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Information on EC 1.14.19.17 - sphingolipid 4-desaturase Word Map on EC 1.14.19.17
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The enzyme appears in viruses and cellular organisms
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sphingolipid 4-desaturase
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a dihydroceramide + 2 ferrocytochrome b5 + O2 + 2 H+ = a (4E)-sphing-4-enine ceramide + 2 ferricytochrome b5 + 2 H2O
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ceramide de novo biosynthesis
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sphingolipid biosynthesis (plants)
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ceramide biosynthesis
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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].
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degenerative spermatocyte desaturase
dehydroceramide desaturase
dihydroceramide DELTA4-(E)-desaturase
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dihydroceramide DELTA4-desaturase
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dihydroceramide DELTA4-desaturase 1
dihydroceramide desaturase
LCB DELTA4 desaturase
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membrane lipid desaturase
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sphingolipid DELTA4-desaturase
degenerative spermatocyte desaturase
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degenerative spermatocyte desaturase
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dehydroceramide desaturase
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dehydroceramide desaturase
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DES1
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dihydroceramide DELTA4-desaturase 1
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dihydroceramide DELTA4-desaturase 1
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dihydroceramide desaturase
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dihydroceramide desaturase
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dihydroceramide desaturase
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dihydroceramide desaturase
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dihydroceramide desaturase
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dihydroceramide desaturase
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dihydroceramide desaturase
Q564H3
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sphingolipid DELTA4-desaturase
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sphingolipid DELTA4-desaturase
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sphingolipid DELTA4-desaturase
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sphingolipid DELTA4-desaturase
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sphingolipid DELTA4-desaturase
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sphingolipid DELTA4-desaturase
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UniProt
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UniProt
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UniProt
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UniProt
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SwissProt
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UniProt
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UniProt
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SwissProt
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Q564H3
SwissProt
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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
the enzyme has no effect on cell viability
physiological function
DELTA4-desaturated sphingolipids provide an early signal necessary to trigger the entry into both meiotic and spermatid differentiation pathways during spermatogenesis
physiological function
DELTA4-desaturated sphingolipids provide an early signal necessary to trigger the entry into both meiotic and spermatid differentiation pathways during spermatogenesis
physiological function
DELTA4-desaturated sphingolipids provide an early signal necessary to trigger the entry into both meiotic and spermatid differentiation pathways during spermatogenesis
physiological function
DELTA4-desaturated sphingolipids provide an early signal necessary to trigger the entry into both meiotic and spermatid differentiation pathways during spermatogenesis
physiological function
DELTA4-desaturated sphingolipids provide an early signal necessary to trigger the entry into both meiotic and spermatid differentiation pathways during spermatogenesis
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2,4-dinitrophenyl-sphinganine + reduced acceptor + O2 + H+
2,4-dinitorphenyl-sphingosine + acceptor + H2O
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
dihydroceramide + reduced acceptor + O2 + H+
(4E)-sphing-4-enine ceramide + acceptor + H2O
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dihydrosphingomyelin + NADH + O2 + H+
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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+
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Q564H3
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N-octanoyl-D-erythro-C18-sphinganine + NADH + O2 + H+
N-octanoyl-D-erythro-C18-sphingosine + NAD+ + H2O
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?
N-octanoyl-D-erythro-C18-sphinganine + NADPH + O2 + H+
N-octanoyl-D-erythro-C18-sphingosine + NADP+ + H2O
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?
N-octanoyldihydroceramide + NAD(P)H + O2 + H+
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additional information
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
Q564H3
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
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additional information
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no activity detected with dihydroglucosylceramide
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additional information
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the enzyme does not recognise fatty acids and trihydroxylated sphingoid long-chain bases as substrate
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additional information
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the enzyme does not recognise fatty acids and trihydroxylated sphingoid long-chain bases as substrate
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
dihydroceramide + reduced acceptor + O2 + H+
(4E)-sphing-4-enine ceramide + acceptor + H2O
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
G5EC63
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
Q5AJX2
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
Q94515
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
O15121
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
O09005
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
Q564G3
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
Q564H3
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
Q5XIF5
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dihydroceramide + ferrocytochrome b5 + O2 + H+
(4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O
O59715
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cytochrome b5
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NADH
Q564H3
dependent on, higher activity with NADPH compared to NADH
NADPH
Q564H3
dependent on, higher activity with NADPH compared to NADH
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additional information
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not affected by Ca2+, Mg2+, Mn2+, Fe2+, K+, and Na+
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alpha-cyclodextrin
Q564H3
18% residual activity at a substrate/cyclodextrin molar ratio of 0.5
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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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
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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myristic acid
the activity of wild-type isoform DES1 is linearly increased in the presence of increased concentrations of myristic acid. The dihydroceramide DELTA4-desaturase activity of the myristoylable enzyme is reproducibly and significantly higher than the unmyristoylated enzyme
myristic acid
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myristic acid significantly increases DES1 activity in the mitochondria of cultured rat hepatocytes
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0.34
N-octanoyl-D-erythro-C18-sphinganine
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at pH 7.4 and 37°C
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0.00148
N-octanoyldihydroceramide
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at pH 7.4 and 37°C
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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 37°C
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0.031
Cu2+
Rattus norvegicus
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at pH 7.4 and 37°C
0.1
cyanide
Rattus norvegicus
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at pH 7.4 and 37°C
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27 - 47
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the half-maximal enzymatic activities are at 27°C and 47°C. Above 60°C, no activity is detected
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brenda
Q564H3
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Q564H3
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pollen-specific enzyme
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additional information
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not detected in root, stem, and leaf
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N-myristoylation targets dihydroceramide DELTA4-desaturase 1 to mitochondria
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40000
x * 40000, V5-His-tagged fusion protein, SDS-PAGE
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x * 40000, V5-His-tagged fusion protein, SDS-PAGE
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-4°C, phosphate buffer (100 mM NaH2PO4/Na2HPO4, pH 7.4), 7 days, approximately 50% of the activity is lost
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-80°C, phosphate buffer (100 mM NaH2PO4/Na2HPO4, pH 7.4), 1 year, approximately 50% of the activity is lost
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37°C, phosphate buffer (100 mM NaH2PO4/Na2HPO4, pH 7.4), 3 h, approximately 50% of the activity is lost
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HisTrap column chromatography
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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
expressed in Saccharomyces cerevisiae strain sur2DELTA
expressed in Saccharomyces cerevisiae strain sur2DELTA
expressed in Saccharomyces cerevisiae strain sur2DELTA
expressed in Saccharomyces cerevisiae strain sur2DELTA
expressed in Saccharomyces cerevisiae strain sur2DELTA
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DEGS2_CAEEL
362
42316
Swiss-Prot
DEGS1_CAEEL
360
41686
Swiss-Prot
DES1L_ORYSJ
328
37869
Swiss-Prot
DEGS2_BOVIN
323
37319
Swiss-Prot
DEGS1_RAT
323
38055
Swiss-Prot
DEGS1_MOUSE
323
38241
Swiss-Prot
DEGS1_CHICK
323
37975
Swiss-Prot
DEGS1_BOVIN
323
38070
Swiss-Prot
DEGS1_HUMAN
323
37866
Swiss-Prot
DEGS_CANAL
Candida albicans (strain SC5314 / ATCC MYA-2876)
370
43395
Swiss-Prot
DEGS2_RAT
323
37441
Swiss-Prot
DEGS2_MOUSE
323
37491
Swiss-Prot
DEGS2_HUMAN
323
37197
Swiss-Prot
DEGS1_MICFO
323
38066
Swiss-Prot
DEGS_SCHPO
Schizosaccharomyces pombe (strain 972 / ATCC 24843)
362
41810
Swiss-Prot
DEGS1_XENTR
323
37642
Swiss-Prot
DEGS1_PONAB
323
37810
Swiss-Prot
DEGS_KOMPG
Komagataella phaffii (strain GS115 / ATCC 20864)
360
41541
Swiss-Prot
DES1L_ARATH
332
38507
Swiss-Prot
A0A161MCC0_TRIIF
332
38611
TrEMBL
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Asthma
Current status of allergy prevalence in Germany: Position paper of the Environmental Medicine Commission of the Robert Koch Institute.
Carcinoma
Dihydroceramide delays cell cycle G1/S transition via activation of ER stress and induction of autophagy.
Carcinoma
Overexpression of degenerative spermatocyte homolog 1 up-regulates the expression of cyclin D1 and enhances metastatic efficiency in esophageal carcinoma Eca109 cells.
Carcinoma, Squamous Cell
Dihydroceramide desaturase knockdown impacts sphingolipids and apoptosis after photodamage in human head and neck squamous carcinoma cells.
