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Information on EC 5.3.3.8 - DELTA3-DELTA2-enoyl-CoA isomerase
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5.3.3.8 DELTA3-DELTA2-enoyl-CoA isomeraseIUBMB Comments
The enzyme participates in the beta-oxidation of fatty acids with double bonds at an odd position. Processing of these substrates via the beta-oxidation system results in intermediates with a cis- or trans-double bond at position C3, which cannot be processed further by the regular enzymes of the beta-oxidation system. This enzyme isomerizes the bond to a trans bond at position C2, which can be processed further. The reaction rate is ten times higher for the (3Z) isomers than for (3E) isomers. The enzyme can also catalyse the isomerization of 3-acetylenic fatty acyl thioesters to 2,3-dienoyl fatty acyl thioesters.
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Word Map
- 5.3.3.8
-
beta-oxidation
- peroxisomal
- unsaturated
-
hydratase
-
auxiliary
-
2,4-dienoyl-coa
-
isomerization
-
oleic
-
odd-numbered
- 3-ketoacyl-coa
- crotonase
-
trifunctional
-
thiolase
-
protic
- d-3-hydroxyacyl-coa
-
4.2.1.17
-
1.3.1.34
- medicine
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
eci1p, delta3,delta2-enoyl-coa isomerase, 3,2-trans-enoyl-coa isomerase, ateci3, ateci2, delta3-delta2-enoyl-coa isomerase, 3-cis-2-trans-enoyl-coa isomerase, 2,3-enoyl-coa isomerase, 3-2trans-enoyl-coa isomerase, d3,d2-enoyl-coa isomerase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2,3-Enoyl-CoA isomerase
-
-
-
-
3,2-trans-Enoyl-CoA isomerase
3-2trans-Enoyl-CoA isomerase
-
-
-
-
3-cis-2-trans-Enoyl-CoA isomerase
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-
-
-
Acetylene-allene isomerase
-
-
-
-
D3,D2-enoyl-CoA isomerase
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-
-
-
DCI
DELTA3,DELTA2-enoyl-CoA isomerase
DELTA3-cis,DELTA2-trans-Enoyl-CoA isomerase
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-
-
-
DELTA3-cis-DELTA2-trans-enoyl-CoA isomerase
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-
-
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dodecenoyl coenzyme A DELTA isomerase
Dodecenoyl-CoA delta-isomerase
-
-
-
-
dodecenoyl-CoA DELTA3-cis-DELTA2-trans-isomerase
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-
-
-
ECI
ECI1
Eci1p
ECI2
Eci3
Hepatocellular carcinoma-associated antigen 88
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-
-
-
Isomerase, dodecenoyl coenzyme A Delta-
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-
-
-
Long-chain DELTA3,DELTA2-enoyl-CoA isomerase
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-
-
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PECI
Short chain DELTA3,DELTA2-enoyl-CoA isomerase
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-
-
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3,2-trans-Enoyl-CoA isomerase
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-
-
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DELTA3,DELTA2-enoyl-CoA isomerase
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-
-
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ECI
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a (3E)-alk-3-enoyl-CoA = a (2E)-alk-2-enoyl-CoA
(2)
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-
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a (3Z)-alk-3-enoyl-CoA = a (2E)-alk-2-enoyl-CoA
(1)
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
intramolecular oxidoreduction
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-
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isomerization
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-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
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, , , , , , , lipid metabolism, lipid metabolism, lipid metabolism, lipid metabolism
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SYSTEMATIC NAME
IUBMB Comments
(3Z/3E)-alk-3-enoyl-CoA (2E)-isomerase
The enzyme participates in the beta-oxidation of fatty acids with double bonds at an odd position. Processing of these substrates via the beta-oxidation system results in intermediates with a cis- or trans-double bond at position C3, which cannot be processed further by the regular enzymes of the beta-oxidation system. This enzyme isomerizes the bond to a trans bond at position C2, which can be processed further. The reaction rate is ten times higher for the (3Z) isomers than for (3E) isomers. The enzyme can also catalyse the isomerization of 3-acetylenic fatty acyl thioesters to 2,3-dienoyl fatty acyl thioesters.
