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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
-
-
?
1-O-pyrenedecyl-sn-glycero-3-phosphoethanolamine + NADPH + O2 + H+
?
-
-
-
-
?
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
-
?
O-1-hexadecyl-rac-glycero-3-phosphoethanolamine + NADPH + O2
?
-
-
-
-
?
[1-3H ethanolamine]-1-alkyl-2-lyso-sn-glycero-3-phosphoethanolamine + NADH + O2 + H+
?
-
-
-
-
?
additional information
?
-
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
?
-
-
electron donors: NADPH or NADH
-
-
?
additional information
?
-
-
electron donors: NADPH or NADH
-
-
?
additional information
?
-
-
electron donors: NADPH or NADH
-
-
?
additional information
?
-
-
highly specific with regard to chain length of saturated alkyl moieties of alkylacylglycerophosphoethanolamines
-
-
?
additional information
?
-
-
electron donors: NADPH or NADH
-
-
?
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
?
-
-
electron donors: NADPH or NADH
-
-
?
additional information
?
-
-
highly specific with regard to chain length of saturated alkyl moieties of alkylacylglycerophosphoethanolamines
-
-
?
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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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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