Information on EC 1.14.19.17 - sphingolipid 4-desaturase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.19.17
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RECOMMENDED NAME
GeneOntology No.
sphingolipid 4-desaturase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a dihydroceramide + 2 ferrocytochrome b5 + O2 + 2 H+ = a (4E)-sphing-4-enine ceramide + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
ceramide de novo biosynthesis
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sphingolipid biosynthesis (plants)
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ceramide biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
dihydroceramide,ferrocytochrome b5:oxygen oxidoreductase (4,5-dehydrogenating)
The enzyme, which has been characterized from plants, fungi, and mammals, generates a trans double bond at position 4 of sphinganine bases in sphingolipids [1]. The preferred substrate is dihydroceramide, but the enzyme is also active with dihydroglucosylceramide [2]. Unlike EC 1.14.19.29, sphingolipid 8-desaturase, this enzyme does not contain an integral cytochrome b5 domain [4] and requires an external cytochrome b5 [3]. The product serves as an important signalling molecules in mammals and is required for spermatide differentiation [5].
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
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DELTA4-desaturation is essential for conversion of the ceramide pool with dihydroxy long-chain sphingoid base and C16/C18 fatty acids into glyosylceramide
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
2,4-dinitrophenyl-sphinganine + reduced acceptor + O2 + H+
2,4-dinitorphenyl-sphingosine + acceptor + H2O
show the reaction diagram
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?
dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
show the reaction diagram
dihydroceramide + reduced acceptor + O2 + H+
(4E)-sphing-4-enine ceramide + acceptor + H2O
show the reaction diagram
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-
?
dihydrosphingomyelin + NADH + O2 + H+
?
show the reaction diagram
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20% activity compared to N-octanoyl-D-erythro-C18-sphinganine
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?
N-hexanoyl-[4,5-3H]sphinganine + NADPH + O2 + H+
?
show the reaction diagram
Q564H3
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-
?
N-octanoyl-D-erythro-C18-sphinganine + NADH + O2 + H+
N-octanoyl-D-erythro-C18-sphingosine + NAD+ + H2O
show the reaction diagram
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-
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?
N-octanoyl-D-erythro-C18-sphinganine + NADPH + O2 + H+
N-octanoyl-D-erythro-C18-sphingosine + NADP+ + H2O
show the reaction diagram
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?
N-octanoyldihydroceramide + NAD(P)H + O2 + H+
?
show the reaction diagram
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?
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
dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
show the reaction diagram
dihydroceramide + reduced acceptor + O2 + H+
(4E)-sphing-4-enine ceramide + acceptor + H2O
show the reaction diagram
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome b5
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NADPH
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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not affected by Ca2+, Mg2+, Mn2+, Fe2+, K+, and Na+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
alpha-cyclodextrin
Q564H3
18% residual activity at a substrate/cyclodextrin molar ratio of 0.5
alpha-linolenic acid
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ascorbic acid
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inhibitory at high concentrations
beta-cyclodextrin
Q564H3
20% residual activity at a substrate/cyclodextrin molar ratio of 0.5
Brij-35
Q564H3
13% residual activity at 0.1 mM
CHAPS
Q564H3
3.0% residual activity at 6.5 mM
Cu2+
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25% inhibition at 1 mM
decylmaltoside
Q564H3
27% residual activity at 1.6 mM
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dithiothreitol
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81% inhibition at 1 mM
lauryl-N,N-dimethylamine
Q564H3
28% residual activity at 2.1 mM
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linoleic acid
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N-acetylcysteine
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N-dodeylsarcosine
Q564H3
complete inhibition at 14.6 mM
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N-octyl-N,N-dimethyl-3-ammonio-1-propane sulfonate
Q564H3
18% residual activity at 330 mM
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octylglucoside
Q564H3
8.5% residual activity at 25 mM
palmitic acid
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SDS
Q564H3
0.3% residual activity at 0.24% (w/v)
sucrose monolaurate
Q564H3
27% residual activity at 0.2 mM
Thesit
Q564H3
23% residual activity at 0.1 mM
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Triton X-100
Q564H3
13% residual activity at 0.25 mM
additional information
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not inhibited by EDTA and Na2SO4
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
albumin
Q564H3
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myristic acid
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.34
N-octanoyl-D-erythro-C18-sphinganine
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at pH 7.4 and 37C
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0.00148
N-octanoyldihydroceramide
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at pH 7.4 and 37C
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0.12
NADH
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with N-octanoyl-D-erythro-C18-sphinganine as cosubstrate, at pH 7.4 and 37C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.031
Cu2+
Rattus norvegicus
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at pH 7.4 and 37C
0.1
cyanide
Rattus norvegicus
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at pH 7.4 and 37C
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
27 - 47
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the half-maximal enzymatic activities are at 27C and 47C. Above 60C, no activity is detected
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
Q564H3
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Manually annotated by BRENDA team
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pollen-specific enzyme
Manually annotated by BRENDA team
additional information
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not detected in root, stem, and leaf
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 40000, V5-His-tagged fusion protein, SDS-PAGE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-4C, phosphate buffer (100 mM NaH2PO4/Na2HPO4, pH 7.4), 7 days, approximately 50% of the activity is lost
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-80C, phosphate buffer (100 mM NaH2PO4/Na2HPO4, pH 7.4), 1 year, approximately 50% of the activity is lost
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37C, phosphate buffer (100 mM NaH2PO4/Na2HPO4, pH 7.4), 3 h, approximately 50% of the activity is lost
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
HisTrap column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in COS-7 cells
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expressed in in Cos-7 cells
expressed in Saccharomyces cerevisiae strain sur2DELTA
expressed in Saccharomyces cerevisiae strain w303-1a