Information on EC 1.14.19.29 - sphingolipid 8-(E/Z)-desaturase

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)

The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.19.29
-
RECOMMENDED NAME
GeneOntology No.
sphingolipid 8-(E/Z)-desaturase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a (4R)-4-hydroxysphinganine ceramide + 2 ferrocytochrome b5 + O2 + 2 H+ = a (4R,8E)-4-hydroxysphing-8-enine ceramide + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
a (4R)-4-hydroxysphinganine ceramide + 2 ferrocytochrome b5 + O2 + 2 H+ = a (4R,8Z)-4-hydroxysphing-8-enine ceramide + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
sphingolipid biosynthesis (plants)
-
-
SYSTEMATIC NAME
IUBMB Comments
(4R)-4-hydroxysphinganine ceramide,ferrocytochrome b5:oxygen oxidoreductase (8,9 cis/trans-dehydrogenating)
The enzymes from higher plants convert sphinganine, 4E-sphing-4-enine and phytosphinganine into E/Z-mixtures of Delta8-desaturated products displaying different proportions of geometrical isomers depending on plant species. The nature of the actual desaturase substrate has not yet been studied experimentally. The enzymes contain an N-terminal cytochrome b5 domain that acts as the direct electron donor to the active site of the desaturase [1]. The homologous enzymes from some yeasts and diatoms, EC 1.14.19.18, sphingolipid 8-(E)-desaturase, act on sphing-4-enine ceramides and produce only the trans isomer.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
variety Wisconsin-38
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + (4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
show the reaction diagram
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
show the reaction diagram
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
show the reaction diagram
(E)-sphing-4-enine + ferrocytochrome b5 + O2 + H+
(4E,8E)-sphinga-4,8-dienine + ferricytochrome b5 + H2O
show the reaction diagram
C18-phytosphinganine + ferrocytochrome b5 + O2 + H+
C18-8-phytosphingenine + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
?
C18-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C18-phytosphingenine + ferricytochrome b5 + H2O
show the reaction diagram
C20-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C-20-phytosphingenine + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
?
C20-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C20-phytosphingenine + ferricytochrome b5 + H2O
show the reaction diagram
fluorinated phytosphinganine + ferrocytochrome b5 + O2 + H+
?
show the reaction diagram
-
the presence of a fluorine atom at the position of the initial hydrogen removal C8-HR leads to a complete suppression of the desaturation reaction, while replacement of C8-HS with fluorine generates a mixture of mainly (Z)- and trace amounts of (E)-fluoroolefine
-
-
?
phytosphinganine + 2 ferrocytochrome b5 + O2 + 2 H+
(4R,8E)-4-hydroxy-8-sphingenine + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
phytosphinganine + 2 ferrocytochrome b5 + O2 + 2 H+
(4R,8Z)-4-hydroxy-8-sphingenine + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
sphinganine + ferrocytochrome b5 + O2 + H+
8-sphingenine + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
?
sphinganine ceramide + ferrocytochrome b5 + O2 + H+
8-sphingenine ceramide + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
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
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + (4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
show the reaction diagram
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
show the reaction diagram
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
show the reaction diagram
(E)-sphing-4-enine + ferrocytochrome b5 + O2 + H+
(4E,8E)-sphinga-4,8-dienine + ferricytochrome b5 + H2O
show the reaction diagram
C18-phytosphinganine + ferrocytochrome b5 + O2 + H+
C18-8-phytosphingenine + ferricytochrome b5 + H2O
show the reaction diagram
Q9FR82
-
-
-
?
C18-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C18-phytosphingenine + ferricytochrome b5 + H2O
show the reaction diagram
C20-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C-20-phytosphingenine + ferricytochrome b5 + H2O
show the reaction diagram
Q43469
-
-
-
?
C20-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C20-phytosphingenine + ferricytochrome b5 + H2O
show the reaction diagram
phytosphinganine + 2 ferrocytochrome b5 + O2 + 2 H+
(4R,8E)-4-hydroxy-8-sphingenine + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
-
-
-
-
?
phytosphinganine + 2 ferrocytochrome b5 + O2 + 2 H+
(4R,8Z)-4-hydroxy-8-sphingenine + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
-
-
(2)
-
?
sphinganine + ferrocytochrome b5 + O2 + H+
8-sphingenine + ferricytochrome b5 + H2O
show the reaction diagram
Q9FR82
-
-
-
?
sphinganine ceramide + ferrocytochrome b5 + O2 + H+
8-sphingenine ceramide + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome b5
-
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
isoform SLD1 and SLD2
Manually annotated by BRENDA team
-
isoform SLD1
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed as chimera protein with DELTA6 fatty acid desaturase in Saccharomyces cervisiae
-
expressed in Saccharomyces cerevisiae
expressed in Saccharomyces cerevisiae and Arabidopsis thaliana
expressed in Saccharomyces cerevisiae BY4741 cells
-
expressed in Saccharomyces cerevisiae strain InvSc1
-
expressed in Saccharomyces cerevisiae strain INVScI
expressed in Saccharomyces cerevisiae strain INVScl mutant sur2DELTA lacking sphinganine C4-hydroxylase
expressed in Saccharomyces cerevisiae strain w303-1a; expression of this openreading frame in Saccharomyces cerevisiae results in the formation of DELTA8-trans/cis-phytosphingenines not present in wild-type cells
-
expressed in Saccharomyces cerevisiae strain W303-A1
expressed in Saccharomyces cerevisiae; the open reading frame is cloned behind the constitutive ADH1 promotor of the yeast expression vector pVT-U-102 and transformed in Saccharomyces cerevisiae INVSc1
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D208R
inactive
D210R
inactive
F59R
the mutant shows severely reduced activity compared to the wild type enzyme
G28R
the mutant shows reduced activity compared to the wild type enzyme
G368R
inactive
G52R
the mutant shows wild type activity
H63R
inactive
L369A
the mutant shows severely reduced activity compared to the wild type enzyme
L71R
the mutant shows wild type activity
N203R
inactive
Q372H
the mutant shows severely reduced activity compared to the wild type enzyme
T56R
the mutant shows reduced activity compared to the wild type enzyme
W190A
the mutant shows severely reduced activity compared to the wild type enzyme
W345A
the mutant shows severely reduced activity compared to the wild type enzyme
Y31A
the mutant shows reduced activity compared to the wild type enzyme