Cholangiocarcinoma
Dihydroceramide desaturase activity in tumors.
Coronary Disease
[Prevalence of myocardial infarction and coronary heart disease in adults aged 40-79 years in Germany: results of the German Health Interview and Examination Survey for Adults (DEGS1)].
Dermatitis, Atopic
Current status of allergy prevalence in Germany: Position paper of the Environmental Medicine Commission of the Robert Koch Institute.
Dermatitis, Contact
Current status of allergy prevalence in Germany: Position paper of the Environmental Medicine Commission of the Robert Koch Institute.
Food Hypersensitivity
Current status of allergy prevalence in Germany: Position paper of the Environmental Medicine Commission of the Robert Koch Institute.
Hypersensitivity
Current status of allergy prevalence in Germany: Position paper of the Environmental Medicine Commission of the Robert Koch Institute.
Hypertension
Ceramide mediates vascular dysfunction in diet-induced obesity by PP2A-mediated dephosphorylation of the eNOS-Akt complex.
Hypertension
Comparing nationwide prevalences of hypertension and depression based on claims data and survey data: An example from Germany.
Hypertension
How to compare cardiovascular disease and risk factors in elderly patients with haemophilia with the general population.
Hypertension
[Blood pressure in Germany 2008-2011: results of the German Health Interview and Examination Survey for Adults (DEGS1)].
Infection
Dihydrosphingomyelin impairs HIV-1 infection by rigidifying liquid-ordered membrane domains.
Infertility, Male
The Des-1 protein, required for central spindle assembly and cytokinesis, is associated with mitochondria along the meiotic spindle apparatus and with the contractile ring during male meiosis in Drosophila melanogaster.
Influenza, Human
[Vaccination coverage in German adults: results of the German Health Interview and Examination Survey for Adults (DEGS1)].
Insulin Resistance
Differential regulation of Dihydroceramide desaturase by palmitate vs. monounsaturated fatty acids:Implications to insulin resistance.
Insulin Resistance
Mechanistic interplay between ceramide and insulin resistance.
Metabolic Diseases
Ablation of dihydroceramide desaturase 1, a therapeutic target for the treatment of metabolic diseases, simultaneously stimulates anabolic and catabolic signaling.
Myocardial Infarction
[Prevalence of myocardial infarction and coronary heart disease in adults aged 40-79 years in Germany: results of the German Health Interview and Examination Survey for Adults (DEGS1)].
Neoplasm Metastasis
Overexpression of degenerative spermatocyte homolog 1 up-regulates the expression of cyclin D1 and enhances metastatic efficiency in esophageal carcinoma Eca109 cells.
Neoplasms
Alkaline ceramidase 2 (ACER2) and its product dihydrosphingosine mediate the cytotoxicity of N-(4-hydroxyphenyl)retinamide in tumor cells.
Neoplasms
Cationic ceramides and analogues, LCL30 and LCL85, as adjuvants to photodynamic therapy of tumors.
Neoplasms
Dihydroceramide desaturase activity in tumors.
Neoplasms
Overexpression of degenerative spermatocyte homolog 1 up-regulates the expression of cyclin D1 and enhances metastatic efficiency in esophageal carcinoma Eca109 cells.
Neoplasms
[Participation in cancer screening in Germany: results of the German Health Interview and Examination Survey for Adults (DEGS1)].
Neuroblastoma
Cell density dependent reduction of dihydroceramide desaturase activity in neuroblastoma cells.
Neuroblastoma
Involvement of dihydroceramide desaturase in cell cycle progression in human neuroblastoma cells.
Obesity
Increased dihydroceramide/ceramide ratio mediated by defective expression of degs1 impairs adipocyte differentiation and function.
Obesity
[Overweight and obesity in Germany: results of the German Health Interview and Examination Survey for Adults (DEGS1)].
Prostatic Neoplasms
Proteasomal degradation of sphingosine kinase 1 and inhibition of dihydroceramide desaturase by the sphingosine kinase inhibitors, SKi or ABC294640, induces growth arrest in androgen-independent LNCaP-AI prostate cancer cells.
Prostatic Neoplasms
The Sphingosine Kinase 2 Inhibitor ABC294640 Reduces the Growth of Prostate Cancer Cells and Results in Accumulation of Dihydroceramides In Vitro and In Vivo.
