Information on EC 2.7.8.1 - ethanolaminephosphotransferase

for references in articles please use BRENDA:EC2.7.8.1
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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.7.8.1
-
RECOMMENDED NAME
GeneOntology No.
ethanolaminephosphotransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
CDP-ethanolamine + 1,2-diacyl-sn-glycerol = CMP + a phosphatidylethanolamine
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
substituted phospho group transfer
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
phosphatidylethanolamine biosynthesis II
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plasmalogen biosynthesis
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phosphatidylethanolamine bioynthesis
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Phosphonate and phosphinate metabolism
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Glycerophospholipid metabolism
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Ether lipid metabolism
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Metabolic pathways
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
CDP-ethanolamine:1,2-diacyl-sn-glycerol ethanolaminephosphotransferase
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CAS REGISTRY NUMBER
COMMENTARY hide
9026-19-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
dual-specificity enzyme, activities of EC 2.7.8.1 and EC 2.7.8.2
SwissProt
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
the enzyme belongs to the CEPT subfamily
malfunction
reduction of phosphatidylcholine, e.g. by bacterial infection, results in apoptosis
metabolism
the CDP-choline and CDP-ethanolamine pathways are separate routes of phospholipid biosynthesis in mammalian cells, although the CEPT is probably a participant in both pathways. Physiological role of the CDP-choline pathway, overview
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
CDP-choline + 1,2-diacyl-sn-glycerol
CMP + a phosphatidylcholine
show the reaction diagram
-
-
-
r
CDP-choline + 1,2-diacylglycerol
CMP + phosphatidylcholine
show the reaction diagram
CDP-choline + diacylglycerol
phosphatidylcholine + CMP
show the reaction diagram
only at CDP-choline concentrations higher than 25 micromolar, pH 8, 10 min, 37°C, in presence of 0.0002% Tween 20, 1 mM EGTA, 5 mM MnCl2
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-
?
CDP-dimethylethanolamine + 1,2-diacylglycerol
CMP + phosphatidyldimethylethanolamine
show the reaction diagram
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enzyme form Cpt1p
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-
?
CDP-ethanolamine + 1,2-diacyl-sn-glycerol
CMP + a phosphatidylethanolamine
show the reaction diagram
CDP-ethanolamine + 1,2-diacylglycerol
CMP + a phosphatidylethanolamine
show the reaction diagram
CDP-ethanolamine + 1,2-dioleoylglycerol
CMP + dioleoylphosphatidylethanolamine
show the reaction diagram
CDP-ethanolamine + 1-alkyl-2-acyl-sn-glycerol
CMP + 1-alkyl-2-acyl-sn-glycero-3-phosphorylethanolamine
show the reaction diagram
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-
-
?
CDP-ethanolamine + 1-heptadecanoylglycerol
CMP + ?
show the reaction diagram
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-
-
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?
CDP-ethanolamine + 1-O-alk-1'-enyl-2-acyl-sn-glycerol
CMP + 1-O-alk-1'-enyl-2-acyl-sn-glycerol-3-phosphorylethanolamine
show the reaction diagram
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-
-
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?
CDP-ethanolamine + 1-oleoyl-2-lauroylglycerol
CMP + 1-oleoyl-2-lauroylphosphatidylethanolamine
show the reaction diagram
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-
-
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?
CDP-ethanolamine + 1-oleoyl-2-palmitoylglycerol
CMP + 1-oleoyl-2-palmitoylphosphatidylethanolamine
show the reaction diagram
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-
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?
CDP-ethanolamine + 1-oleoyl-2-stearoyl-sn-glycerol
CMP + 1-oleoyl-2-stearoyl-sn-glycerol-3-phosphorylethanolamine
show the reaction diagram
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-
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?
CDP-ethanolamine + 1-stearoyl-2-oleoylglycerol
CMP + 1-stearoyl-2-oleoylphosphatidylethanolamine
show the reaction diagram
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?
CDP-ethanolamine + 1-stearoylglycerol
CMP + ?
show the reaction diagram
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?
CDP-ethanolamine + 2-oleoylglycerol
CMP + ?
show the reaction diagram
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-
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?
CDP-ethanolamine + diacylglycerol
phosphatidylethanolamine + CMP
show the reaction diagram
CDP-ethanolamine + dipalmitoylglycerol
CMP + dipalmitoylphosphatidylethanolamine
show the reaction diagram
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?