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CAS REGISTRY NUMBER
COMMENTARY
62213-29-0
-
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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
(3E)-undecenoyl CoA
(2E)-undecenoyl CoA
-
intermediate of beta-oxidation of (10Z)-heptadecenoic acid. In vivo enzyme activity tests of the proteins encoded by AtECI1, AtECI2, and AtECI3 by complementation of the Saccharomyces cerevisiae double mutant eciDELTAdci1DELTA with deletions of the genes, DELTA2,DELTA3-enoyl-CoA isomerase and DELTA3,4,DELTA2,4-dienoyl CoA isomerase
-
-
?
(3E,7Z)-tridecedienoyl CoA
(2E,7Z)-tridecedienoyl CoA
-
intermediate of beta-oxidation of 10Z-heptadecenoic acid. In vivo enzyme activity tests of the proteins encoded by AtECI1, AtECI2, and AtECI3 by complementation of the Saccharomyces cerevisiae double mutant eciDELTAdci1DELTA with deletions of the genes, DELTA2,DELTA3-enoyl-CoA isomerase and DELTA3,4,DELTA2,4-dienoyl CoA isomerase
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-
?
2-trans,5-cis-tetradecadienoyl-CoA
3-cis,5-cis-tetradecadienoyl-CoA
-
-
-
?
trans-2-hexenoyl-CoA + H2O
3-hydroxyhexanoyl-CoA
K242C mutation allows Delta3-Delta2-enoyl-CoA isomerase to acquire enoyl-CoA hydratase activity
-
-
?
(3Z)-nonenoyl CoA
(2Z)-nonenoyl CoA
-
intermediate of beta-oxidation of (10Z)-heptadecenoic acid. In vivo enzyme activity tests of the proteins encoded by AtECI1, AtECI2, and AtECI3 by complementation of the Saccharomyces cerevisiae double mutant eciDELTAdci1DELTA with deletions of the genes, DELTA2,DELTA3-enoyl-CoA isomerase and DELTA3,4,DELTA2,4-dienoyl CoA isomerase
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-
?
2-trans,5-cis-tetradecadienoyl-CoA
3,5-cis-tetradecadienoyl-CoA
Escherichia coli B / ATCC 11303
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-
-
-
?
3-trans-Decenoyl-CoA
2-trans-Decenoyl-CoA
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42% of the activity relative to 3-cis-hexenoyl-CoA
-
-
?
3-trans-dodecenoyl-CoA
2-trans-dodecenoyl-CoA
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89% of the activity relative to 3-cis-hexenoyl-CoA
-
-
?
3-trans-Hexenoyl-CoA
2-trans-Hexenoyl-CoA
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2.8% of the activity relative to 3-cis-hexenoyl-CoA
-
-
?
3-trans-octenoyl-CoA
2-trans-octenoyl-CoA
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40% of the activity relative to 3-cis-hexenoyl-CoA
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-
?
additional information
?
-
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enzyme participates in the degradation of unsaturated fatty acids through beta-oxidation
-
-
?
additional information
?
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oleate is mostly (about 90%) degraded via beta-oxidation in Escherichia coli. A small amount of 2-trans,5-cis-tetradecadienoyl-CoA is diverted from the pathway via conversion to 3,5-cis-tetradecadienoyl-CoA by DELTA3,DELTA2-enoyl-CoA isomerase. The CoA-bound intermediate, which would strongly inhibit beta-oxidation if allowed to accumulate, is hydrolyzed and the resultant 3,5-tetradecadienoate is excreted into the growth medium.
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-
?
additional information
?
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Escherichia coli B / ATCC 11303
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oleate is mostly (about 90%) degraded via beta-oxidation in Escherichia coli. A small amount of 2-trans,5-cis-tetradecadienoyl-CoA is diverted from the pathway via conversion to 3,5-cis-tetradecadienoyl-CoA by DELTA3,DELTA2-enoyl-CoA isomerase. The CoA-bound intermediate, which would strongly inhibit beta-oxidation if allowed to accumulate, is hydrolyzed and the resultant 3,5-tetradecadienoate is excreted into the growth medium.
-
-
?
additional information
?
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the velocity ratios with 3-trans-C6:C10:C12-enoyl-CoA is 1:2.1:1.2 for the liver enzyme and 1:3.4:2.3 for the heart enzyme
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-
?
additional information
?
