Information on EC 4.2.1.152 - hydroperoxy icosatetraenoate dehydratase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
4.2.1.152
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RECOMMENDED NAME
GeneOntology No.
hydroperoxy icosatetraenoate dehydratase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a hydroperoxyicosatetraenoate = an oxoicosatetraenoate + H2O
show the reaction diagram
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SYSTEMATIC NAME
IUBMB Comments
hydroperoxyicosatetraenoate hydro-lyase (oxoicosatetraenoate-forming)
Binds Fe2+. The mammalian enzymes accept a range of hydroperoxyicosatetraenoates (HPETE). The human enzyme has highest activity with (12R)-HPETE, followed by (12S)-HPETE and (15R)-HPETE with much lower efficiency. The murine enzyme has highest activity with (8R)-HPETE followed by (8S)-HPETE. All HPETE isoforms are converted to the corresponding oxoicosatetraenoate forms (KETE) [2]. The enzymes also catalyse the reaction of EC 5.4.4.7, hydroperoxy icosatetraenoate isomerase.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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the enzyme contributes to epidermal differentiation
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(12R)-HPETE
(8R)-hydroxy-(11R,12R)-epoxyeicosa-(5Z,9E,14Z)-trienoic acid + H2O
show the reaction diagram
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preferred substrate
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?
(12R)-HPETE
?
show the reaction diagram
(12R)-hydroperoxyeicosatetraenoic acid
(8R)-hydroxy-(11R,12R)-epoxyeicosa-(5Z,9E,14Z)-trienoic acid + 12-oxoeicosatetraenoic acid
show the reaction diagram
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preferred substrate
2:1 ratio, 2:1 product ratio
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?
(12S)-HPETE
?
show the reaction diagram
(12S)-hydroperoxyeicosatetraenoic acid
(10R)-hydroxy-(11S,12S)-epoxyeicosa-(5Z,8Z,14Z)-trienoic acid + (8R)-hydroxy-(11S,12S)-epoxyeicosa-(5Z,9E,14Z)-trienoic acid + 12-oxoeicosatetraenoic acid
show the reaction diagram
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-
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?
(15S)-HPETE
(15S)HETE + H2O
show the reaction diagram
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-
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?
(15S)-HPETE
?
show the reaction diagram
(15S)-hydroperoxyeicosatetraenoic acid
(13R)-hydroxy-(14S,15S)-epoxyeicosa-(5Z,8Z,11Z)-trienoic acid + 12-oxoeicosatetraenoic acid
show the reaction diagram
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?
(5S)-HPETE
(7R)-hydroxy-(5S,6S)-epoxyeicosa-(8Z,11Z,14Z)-trienoic acid + H2O
show the reaction diagram
(5Z,8Z,10E,12R,14Z)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
(8R)-hydroxy-(11R,12R)-epoxyeicosa-(5Z,9E,14Z)-trienoate + H2O
show the reaction diagram
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(8R)-HPETE
?
show the reaction diagram
(8S)-HPETE
(10R)-hydroxy-(8S,9S)-epoxyeicosa-(5Z,11Z,14Z)-trienoic acid + H2O
show the reaction diagram
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?
(9E,11Z,14Z)-20:3omega6
(9S)-hydroperoxy-(10E,12E,14Z)-eicosatrienoic acid + H2O
show the reaction diagram
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good substrate
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-
?
arachidonic acid + O2
5-HPETE + 7-HPETE + 9-HPETE
show the reaction diagram
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in the absence of fatty acid hydroperoxides, the enzyme shows only weak and slow activity with arachidonic acid
22%, 25%, and 29% yield, respectively
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?
arachidonoyl-lysophosphatidic acid
15-HPETE-lysophosphatidic acid + 13-HPETE-lysophosphatidic acid + 11HPETE-lysophosphatidic acid + 5-HPETE-lysophosphatidic acid + H2O
show the reaction diagram
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36%, 22%, 21%, and 13% yield, respectively
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?
additional information
?
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linoleic, arachidonic, and eicosapentaenoic acids, the methyl esters of arachidonic acid and linoleic acid, arachidonyl phosphatidylcholine, anandamide, and the cholesteryl ester of arachidonic acid are no substrates
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(12R)-HPETE
(8R)-hydroxy-(11R,12R)-epoxyeicosa-(5Z,9E,14Z)-trienoic acid + H2O
show the reaction diagram
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preferred substrate
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?
(12R)-HPETE
?
show the reaction diagram
(12R)-hydroperoxyeicosatetraenoic acid
(8R)-hydroxy-(11R,12R)-epoxyeicosa-(5Z,9E,14Z)-trienoic acid + 12-oxoeicosatetraenoic acid
show the reaction diagram
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preferred substrate
2:1 ratio
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?
(12S)-HPETE
?
show the reaction diagram
(15S)-HPETE
(15S)HETE + H2O
show the reaction diagram
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-
-
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?
(15S)-HPETE
?
show the reaction diagram
(5S)-HPETE
(7R)-hydroxy-(5S,6S)-epoxyeicosa-(8Z,11Z,14Z)-trienoic acid + H2O
show the reaction diagram
(8R)-HPETE
?
show the reaction diagram
(8S)-HPETE
(10R)-hydroxy-(8S,9S)-epoxyeicosa-(5Z,11Z,14Z)-trienoic acid + H2O
show the reaction diagram
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?
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
nordihydroguaiaretic acid
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submicromolar concentrations of nordihydroguaiaretic acid cause a dose-dependent increase in reaction rate 83-4fold with 12R-HPETE and up to 6fold with 15S-HPETE
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(13S)-HPODE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Ni-NTA agarose column chromatography
Ni-NTA column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli and COS7 cells
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expressed in Escherichia coli BL21(DE3) cells
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A451G
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unlike wild type enzyme, the mutant reacts well with arachidonic acid even in the absence of fatty acid hydroperoxides, yet only after an unusually long lag phase of about 20 min
R396S
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inactive
V500F
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inactive