Information on EC 1.14.18.4 - phosphatidylcholine 12-monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.18.4
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RECOMMENDED NAME
GeneOntology No.
phosphatidylcholine 12-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a 1-acyl-2-oleoyl-sn-glycero-3-phosphocholine + 2 ferrocytochrome b5 + O2 + 2 H+ = a 1-acyl-2-[(12R)-12-hydroxyoleoyl]-sn-glycero-3-phosphocholine + 2 ferricytochrome b5 + H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
hydroxylated fatty acid biosynthesis (plants)
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ricinoleate biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
1-acyl-2-oleoyl-sn-glycero-3-phosphocholine,ferrocytochrome-b5:oxygen oxidoreductase (12-hydroxylating)
The enzyme, characterized from the plant Ricinus communis (castor bean), is involved in production of the 12-hydroxylated fatty acid ricinoleate. The enzyme, which shares sequence similarity with fatty-acyl desaturases, requires a cytochrome b5 as the electron donor.
CAS REGISTRY NUMBER
COMMENTARY hide
77950-95-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene FAH12
UniProt
Manually annotated by BRENDA team
wild-type and OLE-1 mutant strain i.e. high-oleic castor mutant
SwissProt
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
1-acyl-2-oleoyl-sn-glycero-3-phosphocholine + ferrocytochrome b5 + O2
1-acyl-2-[(S)-12-hydroxyoleoyl]-sn-glycero-3-phosphocholine + ferricytochrome b5
show the reaction diagram
1-acyl-2-oleoyl-sn-glycero-3-phosphocholine + ferrocytochrome b5 + O2
1-acyl-2-[(S)-12-hydroxyoleoyl]-sn-glycero-3-phosphocholine + ferricytochrome b5 + H2O
show the reaction diagram
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?
a 1-acyl-2-oleoyl-sn-glycero-3-phosphocholine + 2 ferrocytochrome b5 + O2 + 2 H+
a 1-acyl-2-ricinoleoyl-sn-glycero-3-phosphocholine + 2 ferricytochrome b5 + H2O
show the reaction diagram
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?
a 1-acyl-2-oleoyl-sn-glycero-3-phosphoethanolamine + 2 ferrocytochrome b5 + O2 + 2 H+
a 1-acyl-2-ricinoleoyl-sn-glycero-3-phosphoethanolamine + 2 ferricytochrome b5 + H2O
show the reaction diagram
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?
cis-linoleic acid + reduced acceptor + O2
densipolic acid + acceptor + H2O
show the reaction diagram
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?
cis-oleic acid + reduced acceptor + O2
ricinoleic acid + acceptor + H2O
show the reaction diagram
eicosenoic acid + reduced acceptor + O2
lesquerolic acid + acceptor + H2O
show the reaction diagram
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?
linoleic acid + ferrocytochrome P-450 + O2
linolenic acid + ferricytochrome P-450 + H2O
show the reaction diagram
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?
oleate + ferrocytochrome P-450 + H+ + O2
12-hydroxy-oleate + ferricytochrome P-450 + H2O
show the reaction diagram
oleic acid + 2 ferrocytochrome b5 + O2 + 2 H+
ricinoleic acid + 2 ferricytochrome b5 + H2O
show the reaction diagram
oleic acid esterified to membrane lipid phosphatidylcholine + reduced acceptor + H+ + O2
hydroxy fatty acids in triacylglycerol + acceptor + H2O
show the reaction diagram
D2CPE1
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?
palmitoleate + ferrocytochrome P-450 + H+ + O2
12-hydroxypalmitoleate + ferricytochrome P-450 + H2O
show the reaction diagram
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?
additional information
?
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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
1-acyl-2-oleoyl-sn-glycero-3-phosphocholine + ferrocytochrome b5 + O2
1-acyl-2-[(S)-12-hydroxyoleoyl]-sn-glycero-3-phosphocholine + ferricytochrome b5
show the reaction diagram
1-acyl-2-oleoyl-sn-glycero-3-phosphocholine + ferrocytochrome b5 + O2
1-acyl-2-[(S)-12-hydroxyoleoyl]-sn-glycero-3-phosphocholine + ferricytochrome b5 + H2O
show the reaction diagram
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?
cis-oleic acid + reduced acceptor + O2
ricinoleic acid + acceptor + H2O
show the reaction diagram
oleate + ferrocytochrome P-450 + H+ + O2
12-hydroxy-oleate + ferricytochrome P-450 + H2O
show the reaction diagram
A5HB93
the enzyme is primarily a fatty acid hydroxylase, rather than a bifunctional oleate 12-hydroxylase-desaturase, involved in ricinoleic acid biosynthesis, overview
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?
oleic acid esterified to membrane lipid phosphatidylcholine + reduced acceptor + H+ + O2
hydroxy fatty acids in triacylglycerol + acceptor + H2O
show the reaction diagram
D2CPE1
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?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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no inhibition by KCN, CO and metapyrone
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
EDTA
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slight stimulation
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.004
O2
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
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assay at
7.2
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assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
44000
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x * 44000, deduced from gene sequence
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 44000, deduced from gene sequence
additional information
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
encoded enzyme has both hydroxylase and desaturase activities
expression in Arabidopsis thaliana
expression in Pichia pastoris
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expression in Schizosaccharomyces pombe
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FAH gene, unrooted phylogenetic analysis, functional expression in Saccharomyces cerevisiae, expression in transgenic Arabidopsis thaliana plants under control of a seed-specific promoter
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fatty acyl desaturase homolog
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gene FAH12, recombinant overexpression in Schizosaccharomyces pombe strain ARC010-1, RT-PCR enzyme expression analysis. The enzyme product is toxic for the cells. Gene plg7, encoding phospholipase A2, acts as a multicopy suppressor restoring the growth defect by removing ricinoleic acid from phospholipids and inducing secretion of a part of the released free ricinoleic acid into culture media
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gene FAH12, subcloning in Escherichia coli strain DH5alpha, expression in Saccharomyces cerevisiae results in the synthesis of ricinoleic acid and very low levels of di-unsaturated fatty acids. Expression of LlinFAH12 in Arabidopsis thaliana seeds results in hydroxy fatty acid accumulation, fatty acid composition in transformed compared to wild-type plants, overview
gene RcFAH12, DNA and amino acid sequence determination and analysis, sequence comparisons, quantitative real-time PCR enzyme expression analysis, recombinant expression of wild-type and mutant enzymes in Saccharomyces cerevisiae strain W303-1A, fatty acid analysis
PCR-amplification, plant transformation by heat shock transformation of Agrobacterium tumefaciens (GV3101) with vector, expression in EMS mutant or T-DNA insertion lines of Arabidopsis thaliana deficient in the production of the enzymes diacylglycerol acyltransferase-1 (DGAT1), phospholipid: diacylglycerol acyltransferase-1 (PDAT1) and the homologue of PDAT1 phospholipid: diacylglycerol acyltransferase-2 (PDAT2)
D2CPE1
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
M295L
site-directed mutagenesis, expression of the mutant FAH12gene in yeast does not result in any obvious changes in the ratio of hydroxy and diunsaturated fatty acids accumulating
F49S/V242A/H319Q
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis