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Information on EC 2.3.1.24 - sphingosine N-acyltransferase
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2.3.1.24 sphingosine N-acyltransferaseIUBMB Comments
Acts on sphingosine or its 2-epimer.
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Word Map
- 2.3.1.24
- sphingolipids
- fumonisins
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sphingoid
- synthases
- sphingomyelin
- sphingomyelinase
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mycotoxin
- fusarium
- palmitoyltransferase
- dihydroceramide
- glucosylceramide
- verticillioides
- ceramidase
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n-acylation
- moniliforme
- sphingosine-1-phosphate
- myriocin
- glycosphingolipids
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llc-pk1
- phytosphingosine
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fb1-induced
- c16-ceramide
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corn-based
- medicine
- smases
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very-long-chain
- analysis
- fenretinide
- glccers
- dihydrosphingosine
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ceramide-induced
- diagnostics
- l-cycloserine
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acyl-coa-dependent
The enzyme appears in viruses and cellular organisms
Synonyms
ceramide synthase, cers6, cers5, cers4, lass5, ceramide synthase 6, lass6, ceramide synthase 5, sphinganine n-acyltransferase, (dihydro)ceramide synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(dihydro)ceramide synthase
acyl-CoA : sphingosine N-acyltramferase
acyl-CoA : sphingosine N-acyltransferase
acyltransferase, sphingosine
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ceramide synthase
ceramide synthase 4
ceramide synthase 5
ceramide synthase 6
ceramide synthetase
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CerS4
CerS5
CerS6
LAG1
LASS5
Lass6
longevity assurance homolog 5
sphinganine N-acyl transferase synthase
sphinganine N-acyltransferase
sphingosine acyltransferase
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sphingosine N-acyltransferase
sphingosine/sphinganine acyltransferase
additional information
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
an acyl-CoA + sphingosine = CoA + a ceramide
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Acyl group transfer
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
acyl-CoA:sphingosine N-acyltransferase
Acts on sphingosine or its 2-epimer.
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CAS REGISTRY NUMBER
COMMENTARY
37257-09-3
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
a fatty acyl-CoA + phytosphingosine
CoA + an N-acylphytosphingosine
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?
acyl-CoA + sphingosine
?
LASS5 is the major ceramide synthase gene product involved in sphingolipid production that may also regulate PtdCho metabolism in pulmonary epithelia
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?
dihydrosphingosine + myristoyl-CoA
N-myristoyldihydrosphingosine + CoA
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?
dihydrosphingosine + stearoyl-CoA
N-stearoyldihydrosphingosine + CoA
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?
DL-erythro-sphingosine + palmitoyl-CoA
N-palmitoylsphingosine + CoA
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both the threo and erythro isomers are active as acceptors, the latter is preferred
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?
DL-threo-sphingosine + palmitoyl-CoA
N-palmitoyl-DL-sphingosine + CoA
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both the threo and erythro isomers are active as acceptors, the latter is slightly preferred
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?
DL-threo-sphingosine + palmitoyl-CoA
N-palmitoylsphingosine + CoA
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both the threo and erythro isomers are active as acceptors, the latter is preferred
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?
docosanoyl-CoA + sphingosine
CoA + N-docosanoylsphingosine
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?
eicosanoyl-CoA + sphingosine
CoA + N-eicosanoylsphingosine
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?
fatty acyl-CoA + dihydrosphingosine
CoA + an N-acyldihydrosphingosine
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?
hexacosanoyl-CoA + sphingosine
CoA + N-hexacosanoylsphingosine
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?
palmitoyl-CoA + dihydrosphingosine
CoA + N-palmitoyldihydrosphingosine
no reverse ceramidase activity is detected in Trypanosoma cruzi microsomal fractions
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?
sphinganine + arachidoyl-CoA
N-arachidoylsphinganine + CoA
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?
sphinganine + stearoyl-CoA
N-stearoyl-DL-dihydrosphingosine + CoA
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i.e. DL-erythro-2-amino-1,3-octadecanediol
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?
sphingosine + 2-hydroxy-palmitoyl-CoA
N-2-hydroxy-palmitoyl-sphingosine + CoA
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?
sphingosine + eicosanoyl-CoA
N-eicosanoylsphingosine + CoA
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?
sphingosine + hexanoyl-CoA
N-hexanoylsphingosine + CoA
very low activity
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?
stearoyl-CoA + phytosphingosine
CoA + N-stearoylphytosphingosine
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?
acyl-CoA + phytosphingosine
CoA + N-acylphytosphingosine
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?
acyl-CoA + phytosphingosine
CoA + N-acylphytosphingosine
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?
D-erythro-sphinganine + palmitoyl-CoA
N-palmitoyl-D-sphinganine
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low activity
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?
