the overall concentration of fatty acids increases by 108% after fasting
additional information
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Decr-/- mice show decreased blood glucose and elevated non-esterified fatty acids concentrations after fasting in comparison to wild type mice
additional information
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fasting increases the total concentration of acylcarnitines by 2fold in wild type mice (567 nM), in Decr-/- mice, a markedly higher 9fold increase is observed (2150 nM)
additional information
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immunoblotting of mitochondrial extracts from liver, muscle and heart with an antibody against human DECR reveals a detectable signal from wild type mice, whereas no signal can be detected for homozygous null mutant mice
additional information
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in Decr-/- mice, the overall concentration of fatty acids increases by 108% after fasting, the most profound changes between fasted wild type and Decr-/- mice are observed for the levels of palmitoleic acid (C16:1), oleic acid, linolenic acid (C18:3) and linoleic acid, which are 2.5- to 3.8fold higher in Decr-/- mice, in comparison to the fed state, the concentrations of monounsaturated fatty acids and polyunsaturated fatty acids increase by 288% and 254%, respectively
additional information
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mitochondrial 2,4-dienoyl-CoA reductase activity in mice is indispensable for the complete oxidation of (poly)unsaturated fatty acids and for adaptation to metabolic stress
additional information
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mitochondrial 2,4-dienoyl-CoA reductase deficiency in mice results in severe hypoglycemia with stress intolerance and unimpaired ketogenesis
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
source of the natural substrate 2-trans,4cis-decadienoylcarnitine
brenda
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brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE