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Information on EC 1.14.19.77 - plasmanylethanolamine desaturase
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1.14.19.77 plasmanylethanolamine desaturaseIUBMB Comments
The enzyme catalyses the introduction of a double bond at position 1 of the alkyl group attached by an ether bond at the sn-1 position of plasmanylethanolamine, generating a vinyl ether-containing plasmenylethanolamine. The enzyme is found in animals and some bacteria, but not in plants, fungi, or most aerobic bacteria.
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Word Map
- 1.14.19.77
- plasmalogens
- ether
- phospholipids
-
vinyl
-
plasmalogen-deficient
-
macrophage-like
-
zoeller
-
arachidonic
-
orphan
- glycerophospholipids
-
desaturases
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
a plasmanylethanolamine
+
2
+
+
2
=
a plasmenylethanolamine
+
2
+
2
Synonyms
plasmanylethanolamine desaturase, tmem189, delta1'-desaturase, alkylacylglycerophosphoethanolamine desaturase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
1-O-alkyl-2-acyl-sn-glycero-3-phosphorylethanolamine desaturase
-
-
-
-
alkylacylglycero-phosphorylethanolamine dehydrogenase
-
-
-
-
alkylacylglycerophosphoethanolamine desaturase
-
-
-
-
dehydrogenase, alkyl-acylglycerophosphorylethanolamine
-
-
-
-
desaturase, alkylacylglycerophosphorylethanolamine
-
-
-
-
plasmanylethanolamine D1-desaturase
TMEM189
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a plasmanylethanolamine + 2 ferrocytochrome b5 + O2 + 2 H+ = a plasmenylethanolamine + 2 ferricytochrome b5 + 2 H2O
a plasmanylethanolamine + 2 ferrocytochrome b5 + O2 + 2 H+ = a plasmenylethanolamine + 2 ferricytochrome b5 + 2 H2O
mixed function oxidase
-
a plasmanylethanolamine + 2 ferrocytochrome b5 + O2 + 2 H+ = a plasmenylethanolamine + 2 ferricytochrome b5 + 2 H2O
mixed function oxidase
-
a plasmanylethanolamine + 2 ferrocytochrome b5 + O2 + 2 H+ = a plasmenylethanolamine + 2 ferricytochrome b5 + 2 H2O
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
plasmanylethanolamine,ferrocytochrome b5:oxygen oxidoreductase (plasmenylethanolamine-forming)
The enzyme catalyses the introduction of a double bond at position 1 of the alkyl group attached by an ether bond at the sn-1 position of plasmanylethanolamine, generating a vinyl ether-containing plasmenylethanolamine. The enzyme is found in animals and some bacteria, but not in plants, fungi, or most aerobic bacteria.
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CAS REGISTRY NUMBER
COMMENTARY
39391-13-4
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1-hexadecyl-2-acyl glycero-3-phosphoethanolamine + NADH + O2
?
-
in situ in the microsomes via acylation of 1-hexadecyl-glycero-3-phosphoethanolamine
-
-
?
1-O-hexadecyl-rac-glycero-3-phosphorylethanolamine + NADPH + O2 + H+
?
-
good substrate
-
-
?
a plasmanylethanolamine + 2 ferrocytochrome b5 + O2 + 2 H+
a plasmenylethanolamine + 2 ferricytochrome b5 + 2 H2O
alkyl ether plasmanylethanolamine + NADPH + O2
vinyl ether phosphatidylethanolamine + NADP+ + H2O
iso15:0-O-alkylglycerol-bis-trimethylsilyl ether + NADPH + O2
iso15:0-dimethylacetal + NADP+ + H2O
-
-
-
?
iso16:0-O-alkylglycerol-bis-trimethylsilyl ether + NADPH + O2
iso16:0-dimethylacetal + NADP+ + H2O
-
-
-
?
iso18:0-O-alkylglycerol-bis-trimethylsilyl ether + NADPH + O2
iso18:0-dimethylacetal + NADP+ + H2O
-
-
-
?
iso18:1-O-alkylglycerol-bis-trimethylsilyl ether + NADPH + O2
iso18:1-dimethylacetal + NADP+ + H2O
-
-
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + AH2 + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + A + 2 H2O
-
i.e. plasmanylethanolamine
i.e. plasmenylethanolamine
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + electron donor + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized electron donor + H2O
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + reduced cytochrome b5 + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized cytochrome b5 + 2 H2O
-
i.e. plasmanylethanolamine, the reaction involves reaction involving cytochrome b5 reductase, molecular oxygen and a reduction equivalent
i.e. plasmenylethanolamine
-
?
[1-3H ethanolamine]-1-alkyl-2-lyso-sn-glycero-3-phosphoethanolamine + NADH + O2 + H+
?
-
-
-
-
?
a plasmanylethanolamine + 2 ferrocytochrome b5 + O2 + 2 H+
a plasmenylethanolamine + 2 ferricytochrome b5 + 2 H2O
-
-
-
-
?
a plasmanylethanolamine + 2 ferrocytochrome b5 + O2 + 2 H+
a plasmenylethanolamine + 2 ferricytochrome b5 + 2 H2O
-
-
-
-
?
alkyl ether plasmanylethanolamine + NADPH + O2
vinyl ether phosphatidylethanolamine + NADP+ + H2O
-
-
-
?
alkyl ether plasmanylethanolamine + NADPH + O2
vinyl ether phosphatidylethanolamine + NADP+ + H2O
-
-
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + electron donor + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized electron donor + H2O
-
-
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + electron donor + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized electron donor + H2O
-
generated in situ by microsomal acylation of alkyllyso-glycero-3-phosphoethanolamine, better substrate than when it is added exogenously
-
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + electron donor + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized electron donor + H2O
-
-
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + electron donor + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized electron donor + H2O
-
generated in situ by microsomal acylation of alkyllyso-glycero-3-phosphoethanolamine, better substrate than when it is added exogenously
-
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + electron donor + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized electron donor + H2O
-
generated in situ by microsomal acylation of alkyllyso-glycero-3-phosphoethanolamine, better substrate than when it is added exogenously
-
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + electron donor + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized electron donor + H2O
-
-
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + electron donor + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized electron donor + H2O
-
-
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + electron donor + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized electron donor + H2O
-
-
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + electron donor + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized electron donor + H2O
-
generated in situ by microsomal acylation of alkyllyso-glycero-3-phosphoethanolamine, better substrate than when it is added exogenously
-
-
?
additional information
?
-
-
the enzyme converts plasmanylethanolamine into plasmenylethanolamine by introducing a vinyl double bound. It requires cytochrome b5, molecular oxygen and either NADPH or NADH as cofactors for functional catalysis. Plasmanylcholines are no substrates for plasmanylethanolamine desaturase
-
-
?
additional information
?
-
-
no substrates: O-3-alkyl-2-acyl-sn-glycero-1-phosphoethanolamine, octadecylglycerol, octadecanal, octadecanol, stearic acid
-
-
?
additional information
?
-
-
highly specific with regard to chain length of saturated alkyl moieties of alkylacylglycerophosphoethanolamines
-
-
?
additional information
?
-
-
high degree of substrate specificity, no substrate is O-1-alkyl-ethanediol-2-phosphoethanolamine
-
-
?
additional information
?
-
-
no selectivity of the desaturase for specific acyl chains
-
-
?
additional information
?
-
-
highly specific with regard to chain length of saturated alkyl moieties of alkylacylglycerophosphoethanolamines
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
a plasmanylethanolamine + 2 ferrocytochrome b5 + O2 + 2 H+
a plasmenylethanolamine + 2 ferricytochrome b5 + 2 H2O
alkyl ether plasmanylethanolamine + NADPH + O2
vinyl ether phosphatidylethanolamine + NADP+ + H2O
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + AH2 + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + A + 2 H2O
-
i.e. plasmanylethanolamine
i.e. plasmenylethanolamine
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + electron donor + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized electron donor + H2O
a plasmanylethanolamine + 2 ferrocytochrome b5 + O2 + 2 H+
a plasmenylethanolamine + 2 ferricytochrome b5 + 2 H2O
-
-
-
-
?
a plasmanylethanolamine + 2 ferrocytochrome b5 + O2 + 2 H+
a plasmenylethanolamine + 2 ferricytochrome b5 + 2 H2O
-
-
-
-
?
alkyl ether plasmanylethanolamine + NADPH + O2
vinyl ether phosphatidylethanolamine + NADP+ + H2O
-
-
-
?
alkyl ether plasmanylethanolamine + NADPH + O2
vinyl ether phosphatidylethanolamine + NADP+ + H2O
-
-
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + electron donor + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized electron donor + H2O
-
-
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + electron donor + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized electron donor + H2O
-
-
-
?
O-1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + electron donor + O2
O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + oxidized electron donor + H2O
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
heat-lable factor of high molecular weight
-
contained in the 100000 * g supernatant
-
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
plasmanylethanolamine desaturase deficiency
Unequivocal Mapping of Molecular Ether Lipid Species by LC-MS/MS in Plasmalogen-Deficient Mice.
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.0000028
-
microsomes plus soluble fraction, enzyme requires a heat-labile factor of high molecular weight contained in the soluble fraction
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
microsomal membrane, advisable to check the effect of the soluble fraction
-
brenda
-
microsomal membrane, advisable to check the effect of the soluble fraction
-
brenda
-
microsomal membrane, advisable to check the effect of the soluble fraction
-
brenda
-
microsomal membrane, advisable to check the effect of the soluble fraction
-
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
-
plasmanylethanolamine desaturase is a key enzyme for the biosynthesis of one of the most abundant phospholipidsin the body, the plasmalogens. Ether lipid metabolism including biosynthesis and degradation of platelet-activating factor and plasmalogens, overview
physiological function
the enzyme mediates light-induced carotenogenesis and and plasmalogen formation in Myxococcus xanthus
additional information
-
the enzyme is a defined enzyme without assigned sequence, these kind of enzymes are known as orphan enzymes
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). PDES1_BOVIN
271
0
31285
Swiss-Prot
other Location (Reliability: 2)
PDES1_HUMAN
270
3
31135
Swiss-Prot
other Location (Reliability: 2)
PDES1_MOUSE
271
2
31134
Swiss-Prot
other Location (Reliability: 2)
A0A803JR74_XENTR
289
3
33283
TrEMBL
other Location (Reliability: 2)
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
H121A
H131A
-
the mutant show strongly reduced activity compared to the wild type enzyme
H218A
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Paltauf, F.; Holasek, A.
Enzymatic synthesis of plasmalogens. Characterization of the 1-O-alkyl-2-acyl-8n-glycero-3-phosphorylethanolamine desaturase from mucosa of hamster small intestine
J. Biol. Chem.
248
1609-1615
1973
Mesocricetus auratus
brenda
Wykle, R.L.; Blank, M.L.; Malone, B.; Snyder, F.
Evidence for a mixed function oxidase in the biosynthesis of ethanolamine plasmalogens from 1-alkyl-2-acyl-sn-glycero-3-phosphorylethanolamine
J. Biol. Chem.
247
5442-5447
1972
Rattus norvegicus
brenda
Lee, F.C.; Wykle, R.L.; Blank, M.L.; Snyder, F.
Dietary control of stearyl CoA and alkylacylglycerophosphorylethanolamine desaturases in tumor
Biochem. Biophys. Res. Commun.
55
574-579
1973
Rattus norvegicus
brenda
Wykle, R.L.; Schremmer, J.M.
Biosynthesis of plasmalogens by the microsomal fraction of Fischer R-3259 sarcoma. Influence of specific 2-acyl chains on the desaturation of 1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine
Biochemistry
18
3512-3517
1979
Rattus norvegicus
brenda
Weber, N.; Richter, J.
Formation of ether lipids and wax esters in mammalian cells. Specificity of enzymes with regard to carbon chains of substrates
Biochim. Biophys. Acta
711
197-207
1982
Mus musculus, Rattus norvegicus
brenda
Baumann, W.J.; Madson, T.H.; Chang, N.; Bandi, P.C.; Schmidt, H.H.O.
On the substrate specificity of enol ether formation in rat brain. Metabolism of O-alkyl ethanediol phosphorylethanolamine
Biochem. Biophys. Res. Commun.
66
717-724
1975
Rattus norvegicus
brenda
Das, A.K.; Hajra, A.K.
A novel chemical synthesis of 1-O-hexadecyl-rac-[2-3H]glycero-3-phosphorylethanolamine and a simple assay for plasmanyl desaturase
J. Lipid Res.
37
2706-2714
1996
Rattus norvegicus
brenda
Blank, M.L.; Snyder, F.
Plasmanylethanolamine D1-desaturase
Methods Enzymol.
209
390-396
1992
Mesocricetus auratus, Mus musculus, Oryctolagus cuniculus, Rattus norvegicus
brenda
Watschinger, K.; Werner, E.R.
Orphan enzymes in ether lipid metabolism
Biochimie
95
59-65
2013
Homo sapiens
brenda
Gallego-Garcia, A.; Monera-Girona, A.J.; Pajares-Martinez, E.; Bastida-Martinez, E.; Perez-Castano, R.; Iniesta, A.A.; Fontes, M.; Padmanabhan, S.; Elias-Arnanz, M.
A bacterial light response reveals an orphan desaturase for human plasmalogen synthesis
Science
366
128-132
2019
Homo sapiens (A5PLL7), Homo sapiens, Myxococcus xanthus (Q9AE87), Myxococcus xanthus
brenda
Rangaswamy, S.; Zoeller, R.A.
Fatty acid desaturation in an animal cell mutant defective in plasmanylethanolamine desaturase
Biochim. Biophys. Acta
1211
79-84
1994
Mus musculus
brenda
Das, A.; Hajra, A.
A novel chemical synthesis of 1-O-hexadecyl-rac-[2-3H]glycero-3-phosphorylethanolamine and a simple assay for plasmanyl desaturase
J. Lipid Res.
37
2706-2714
1996
Rattus norvegicus
brenda
Werner, E.R.; Keller, M.A.; Sailer, S.; Lackner, K.; Koch, J.; Hermann, M.; Coassin, S.; Golderer, G.; Werner-Felmayer, G.; Zoeller, R.A.; Hulo, N.; Berger, J.; Watschinger, K.
The TMEM189 gene encodes plasmanylethanolamine desaturase which introduces the characteristic vinyl ether double bond into plasmalogens
Proc. Natl. Acad. Sci. USA
117
7792-7798
2020
Homo sapiens
brenda
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