Information on EC 1.14.13.205 - long-chain fatty acid omega-monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.205
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RECOMMENDED NAME
GeneOntology No.
long-chain fatty acid omega-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a long-chain fatty acid + NADPH + H+ + O2 = an omega-hydroxy-long-chain fatty acid + NADP+ + H2O
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
cutin biosynthesis
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sophorolipid biosynthesis
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sporopollenin precursors biosynthesis
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suberin monomers biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
long-chain fatty acid,NADPH:O2 oxidoreductase (omega-hydroxylating)
The plant enzyme CYP704B1, which is involved in the synthesis of sporopollenin, a complex polymer found at the outer layer of spores and pollen, acts on palmitate (18:0), stearate (18:0) and oleate (18:1). The plant enzyme CYP86A1 also acts on laurate (12:0). The enzyme from the yeast Starmerella bombicola (CYP52M1) acts on C16 to C20 saturated and unsaturated fatty acids and can also hydroxylate the (omega-1) position. The mammalian enzyme CYP4A acts on laurate (12:0), myristate (14:0), palmitate (16:0), oleate (18:1), and arachidonate (20:4).
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
9,10-epoxystearic acid + NADPH + H+ + O2
18-hydroxy-9,10-epoxystearic acid + NADP+ + H2O
show the reaction diagram
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?
alpha-linolenic acid + NADPH + H+ + O2
18-hydroxylinolenic acid + NADP+ + H2O
show the reaction diagram
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?
arachidonic acid + NADPH + H+ + O2
20-hydroxyarachidonic acid + NADP+ + H2O
show the reaction diagram
isolauric acid + NADPH + H+ + O2
11-hydroxyisolauric acid + NADP+ + H2O
show the reaction diagram
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?
isomyristic acid + NADPH + H+ + O2
13-hydroxyisomyrisitc acid + NADP+ + H2O
show the reaction diagram
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?
lauric acid + NADPH + H+ + O2
12-hydroxylauric acid + NADP+ + H2O
show the reaction diagram
linoleic acid + NADPH + H+ + O2
18-hydroxylinoleic acid + NADP+ + H2O
show the reaction diagram
linolenic acid + NADPH + H+ + O2
18-hydroxlinolenic acid + NADP+ + H2O
show the reaction diagram
best substrate
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?
myristic acid + NADPH + H+ + O2
14-hydroxymyrisitic acid + NADP+ + H2O
show the reaction diagram
myristic acid + NADPH + H+ + O2
14-hydroxymyristic acid + NADP+ + H2O
show the reaction diagram
oleic acid + NADPH + H+ + O2
18-hydroxyoleic acid + NADP+ + H2O
show the reaction diagram
palmitic acid + NADPH + H+ + O2
16-hydroxypalmitic acid + NADP+ + H2O
show the reaction diagram
palmitic acid + NADPH + H+ + O2
18-hydroxypalmitic acid + NADP+ + H2O
show the reaction diagram
palmitoleic acid + NADPH + H+ + O2
18-hydroxypalmitoleic acid + NADP+ + H2O
show the reaction diagram
tridecanoic acid + NADPH + H+ + O2
13-hydroxytridecanoic acid + NADP+ + H2O
show the reaction diagram
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?