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the enzyme is essential for unsaturated fatty acid metabolism
-
?
additional information
?
-
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involved in mitochondrial beta-oxidation of unsaturated fatty acids. Decreased levels of this enzyme in metastatic breast cancer cells might have impact on the aberrant behavior of cancer cells
-
-
?
additional information
?
-
involved in mitochondrial beta-oxidation of unsaturated fatty acids. Decreased levels of this enzyme in metastatic breast cancer cells might have impact on the aberrant behavior of cancer cells
-
-
?
additional information
?
-
catalyzes the transformation of 3-cis- and 3-trans-enoyl-CoA esters arising during the stepwise degradation of cis-, mono-, and polyunsaturated fatty acids to the 2-trans-enoyl-CoA intermediates
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-
?
additional information
?
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catalyzes the transformation of 3-cis- and 3-trans-enoyl-CoA esters arising during the stepwise degradation of cis-, mono-, and polyunsaturated fatty acids to the 2-trans-enoyl-CoA intermediates
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-
?
additional information
?
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enzyme is important for the degradation of unsaturated fatty acids in the beta-oxidation system
-
-
?
additional information
?
-
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the enzyme is essential for unsaturated fatty acid metabolism
-
?
additional information
?
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in addition to the peroxisomal trifunctional enzyme and the mitochondrial enzyme which shows a preference for short-chain substrates, a separate isomerase with a preference for C10-C12 substrates is observed
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-
?
additional information
?
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no specificity for DELTA3-cis-enoyl-CoA esters of chain length between C6 and C16
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?
additional information
?
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MECI is most active in catalyzing the 3-cis/2-trans isomerization, ECI has a preference for the 3-trans/2-trans isomerization, and MFE1 is the optimal isomerase for the 2,5-/3,5-isomerization. 3-cis/2-trans and 2,5/3,5 isomerization in mitochondria are catalyzed overwhelmingly by MECI, whereas ECI contributes significantly to the 3-trans/2-trans isomerization. In peroxisomes, ECI is predicted to be the dominant enzyme for the 3-cis/2-trans and 3-trans/2-trans isomerization of long chain intermediates
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?
additional information
?
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key enzyme in mitochondrial beta-oxidation of unsaturated fatty acids
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-
?
additional information
?
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enzyme is responsible for the positional and geometric isomerization of beta,gamma-unsaturated fatty acyl-CoA intermediates arising during beta-oxidation of unsaturated long-chain fatty acids
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?
additional information
?
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mitochondrial enzyme is markedly induced by peroxisome proliferators, di-(2-ethylhexyl)phthalate and clofibrate
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-
?
additional information
?
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enzyme is important for the degradation of unsaturated fatty acids in the beta-oxidation system
-
-
?
additional information
?
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enzyme is important for the degradation of unsaturated fatty acids in the beta-oxidation system
-
-
?
additional information
?
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key enzyme in the degradation of unsaturated fatty acids
-
-
?
additional information
?
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involved in the enzymatic degradation of the cis-olefinic system of monounsaturated and polyunsaturated fatty acids
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-
?
additional information
?
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-
auxiliary enzyme that is essential for the operation of the major pathway of oleate beta-oxidation
-
?
additional information
?
-
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key enzyme for the beta-oxidation of unsaturated fatty acids
-
?
additional information
?
-
the enzyme is involved in beta-oxidation of unsaturated fatty acids
-
?
additional information
?
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-
one of the key enzymes involved in fatty acid oxidation
-
-
?
additional information
?
-
one of the key enzymes involved in fatty acid oxidation
-
-
?
additional information
?
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-
only one catalytic base, Glu158, is involved in shuttling the proton from the C2 carbon atom of the substrate, DELTA3-enol-CoA, to the C4 atom of the product DELTA2-enoyl-CoA
-
?
additional information
?
-
-
auxiliary enzyme required for beta-oxidation of unsaturated fatty acids
-
?
additional information
?
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the enzyme is essential for the beta-oxidation of unsaturated fatty acids
-
?
additional information
?
-
-
the enzyme is essential for the beta-oxidation of unsaturated fatty acids
-
?
additional information
?