CDP-monomethylethanolamine + 1,2-diacylglycerol
CMP + phosphatidylmonomethylethanolamine
show the reaction diagram
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CDP-monomethylethanolamine is the preferred substrate for enzyme form Ept1p
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?
CDP-propanolamine + 1,2-diacylglycerol
CMP + phosphatidylpropanolamine
show the reaction diagram
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-
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?
lysophosphatidylcholine + CMP
?
show the reaction diagram
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75% of the activity with phosphatidylethanolamine
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r
lysophosphatidylethanolamine + CMP
?
show the reaction diagram
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74% of the activity with phosphatidylethanolamine
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r
phosphatidylcholine + CMP
CDP-choline + diacylglycerol
show the reaction diagram
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
CDP-choline + 1,2-diacyl-sn-glycerol
CMP + a phosphatidylcholine
show the reaction diagram
Q9Y6K0
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-
-
r
CDP-ethanolamine + 1,2-diacyl-sn-glycerol
CMP + a phosphatidylethanolamine
show the reaction diagram
CDP-ethanolamine + 1,2-diacylglycerol
CMP + a phosphatidylethanolamine
show the reaction diagram
CDP-ethanolamine + diacylglycerol
phosphatidylethanolamine + CMP
show the reaction diagram
Q8WU57, Q9C0D9
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?
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
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with substrate 1,2-diacylglycerol, no effect, with substrate 1-O-alk-1’-enyl-2-acyl-sn-glycerol, inhibitory
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,2-Dilaurin
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slight
1-alkyl-2-acyl-sn-glycerol
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inhibits formation of 1,2-diacyl-sn-glycero-3-phosphorylethanolamine
4-chloromercuribenzoate
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5,5'-dithiobis(nitrobenzoic acid)
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substrate 1,2-diacylglycerol
5-hydroxytryptamine
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substrate: diacylglycerol
Acetylcholine
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substrate: diacylglycerol
CDP-choline
CDP-ethanolamine
chelerythrine
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protein kinase C inhibitor, IC50 0.04 mM
cholesterol
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Cytidine nucleotides
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exposure of glomerular particles to
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DH-990
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hypolidemic drug
dipalmitoylphosphatidylcholine
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Dipalmitoylphosphatidylethanolamine
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dithiothreitol
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ethylene glycol-bis(beta-aminoethyl ether)-N,N,N',N'-tetracetic acid
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lysophosphatidylserine
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methanol
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Microsomal phospholipids
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myristic acid
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N-ethylmaleimide
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N-Methyl-D-aspartate
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strong
norepinephrine
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substrate: diacylglycerol or alkylacylglycerol
octyl glucoside
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activates at low concentration, inhibits at higher concentration
p-hydroxymercuribenzoate
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reversal by monothioglycerol
palmitoyl-CoA
phosphatidic acid
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phosphatidylethanolamine
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R59949
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human DAG kinase inhibitor, IC50 0.04 mM
reduced glutathione
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Triton WR 1339
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Tween 20
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,2-diacylglycerol
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stimulated by exogenous 1,2-diacylglycerols, largest stimulation by 1,2-diolein and 1,2-diacylglycerol
5,5'-dithiobis(nitrobenzoic acid)
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i.e. DTNB, substrate 1-O-alk-1’-enyl-2-acyl-sn-glycerol
bovine serum albumin
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1 mg/ml, 2fold increase of activity
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CHAPS
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activates
deoxycholate
diolein
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stimulates, but has no effect on glyceryl ether content of phosphatidylethanolamine
Dipalmitin
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stimulates, but has no effect on glyceryl ether content of phosphatidylethanolamine
EGTA
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stimulates
lysophosphatidylcholine
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increases activity
octyl glucoside
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activates at low concentration, inhibits at higher concentration
phosphatidylcholine
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increases activity
phosphatidylserine
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increases activity
Phospholipid
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absolute requirement
pospholipase C
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10 min, 23°C, 26% stimulation
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taurocholate
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Triton X-100
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slightly stimulates with Mn2+, but not with Mg2+ as cofactor
unsaturated fatty acids
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very slight stimulation
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additional information