undecanoic acid + NADPH + H+ + O2
11-hydroxyundecanoic acid + NADP+ + H2O
show the reaction diagram
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?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
26% of the activity with NADPH
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.003 - 0.054
arachidonic acid
0.022 - 0.08
lauric acid
0.068
linoleic acid
pH 7.0, 30°C
0.004 - 0.07
myristic acid
0.018 - 0.136
oleic acid
0.096
palmitic acid
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27°C, pH not specified in the publication
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01 - 0.1
arachidonic acid
0.58 - 10.8
lauric acid
0.1 - 3.8
myristic acid
0.01 - 0.02
oleic acid
0.002 - 1
palmitic acid
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.7
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substrate undecanoic acid, omega-1-hydroxylation, in nmol/min/nmol, pH 7.5, 37°C
1
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substrate lauric acid, omega-1-hydroxylation, in nmol/min/nmol, pH 7.5, 37°C
3
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substrate tridecanoic acid, omega-1-hydroxylation, in nmol/min/nmol, pH 7.5, 37°C
8.5
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substrate tridecanoic acid, omega-hydroxylation, in nmol/min/nmol, pH 7.5, 37°C
12
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substrate undecanoic acid, omega-hydroxylation, in nmol/min/nmol, pH 7.5, 37°C
13.9
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substrate isomyristic acid, omega-hydroxylation, in nmol/min/nmol, pH 7.5, 37°C
14.8
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substrate lauric acid, omega-hydroxylation, in nmol/min/nmol, pH 7.5, 37°C
24.5
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substrate isolauric acid, omega-hydroxylation, in nmol/min/nmol, pH 7.5, 37°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
CYP704B1 is expressed in the developing anthers
Manually annotated by BRENDA team
; CYP86A2 transcripts are 2- to 10fold less abundant in seedling roots, mature roots, and flower; CYP86A8 transcripts are 2fold more abundant in flowers than in seedling shoots; highest expression
Manually annotated by BRENDA team
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cultured hepatocyte
Manually annotated by BRENDA team
CYP86A2 transcripts are 2- to 10fold less abundant in seedling roots, mature roots, and flower; isoform CYP86A1 transcripts are 20fold more abundant in mature roots than in seedling roots
Manually annotated by BRENDA team
older rosettes, low expression
Manually annotated by BRENDA team
abundant expression in seedling shoots; isoform CYP86A1, transcripts are 17fold more abundant in seedling roots than in seedling shoots; shoot and root, low expression
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
52000
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x * 52000, SDS-PAGE, x * 59347, calculated
59347
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x * 52000, SDS-PAGE, x * 59347, calculated
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 52000, SDS-PAGE, x * 59347, calculated
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
construction of active site model. Hydrophobicity in the heme binding site is very different between active and inactive isoforms. CYP94C1 contains highly hydrophobic residues while inactive isoforms CYP704A2 and CYP711A1 do not
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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expression in Escherichia coli; expression in Escherichia coli; expression in Escherichia coli; expression in Escherichia coli
expression in Saccharomyces cerevisiae
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expression in Saccharomyces cerevisiae strain WAT11
expression in yeast WAT11 cells
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
CYP704B1 is highly coexpressed with CYP703A2, a cytochrome P450 involved in exine production
CYP86A1 transcripts are repressed 2.4fold by 27h of iodoacetc acid treatment and5.9fold by 27 h of salicylic acid treatment; CYP86A4 transcripts are repressed 9.0fold by short-term treatment with 1-aminocyclopropane-1-carboxylic acid and induced 1.9fold by long-term treatment with 1-aminocyclopropane-1-carboxylic acid. CYP86A4 transcripts are repressed 3.6fold by 3 h of wounding and 2.4fold in etiolated seedlings; CYP86A7 transcripts are significantly repressed by 2 h of drought treatment, 3 h of salicylic acid and wounding treatments, 3 and 27 h of 1-aminocyclopropane-1-carboxylic acid and mannitol treatments, and in both etiolated and dark-adapted seedlings; CYP86A8 transcripts are repressed by 30 min of wounding
CYP86A2 transcripts are transiently induced 2.5fold by 3 h of wounding and abscisic acid treatment, 2.3fold by 3 h of mannitol treatment, 1.7fold by 3 h of iodoacetic acid treatment, 1.6fold by 3 h of clofibrate treatment, more continuously induced 2.0- and 1.9fold by 30 and 120 min of drought treatment, and induced 1.9- to 2.3fold in etiolated and dark-adapted seedlings; CYP86A4 transcripts are induced 1.9fold by long-term treatment with 1-aminocyclopropane-1-carboxylic acid and repressed 9.0fold by short-term treatment with 1-aminocyclopropane-1-carboxylic acid; CYP86A7 transcripts are transiently induced 1.9fold by 3 h of clofibrate treatment, more continuously induced 1.6 and 1.5fold by 3 and 27 h of methyl jasmonate treatment, and slowly induced 1.7fold by 27 h abscisic acid treatment; CYP86A8 transcripts are induced by 3-h iodoacetic acid and abscisic acid treatments
in ciprofibrate-treated cells, CYP4A expression increases by 1.5- to 1.8fold
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isoform CYP52M1 is clearly upregulated during sophorolipid synthesis
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
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specific inhibition of either the CYP2C epoxygenase or the CYP4A omega-hydroxylase abrogates peroxisomal proliferation induced by the hypolipidemic drug cirpofibrate