-
-
main pathway for 9-cis,11-trans-octadecadienoic acid degradation requires the participation of DELTA3,DELTA2-enoyl-CoA isomerase
-
-
?
additional information
?
-
-
the synthesis of polyhydroxyalkanoate in cells grown in media containing 10-cis-heptadecenoic acid is dependent on the presence of DELTA3,DELTA2-enoyl-CoA isomerase activity. Degradation of 10-trans-heptadecenoic acid through beta-oxidation is severly reduced in mutants devoid of DELTA3,DELTA2-enoyl-CoA isomerase. The synthesis of the intermediate 3-trans-enoyl-CoA in the absence of the DELTA3,DELTA2-enoyl-CoA isomerase leads to the blockage of the direct multifunctional enzyme dependent pathway in vivo
-
-
?
additional information
?
-
-
the peroxisomal protein Yor180Cp associates with the enzyme in vivo
-
-
?
additional information
?
-
-
the synthesis of polyhydroxyalkanoate in cells grown in media containing 10-cis-heptadecenoic acid is dependent on the presence of DELTA3,DELTA2-enoyl-CoA isomerase activity. Degradation of 10-trans-heptadecenoic acid through beta-oxidation is severly reduced in mutants devoid of DELTA3,DELTA2-enoyl-CoA isomerase. The synthesis of the intermediate 3-trans-enoyl-CoA in the absence of the DELTA3,DELTA2-enoyl-CoA isomerase leads to the blockage of the direct multifunctional enzyme dependent pathway in vivo
-
-
?
additional information
?
-
-
main pathway for 9-cis,11-trans-octadecadienoic acid degradation requires the participation of DELTA3,DELTA2-enoyl-CoA isomerase
-
-
?
additional information
?
-
Saccharomyces cerevisiae BY4733
-
the peroxisomal protein Yor180Cp associates with the enzyme in vivo
-
-
?
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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
additional information
?
-
-
enzyme participates in the degradation of unsaturated fatty acids through beta-oxidation
-
-
?
additional information
?
-
-
oleate is mostly (about 90%) degraded via beta-oxidation in Escherichia coli. A small amount of 2-trans,5-cis-tetradecadienoyl-CoA is diverted from the pathway via conversion to 3,5-cis-tetradecadienoyl-CoA by DELTA3,DELTA2-enoyl-CoA isomerase. The CoA-bound intermediate, which would strongly inhibit beta-oxidation if allowed to accumulate, is hydrolyzed and the resultant 3,5-tetradecadienoate is excreted into the growth medium.
-
-
?
additional information
?
-
Escherichia coli B / ATCC 11303
-
oleate is mostly (about 90%) degraded via beta-oxidation in Escherichia coli. A small amount of 2-trans,5-cis-tetradecadienoyl-CoA is diverted from the pathway via conversion to 3,5-cis-tetradecadienoyl-CoA by DELTA3,DELTA2-enoyl-CoA isomerase. The CoA-bound intermediate, which would strongly inhibit beta-oxidation if allowed to accumulate, is hydrolyzed and the resultant 3,5-tetradecadienoate is excreted into the growth medium.
-
-
?
additional information
?
-
-
the enzyme is essential for unsaturated fatty acid metabolism
-
?
additional information
?
-
-
involved in mitochondrial beta-oxidation of unsaturated fatty acids. Decreased levels of this enzyme in metastatic breast cancer cells might have impact on the aberrant behavior of cancer cells
-
-
?
additional information
?
-
involved in mitochondrial beta-oxidation of unsaturated fatty acids. Decreased levels of this enzyme in metastatic breast cancer cells might have impact on the aberrant behavior of cancer cells
-
-
?
additional information
?
-
catalyzes the transformation of 3-cis- and 3-trans-enoyl-CoA esters arising during the stepwise degradation of cis-, mono-, and polyunsaturated fatty acids to the 2-trans-enoyl-CoA intermediates
-
-
?
additional information
?
-
-
catalyzes the transformation of 3-cis- and 3-trans-enoyl-CoA esters arising during the stepwise degradation of cis-, mono-, and polyunsaturated fatty acids to the 2-trans-enoyl-CoA intermediates
-
-
?
additional information
?