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the rate of incorporation of CMP into CDP-ethanolamine is increased by increasing the concentration of phosphatidylethanolamine in detergent-phospholipid micellar system
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0118 - 0.147
1,2-dioleoylglycerol
1.9
1-alkyl-2-acyl-sn-glycerol
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0.182
1-arachidoyl-2-octadecenoylglycerol
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i.e. 1-C20:0,2-C18:1glycerol, 30°C, pH 8.0
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0.111
1-dodecanoyl-2-octadecenoylglycerol
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i.e. 1-C16:0,2-C18:1glycerol, 30°C, pH 8.0
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0.12
1-heptadecanoyl-2-octadecenoylglycerol
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i.e. 1-C17:0,2-C18:1glycerol, 30°C, pH 8.0
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0.128
1-nonadecanoyl-2-octadecenoylglycerol
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i.e. 1-C19:0,2-C18:1glycerol, 30°C, pH 8.0
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0.167
1-octadecanoyl-2-octadecenoylglycerol
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i.e. 1-C18:0,2-C18:1glycerol, 30°C, pH 8.0
0.114
1-pentadecanoyl-2-octadecenoylglycerol
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i.e. 1-C15:0,2-C18:1glycerol, 30°C, pH 8.0
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0.036 - 10.7
CDP-choline
0.00057 - 1800
CDP-ethanolamine
0.04 - 0.14
CMP
0.063
diacylglycerol
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30°C, pH 8.0
additional information
additional information
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.04
chelerythrine
Homo sapiens
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protein kinase C inhibitor, IC50 0.04 mM
0.04
R59949
Homo sapiens
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human DAG kinase inhibitor, IC50 0.04 mM
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0133
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37°C, pH 8.2
0.0763
5 mM Mn2+, pH 8, 37°C
1.705
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37°C, pH 8.2
12.1
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30°C, pH 8.5
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.5 - 9.3
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
temperature dependence
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.1
deduced from primary structure
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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glomeruli
Manually annotated by BRENDA team
RT-PCR and Northern blot
Manually annotated by BRENDA team
low expression levels, revealed by RT-PCR and Northern blot
Manually annotated by BRENDA team
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enzyme activity increases progressively through S and G2/M phases to a level that is 126% of unsynchronized cells
Manually annotated by BRENDA team
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of intestine
Manually annotated by BRENDA team
RT-PCR and Northern blot
Manually annotated by BRENDA team
RT-PCR and Northern blot
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
RT-PCR and Northern blot
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
38000
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x * 38000, SDS-PAGE
44500
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x * 44500, deduced from gene sequence
45180
deduced from primary structure
46500
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x * 46500, SDS-PAGE and deduced from gene sequence
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
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stable for 19 min, heating of microsomes
49
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4 min, more than 50% loss of activity
50
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t1/2: 8 min
55
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1 min, 90% loss of activity
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
enzyme in rat liver microsomes remains unaffected even if over 90% and almost 100% of microsomal phosphatidylcholine and phosphatidylethanolamine is hydrolyzed by snake venom phospholipase A2
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glycerol, diacylglycerol, phosphatidylcholine or lysophosphatidylcholine stabilizes
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lyophilization inhibits
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phospholipase A2 treatment of microsomes decreases activity probably due to disruption of membrane structure
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stable if treated with 0.5% Triton X-100
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Triton X-100, stable to
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trypsin, 70%, 0.9 min, activity remains stable
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-18°C, solubilized enzyme is stable for 3 weeks
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-20°C, stable for more than 2 weeks at any stage of purification
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4°C, solubilized enzyme is stable for 5 days
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below -20°C, stable for more than 1 month, microsomal preparation
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solubilized enzyme is stable for long periods of time
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
membrane precipitation by centrifugation a 100000g for 60 min
overview
partial
shows activities of both EC 2.7.8.1 and EC 2.7.8.2
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solubilization
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
fom cDNA in pET23a for expression in Escherichia coli BL21 (DE3) pLysS
gene bbc, DNA and amino acid sequence determination and analysis, phylogenetic analysis, recombinant expression from vector mammalian expression vector pcDNA3.1/V5-His-TOPO in HeLa cells and in Drosophila S2 cells
overview
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression of the gene encoding CPT, EC 2.7.8.2, but not CEPT increases during lipopolysaccahride-induced endoplasmic reticulum biogenesis in B-lymphocytes
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
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exposure of cortical neurons to neurotoxic concentrations of N-methyl-D-aspartate strongly reduces enzymic activity
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