1.14.19.4: acyl-lipid (11-3)-desaturase
This is an abbreviated version!
For detailed information about acyl-lipid (11-3)-desaturase, go to the full flat file.
Word Map on EC 1.14.19.4
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1.14.19.4
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desaturases
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polyunsaturated
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desaturation
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sphingolipids
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delta6
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arachidonic
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front-end
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gracilis
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sphingoid
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euglena
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eicosatrienoic
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borago
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ozonolysis
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galbana
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delta6-fatty
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tetraene
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isochrysis
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dinitrophenyl
- 1.14.19.4
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desaturases
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polyunsaturated
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desaturation
- sphingolipids
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delta6
-
arachidonic
-
front-end
- gracilis
-
sphingoid
- euglena
-
eicosatrienoic
-
borago
-
ozonolysis
- galbana
-
delta6-fatty
-
tetraene
- isochrysis
-
dinitrophenyl
Reaction
+ 2 ferrocytochrome b5 + + 2 H+ = + 2 ferricytochrome b5 + 2 H2O
Synonyms
AtSLD1, AtSLD2, Boofd8, Ca-SLDp, D8A, DELTA6-desaturase, DELTA8 acyl-CoA-dependent desaturase, DELTA8 desaturase, DELTA8 sphingobase desaturase, Delta8 sphingolipid desaturase, DELTA8-desaturase, DELTA8-fatty-acid desaturase, DELTA8-sphingolipid desaturase, FADS2, SLD, SlSLD, sphingolipid delta8 desaturase, sphingolipid DELTA8 LCB desaturase, sphingolipid DELTA8 long-chain base desaturase, sphingolipid DELTA8-desaturase, TpdesB
ECTree
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Substrates Products
Substrates Products on EC 1.14.19.4 - acyl-lipid (11-3)-desaturase
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REACTION DIAGRAM
(2S,3R)-2-aminoicosane-1,3-diol + reduced acceptor + O2
(E)-(2S,3R)-2-aminoicos-8-ene-1,3-diol + (Z)-(2S,3R)-2-aminoicos-8-ene-1,3-diol + acceptor + H2O
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-
-
-
?
(E)-sphing-4-enine + reduced acceptor + O2
(2S,3R,4E,8E)-2-aminooctadeca-4,8-diene-1,3-diol + acceptor + H2O
(R)-9-fluorophytosphinganine + reduced acceptor + O2
(Z)-9-fluoro-8-phytosphingenine + acceptor + H2O
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exclusively produces (Z)-9-fluoro-8-phytosphingenine. This result is explained by an initial attack onto the C8-HR and syn-elimination of two vicinal hydrogen atoms via an anti-conformation of the substrate. An initial attack on the C9-F is excluded and generates no product
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-
?
(S)-8-fluorophytosphinganine + reduced acceptor + O2
(Z)-8-fluoro-8-phytosphingenine + acceptor + H2O
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product predominantly transformed to (Z)-8-fluoro-8-phytosphingenine along with only trace amounts of the (E)-8-fluoro-8-phytosphingenine (ratio 95:5). This ratio indicates that the fluorinated substrate strongly favors the anti-configuration at the active center of the desaturase
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-
?
(S)-9-fluorophytosphinganine + reduced acceptor + O2
(E)-9-fluoro-8-phytosphingenine + acceptor + H2O
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produces (E)-9-fluoro-8-phytosphingenine as the sole reaction product. Only the initial attack on the C9-HR in combination with the gauche-conformation of the substrate is productive
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-
?
11,14,17-eicosatrienoic acid + reduced acceptor + O2
8,11,14,17-eicosatetraenoic acid + acceptor + H2O
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-
-
?
11,14,17-eicosatrienoic acid + reduced acceptor + O2
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20:3n-3, yield 20:4n-3
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-
?
11,14-eicosadienoic acid + reduced acceptor + O2
8,11,14-eicosatrienoic acid + acceptor + H2O
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-
-
?
11,14-eicosadienoic acid + reduced acceptor + O2
?
20:2n-6, yield 20:3n-6
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-
?
11-eicosenoic acid + reduced acceptor + O2
8,11-eicosadienoic acid + acceptor + H2O
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-
-
?
4-hydroxysphinganine + reduced acceptor + H2O
4-hydroxy-trans-8-sphingenine + acceptor + H2O
DELTA4-sphingenine + reduced acceptor + O2
DELTA4,8-sphingadienine + acceptor + 2 H2O
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production of two water molecules in the reaction
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?
phytosphinganine + reduced acceptor + O2
(8E)-4-hydroxy-8-sphingenine + (8Z)-4-hydroxy-8-sphingenine + acceptor + H2O
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reaction in a in a stereospecific manner by syn elimination of two vicinal hydrogen atoms
production of two water molecules in the reaction
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?
phytosphinganine + reduced acceptor + O2
DELTA8-phytosphingenine + acceptor + H2O
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production of two water molecules in the reaction
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?
phytosphinganine + reduced acceptor + O2
trans-8-sphingenine + cis-8-sphingenine + acceptor + H2O
sphinganine + reduced acceptor + O2
DELTA8-sphingenine + acceptor + 2 H2O
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production of two water molecules in the reaction
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?
(2S,3R,4E,8E)-2-aminooctadeca-4,8-diene-1,3-diol + acceptor + H2O
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-
-
-
?
(E)-sphing-4-enine + reduced acceptor + O2
(2S,3R,4E,8E)-2-aminooctadeca-4,8-diene-1,3-diol + acceptor + H2O
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-
-
-
?
4-hydroxy-trans-8-sphingenine + acceptor + H2O
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-
-
?
4-hydroxysphinganine + reduced acceptor + H2O
4-hydroxy-trans-8-sphingenine + acceptor + H2O
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-
-
-
?
trans-8-sphingenine + cis-8-sphingenine + acceptor + H2O
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-
-
?
phytosphinganine + reduced acceptor + O2
trans-8-sphingenine + cis-8-sphingenine + acceptor + H2O
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-
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?
?
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desaturation of long-chain base moieties of sphingolipid classes (ceramide, hydroxyceramide, GlcCer, and GIPC) during cold treatment, overview
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-
?
additional information
?
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desaturation of long-chain base moieties of sphingolipid classes (ceramide, hydroxyceramide, GlcCer, and GIPC) during cold treatment, overview
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-
?
additional information
?
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desaturation of long-chain base moieties of sphingolipid classes (ceramide, hydroxyceramide, GlcCer, and GIPC) during cold treatment, overview
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-
?
additional information
?
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desaturation of long-chain base moieties of sphingolipid classes (ceramide, hydroxyceramide, GlcCer, and GIPC) during cold treatment, overview
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-
?
additional information
?
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(R)-8-fluorophytosphinganine does not yield any desaturation product
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-
?
additional information
?
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DELTA8 sphingolipid desaturase creates double bonds in long-chain bases, i.e. sphingobases, such as sphinganine, phytosphinganine, or 4-sphingenine to produce E- and Z-isomers of 8-sphingenine, 8-phytosphingenine, or 4,8-sphingadienine, respectively
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-
?
additional information
?
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DELTA8 sphingolipid desaturase creates double bonds in long-chain bases, i.e. sphingobases, such as sphinganine, phytosphinganine, or 4-sphingenine to produce E- and Z-isomers of 8-sphingenine, 8-phytosphingenine, or 4,8-sphingadienine, respectively
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-
?