Information on EC 1.14.14.78 - phylloquinone omega-hydroxylase and Organism(s) Homo sapiens

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Homo sapiens


The taxonomic range for the selected organisms is: Homo sapiens

The enzyme appears in selected viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.14.78
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RECOMMENDED NAME
GeneOntology No.
phylloquinone omega-hydroxylase
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SYSTEMATIC NAME
IUBMB Comments
phylloquinone,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (omega-hydroxyphylloquinone forming)
A heme-thiolate protein (cytochrome P-450). Isolated from human tissue. The enzyme will also act on menaquinone-4. Prolonged action of CYP4F2, but not CYP4F11, on the omega hydroxyl group oxidizes it to the corresponding carboxylic acid. CYP4F2 also oxidizes leukotriene B4; see EC 1.14.13.30, leukotriene-B4 20-monooxygenase [1].
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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CYP4F2 is the principle leukotriene B4 omega-hydroxylating enzyme expressed in human liver and plays an important role in regulating circulating as well as hepatic levels of this powerful proinflammatory eicosanoid
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3-hydroxypalmitate + reduced NADPH-hemoprotein reductase] + O2
3,16-dihydroxypalmitate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
3-hydroxypalmitate + [reduced NADPH-hemoprotein reductase] + O2
3,16-dihydroxypalmitate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
3-hydroxystearate + [reduced NADPH-hemoprotein reductase] + O2
3,18-dihydroxystearate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2
(5Z,8Z,11Z,14Z)-20-hydroxyeicosatetraenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxyarachidonic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxyleukotriene B4 + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
menaquinone-4 + [reduced NADPH-hemoprotein reductase] + O2
omega-hydroxymenaquinone-4 + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
oleic acid + [reduced NADPH-hemoprotein reductase] + O2
18-hydroxyoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
palmitic acid + [reduced NADPH-hemoprotein reductase] + O2
16-hydroxypalmitic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
phylloquinone + [reduced NADPH-hemoprotein reductase] + O2
omega-hydroxyphylloquinone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
the enzyme exhibits tocopherol-omega-hydroxylase activity
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-
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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
menaquinone-4 + [reduced NADPH-hemoprotein reductase] + O2
omega-hydroxymenaquinone-4 + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
phylloquinone + [reduced NADPH-hemoprotein reductase] + O2
omega-hydroxyphylloquinone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
the enzyme exhibits tocopherol-omega-hydroxylase activity
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-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
-
contains Fe2+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
prostaglandin A1
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-
additional information
-
unaffected by lauric acid, palmitic acid, and prostaglandin F2alpha
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0564 - 0.074
3-hydroxypalmitate
0.055
3-hydroxystearate
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in 100 mM potassium phosphate buffer (pH 7.4), at 37C
0.0235 - 0.08
arachidonic acid
0.085
oleic acid
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at pH 7.4 and 37C
0.047
palmitic acid
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at pH 7.4 and 37C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.458
3-hydroxypalmitate
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at pH 7.4 and 37C
0.009
arachidonic acid
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at pH 7.4 and 37C
0.02
oleic acid
-
at pH 7.4 and 37C
0.03
palmitic acid
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at pH 7.4 and 37C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
6.17
3-hydroxypalmitate
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at pH 7.4 and 37C
0.12
arachidonic acid
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at pH 7.4 and 37C
0.2
oleic acid
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at pH 7.4 and 37C
0.63
palmitic acid
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at pH 7.4 and 37C
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50000
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x * 50000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 50000, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Ni2+-NTA agarose column chromatography, Biogel HTP hydroxylapatite column chromatography, and aminopropyl SPE column chromatography
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tryptamine CH-Sepharose column chromatography, DE-53 cellulose column chromatography, and Hypatite C column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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expressed in Escherichia coli BL21 cells
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
retinoic acid can regulate CYP4F2 gene activity with RXRalpha heterodimers stimulating while RARalpha functioning to repress CYP4F2 gene expression
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