D-erythro-sphinganine + palmitoyl-CoA
N-palmitoyl-D-sphinganine
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low activity
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?
dihydrosphingosine + palmitoyl-CoA
N-palmitoyldihydrosphingosine + CoA
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?
dihydrosphingosine + palmitoyl-CoA
N-palmitoyldihydrosphingosine + CoA
best substrate
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?
DL-erythro-sphingosine + arachidonoyl-CoA
N-arachidonoyl-DL-sphingosine + CoA
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i.e. trans-D-erythro-2-amino-4-octadecene-1,3-diol
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?
DL-erythro-sphingosine + arachidonoyl-CoA
N-arachidonoyl-DL-sphingosine + CoA
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i.e. trans-D-erythro-2-amino-4-octadecene-1,3-diol
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?
DL-erythro-sphingosine + palmitoyl-CoA
N-palmitoyl-DL-sphingosine + CoA
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both the threo and erythro isomers are active as acceptors, the latter is slightly preferred
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?
DL-erythro-sphingosine + palmitoyl-CoA
N-palmitoyl-DL-sphingosine + CoA
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i.e. trans-D-erythro-2-amino-4-octadecene-1,3-diol
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?
DL-erythro-sphingosine + palmitoyl-CoA
N-palmitoyl-DL-sphingosine + CoA
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i.e. trans-D-erythro-2-amino-4-octadecene-1,3-diol
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?
DL-erythro-sphingosine + stearoyl-CoA
N-stearoyl-DL-sphingosine + CoA
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i.e. trans-D-erythro-2-amino-4-octadecene-1,3-diol
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?
DL-erythro-sphingosine + stearoyl-CoA
N-stearoyl-DL-sphingosine + CoA
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i.e. trans-D-erythro-2-amino-4-octadecene-1,3-diol
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?
palmitoyl-CoA + sphingosine
CoA + N-palmitoylsphingosine
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?
palmitoyl-CoA + sphingosine
CoA + N-palmitoylsphingosine
no reverse ceramidase activity is detected in Trypanosoma cruzi microsomal fractions
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?
palmitoyl-CoA + sphingosine
CoA + palmitoylsphingosine
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?
sphinganine + arachidonoyl-CoA
N-arachidonoyl-DL-dihydrosphingosine + CoA
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i.e. DL-erythro-2-amino-1,3-octadecanediol
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?
sphinganine + arachidonoyl-CoA
N-arachidonoyl-DL-dihydrosphingosine + CoA
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i.e. DL-erythro-2-amino-1,3-octadecanediol
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?
sphinganine + palmitoyl-CoA
N-palmitoyl-DL-dihydrosphingosine + CoA
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?
sphinganine + palmitoyl-CoA
N-palmitoyl-DL-dihydrosphingosine + CoA
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i.e. DL-erythro-2-amino-1,3-octadecanediol
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?
sphinganine + palmitoyl-CoA
N-palmitoyl-DL-dihydrosphingosine + CoA
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i.e. DL-erythro-2-amino-1,3-octadecanediol
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?
sphingosine + behenoyl-CoA
N-behenoylsphingosine + CoA
low activity
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?
sphingosine + lauroyl-CoA
N-lauroylsphingosine + CoA
very low activity
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?
sphingosine + lauroyl-CoA
N-lauroylsphingosine + CoA
low activity
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?
sphingosine + oleoyl-CoA
N-oleoylsphingosine + CoA
low activity
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?
sphingosine + palmitoyl-CoA
N-palmitoylsphingosine + CoA
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?
sphingosine + stearoyl-CoA
N-stearoylsphingosine + CoA
low activity
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?
stearoyl-CoA + sphingosine
CoA + N-stearoylsphingosine
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?
stearoyl-CoA + sphingosine
CoA + N-stearoylsphingosine
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tetracosanoyl-CoA + sphingosine
CoA + N-tetracosanoylsphingosine
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?