Renal Insufficiency
The Prevalence of Renal Failure.
Rhinitis, Allergic, Seasonal
Current status of allergy prevalence in Germany: Position paper of the Environmental Medicine Commission of the Robert Koch Institute.
Sarcoma
Dihydroceramide desaturase activity in tumors.
Stroke
[Prevalence of stroke in adults aged 40 to 79 years in Germany: results of the German Health Interview and Examination Survey for Adults (DEGS1)].
Thrombosis
Comparison of the safety between first- and second-generation drug eluting stents Meta-analysis from 19 randomized trials and 16,924 patients.
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Beauchamp, E.; Goenaga, D.; Le Bloch, J.; Catheline, D.; Legrand, P.; Rioux, V.
Myristic acid increases the activity of dihydroceramide DELTA4-desaturase 1 through its N-terminal myristoylation
Biochimie
89
1553-1561
2007
Rattus norvegicus (Q5XIF5)
brenda
Beauchamp, E.; Tekpli, X.; Marteil, G.; Lagadic-Gossmann, D.; Legrand, P.; Rioux, V.
N-myristoylation targets dihydroceramide DELTA4-desaturase 1 to mitochondria: Partial involvement in the apoptotic effect of myristic acid
Biochimie
91
1411-1419
2009
Rattus norvegicus (Q564G3)
brenda
Garton, S.; Michaelson, L.V.; Beaudoin, F.; Beale, M.H.; Napier, J.A.
The dihydroceramide desaturase is not essential for cell viability in Schizosaccharomyces pombe
FEBS Lett.
538
192-196
2003
Schizosaccharomyces pombe (O59715), Schizosaccharomyces pombe
brenda
Michel, C.; Van Echten-Deckert, G.; Rother, J.; Sandhoff, K.; Wang, E.; Merrill Jr., A.
Characterization of ceramide synthesis. A dihydroceramide desaturase introduces the 4,5-trans-double bond of sphingosine at the level of dihydroceramide
J. Biol. Chem.
272
22432-22437
1997
Rattus norvegicus (Q564G3)
brenda
Ternes, P.; Franke, S.; Zaehringer, U.; Sperling, P.; Heinz, E.
Identification and characterization of a sphingolipid delta 4-desaturase family
J. Biol. Chem.
277
25512-25518
2002
Caenorhabditis elegans (G5EC63), Candida albicans, Candida albicans (Q5AJX2), Drosophila melanogaster, Drosophila melanogaster (Q94515), Homo sapiens, Homo sapiens (O15121), Mus musculus, Mus musculus (O09005)
brenda
Ternes, P.; Wobbe, T.; Schwarz, M.; Albrecht, S.; Feussner, K.; Riezman, I.; Cregg, J.; Heinz, E.; Riezman, H.; Feussner, I.; Warnecke, D.
Two pathways of sphingolipid biosynthesis are separated in the yeast Pichia pastoris
J. Biol. Chem.
286
11401-11414
2011
Komagataella pastoris
brenda
Causeret, C.; Geeraert, L.; Van der Hoeven, G.; Mannaerts, G.; Van Veldhoven, P.
Further characterization of rat dihydroceramide desaturase: Tissue distribution, subcellular localization, and substrate specificity
Lipids
35
1117-1125
2000
Rattus norvegicus (Q564H3)
brenda
Ezanno, H.; Le Bloch, J.; Beauchamp, E.; Lagadic-Gossmann, D.; Legrand, P.; Rioux, V.
Myristic acid increases dihydroceramide DELTA4-desaturase 1 (DES1) activity in cultured rat hepatocytes
Lipids
47
117-128
2012
Rattus norvegicus (Q564G3)
brenda
Beckmann, C.; Rattke, J.; Sperling, P.; Heinz, E.; Boland, W.
Stereochemistry of a bifunctional dihydroceramide DELTA4-desaturase/hydroxylase from Candida albicans; a key enzyme of sphingolipid metabolism
Org. Biomol. Chem.
1
2448-2454
2003
Candida albicans
brenda
Luttgeharm, K.; Kimberlin, A.; Cahoon, R.; Cerny, R.; Napier, J.; Markham, J.; Cahoon, E.
Sphingolipid metabolism is strikingly different between pollen and leaf in Arabidopsis as revealed by compositional and gene expression profiling
Phytochemistry
115
121-129
2015
Arabidopsis thaliana
brenda
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