-
-
enzyme is important for the degradation of unsaturated fatty acids in the beta-oxidation system
-
-
?
additional information
?
-
-
the enzyme is essential for unsaturated fatty acid metabolism
-
?
additional information
?
-
-
key enzyme in mitochondrial beta-oxidation of unsaturated fatty acids
-
-
?
additional information
?
-
-
enzyme is responsible for the positional and geometric isomerization of beta,gamma-unsaturated fatty acyl-CoA intermediates arising during beta-oxidation of unsaturated long-chain fatty acids
-
-
?
additional information
?
-
-
mitochondrial enzyme is markedly induced by peroxisome proliferators, di-(2-ethylhexyl)phthalate and clofibrate
-
-
?
additional information
?
-
-
enzyme is important for the degradation of unsaturated fatty acids in the beta-oxidation system
-
-
?
additional information
?
-
-
enzyme is important for the degradation of unsaturated fatty acids in the beta-oxidation system
-
-
?
additional information
?
-
-
key enzyme in the degradation of unsaturated fatty acids
-
-
?
additional information
?
-
-
involved in the enzymatic degradation of the cis-olefinic system of monounsaturated and polyunsaturated fatty acids
-
-
?
additional information
?
-
-
auxiliary enzyme that is essential for the operation of the major pathway of oleate beta-oxidation
-
?
additional information
?
-
-
key enzyme for the beta-oxidation of unsaturated fatty acids
-
?
additional information
?
-
the enzyme is involved in beta-oxidation of unsaturated fatty acids
-
?
additional information
?
-
-
one of the key enzymes involved in fatty acid oxidation
-
-
?
additional information
?
-
one of the key enzymes involved in fatty acid oxidation
-
-
?
additional information
?
-
-
auxiliary enzyme required for beta-oxidation of unsaturated fatty acids
-
?
additional information
?
-
the enzyme is essential for the beta-oxidation of unsaturated fatty acids
-
?
additional information
?
-
-
the enzyme is essential for the beta-oxidation of unsaturated fatty acids
-
?
additional information
?
-
-
main pathway for 9-cis,11-trans-octadecadienoic acid degradation requires the participation of DELTA3,DELTA2-enoyl-CoA isomerase
-
-
?
additional information
?
-
-
the synthesis of polyhydroxyalkanoate in cells grown in media containing 10-cis-heptadecenoic acid is dependent on the presence of DELTA3,DELTA2-enoyl-CoA isomerase activity. Degradation of 10-trans-heptadecenoic acid through beta-oxidation is severly reduced in mutants devoid of DELTA3,DELTA2-enoyl-CoA isomerase. The synthesis of the intermediate 3-trans-enoyl-CoA in the absence of the DELTA3,DELTA2-enoyl-CoA isomerase leads to the blockage of the direct multifunctional enzyme dependent pathway in vivo
-
-
?
additional information
?
-
-
the synthesis of polyhydroxyalkanoate in cells grown in media containing 10-cis-heptadecenoic acid is dependent on the presence of DELTA3,DELTA2-enoyl-CoA isomerase activity. Degradation of 10-trans-heptadecenoic acid through beta-oxidation is severly reduced in mutants devoid of DELTA3,DELTA2-enoyl-CoA isomerase. The synthesis of the intermediate 3-trans-enoyl-CoA in the absence of the DELTA3,DELTA2-enoyl-CoA isomerase leads to the blockage of the direct multifunctional enzyme dependent pathway in vivo
-
-
?
additional information
?
-
-
main pathway for 9-cis,11-trans-octadecadienoic acid degradation requires the participation of DELTA3,DELTA2-enoyl-CoA isomerase
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Acquired Immunodeficiency Syndrome
Genetic variants in nuclear-encoded mitochondrial genes influence AIDS progression.
Hepatitis C
Systems virology identifies a mitochondrial fatty acid oxidation enzyme, dodecenoyl coenzyme A delta isomerase, required for hepatitis C virus replication and likely pathogenesis.
Infections
Systems virology identifies a mitochondrial fatty acid oxidation enzyme, dodecenoyl coenzyme A delta isomerase, required for hepatitis C virus replication and likely pathogenesis.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.17