additional information
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specificity of three different isoforms of ceramide synthase, denoted LOH1, 2 and 3, for a range of long-chain base (LCB) and acyl-CoA substrates. The contribution of each of these isoforms to the synthesis of ceramide is investigated by in vitro ceramide synthase assays, overview. The plant LCB phytosphingosine is efficiently used by the LOH1 and 3 isoforms, with LOH1 having the lowest Km for the LCB substrate of the three isoforms. In contrast, sphinganine is used efficiently only by the LOH2 isoform. Acyl-CoA specificity is also distinguished between the three isoforms with LOH2 being almost completely specific for palmitoyl-CoA, while the LOH1 isoform shows greatest activity with lignoceroyl- and hexacosanoyl-CoA. Unsaturated acyl-CoAs are not used efficiently by any isoform while unsaturated LCB substrates are preferred by LOH2 and 3. LOH2 shows poor activity with phytosphingosine. LOH2 is unable to use any acyl-CoA substrates greater than C18 and shows very strong preference for C16 acyl-CoA. Recombinant LOH2 shows maximum activity with the d18:1(4E) LCB about 6 times that with the d18:0 LCB, eventhough d18:1(4E) is not observed in Arabidopsis leaves. Rather d18:2(4E/8Z) or d18:2(4E/8E) are found in selected tissues such as pollen. LOH2 shows enhanced activity towards DELTA4 unsaturated LCB substrates
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additional information
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substrate specificity of the purified enzyme is determined with various acyl (C6-C22)-CoA and sphingosine or with stearoyl-CoA and sphinganine as substrates. CoA esters having regular chain (C16-C18) are good substrates. Very long chain (C22) or short chain (C6-C12) show low activity
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additional information
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substrate specificity of the purified enzyme is determined with various acyl (C6-C22)-CoA and sphingosine or with stearoyl-CoA and sphinganine as substrates. CoA esters having regular chain (C16-C18) are good substrates. Very long chain (C22) or short chain (C6-C12) show low activity
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additional information
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the enzyme is also active with longer-chain acyl-CoAs. Substrate preparation, overview. Usage of radiolabeled, or fluorescent substrates
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additional information
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isoform Cer1 shows a clear preference for C18 fatty acyl CoA and sphingosine as a substrate
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additional information
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isoform Cer1 shows a clear preference for C18 fatty acyl CoA and sphingosine as a substrate
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additional information
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isoform Cer1 shows a clear preference for C18 fatty acyl CoA and sphingosine as a substrate
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additional information
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CERS5 transfers C16 fatty acids, and potentially also C14 and C18 fatty acids
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?
additional information
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CERS5 transfers C16 fatty acids, and potentially also C14 and C18 fatty acids
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additional information
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CERS5 transfers C16 fatty acids, and potentially also C14 and C18 fatty acids
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?
additional information
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CerS6 lysate produces nonhydroxy-dihydro-ceramides that included strong bands for C14:0- and C16:0-dihydro-ceramide, but a weak band for C18:0-dihydro-ceramide
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additional information
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CerS6 lysate produces nonhydroxy-dihydro-ceramides that included strong bands for C14:0- and C16:0-dihydro-ceramide, but a weak band for C18:0-dihydro-ceramide
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additional information
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CERS activity is assayed using LC-MS/MS for product quantification, crude extracts containing cell membranes are firstly prepared from tissues or cultured cells, reactions contain deuterated dihydrosphingosine (or sphingosine) and a fatty acid substrate linked to CoA (C16:0 to C24:0/24:1), detailed method descritpion and evaluation, overview
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additional information
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CERS activity is assayed using LC-MS/MS for product quantification, crude extracts containing cell membranes are firstly prepared from tissues or cultured cells, reactions contain deuterated dihydrosphingosine (or sphingosine) and a fatty acid substrate linked to CoA (C16:0 to C24:0/24:1), detailed method descritpion and evaluation, overview
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additional information
?
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CERS activity is assayed using LC-MS/MS for product quantification, crude extracts containing cell membranes are firstly prepared from tissues or cultured cells, reactions contain deuterated dihydrosphingosine (or sphingosine) and a fatty acid substrate linked to CoA (C16:0 to C24:0/24:1), detailed method descritpion and evaluation, overview
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additional information
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expression of CERS3 increases the levels of C18-C22-ceramides, whereas it reduces the levels of C16:0-ceramide and C24-ceramides
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additional information
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expression of CERS3 increases the levels of C18-C22-ceramides, whereas it reduces the levels of C16:0-ceramide and C24-ceramides
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additional information
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expression of CERS3 increases the levels of C18-C22-ceramides, whereas it reduces the levels of C16:0-ceramide and C24-ceramides
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additional information
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expression of CERS3 increases the levels of C18-C22-ceramides, whereas it reduces the levels of C16:0-ceramide and C24-ceramides
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additional information
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expression of CERS3 increases the levels of C18-C22-ceramides, whereas it reduces the levels of C16:0-ceramide and C24-ceramides
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additional information
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expression of CERS3 increases the levels of C26:0-ceramide as well as those of C18:0-ceramide, C20:0-ceramide, and C24:0-ceramide, whereas it reduces the level of C16:0-ceramide
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additional information
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expression of CERS3 increases the levels of C26:0-ceramide as well as those of C18:0-ceramide, C20:0-ceramide, and C24:0-ceramide, whereas it reduces the level of C16:0-ceramide
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additional information
?
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expression of CERS3 increases the levels of C26:0-ceramide as well as those of C18:0-ceramide, C20:0-ceramide, and C24:0-ceramide, whereas it reduces the level of C16:0-ceramide
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additional information
?
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expression of CERS3 increases the levels of C26:0-ceramide as well as those of C18:0-ceramide, C20:0-ceramide, and C24:0-ceramide, whereas it reduces the level of C16:0-ceramide
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additional information
?
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expression of CERS3 increases the levels of C26:0-ceramide as well as those of C18:0-ceramide, C20:0-ceramide, and C24:0-ceramide, whereas it reduces the level of C16:0-ceramide
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