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Information on EC 2.3.1.297 - very-long-chain ceramide synthase
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2.3.1.297 very-long-chain ceramide synthaseIUBMB Comments
This entry describes ceramide synthase enzymes that are specific for very-long-chain fatty acyl-CoA substrates. The two isoforms from yeast and the plant LOH1 and LOH3 isoforms transfer 24:0 and 26:0 acyl chains preferentially and use phytosphingosine as the preferred sphingoid base. The mammalian CERS2 isoform is specific for acyl donors of 20-26 carbons, which can be saturated or unsaturated. The mammalian CERS3 isoform catalyses this activity, but has a broader substrate range and also catalyses the activity of EC 2.3.1.298, ultra-long-chain ceramide synthase. Both mammalian enzymes can use multiple sphingoid bases, including sphinganine, sphingosine, and phytosphingosine.
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Word Map
- 2.3.1.297
- sphingolipids
- sphingomyelins
- dihydroceramide
-
cers1-6
- elovl1
- pnpla1
- cyp4f22
- alox12b
-
sdr9c7
-
nipal4
-
abca12
-
cerss
- aloxe3
- diagnostics
The enzyme appears in viruses and cellular organisms
Reaction Schemes
a very-long-chain fatty acyl-CoA
+
=
a very-long-chain ceramide
+
Synonyms
cers2, lass2, cers3, ceramide synthase 2, ceramide synthase 3, lass4, lass3, longevity assurance homologue 2, lag13, ceramide synthase complex, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
acyl-CoA : sphingosine N-acyltramferase
acyl-CoA ceramide synthase
ceramide synthase
ceramide synthase 2
ceramide synthase 4
ceramide synthase complex
CerS2
CerS3
CerS4
LAC1
-
-
-
-
Lac1p/Lag1p
LAG1
-
-
-
-
Lass2
LASS3
Lass4
LOH1
LOH3
mammalian ceramide synthase 2
-
-
-
-
sphingoid base N-very-long-chain fatty acyl-coA transferase
-
-
-
-
additional information
ceramide synthase 2
-
CerS3
-
-
-
-
LASS3
-
-
-
-
LOH1
-
-
-
-
LOH3
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a very-long-chain fatty acyl-CoA + a sphingoid base = a very-long-chain ceramide + CoA
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
very-long-chain fatty acyl-coA:sphingoid base N-acyltransferase
This entry describes ceramide synthase enzymes that are specific for very-long-chain fatty acyl-CoA substrates. The two isoforms from yeast and the plant LOH1 and LOH3 isoforms transfer 24:0 and 26:0 acyl chains preferentially and use phytosphingosine as the preferred sphingoid base. The mammalian CERS2 isoform is specific for acyl donors of 20-26 carbons, which can be saturated or unsaturated. The mammalian CERS3 isoform catalyses this activity, but has a broader substrate range and also catalyses the activity of EC 2.3.1.298, ultra-long-chain ceramide synthase. Both mammalian enzymes can use multiple sphingoid bases, including sphinganine, sphingosine, and phytosphingosine.
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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 very-long-chain fatty acyl-CoA + sphinganine
a very-long-chain sphinganine + CoA
-
-
-
-
?
acyl-CoA + sphinganine
N-acylsphinganine + CoA
very low activity with sphinganine
-
-
?
behenoyl-CoA + dihydrosphingosine
CoA + N-behenoyldihydrosphingosine
-
-
-
?
dihydrosphingosine + palmitoyl-CoA
N-palmitoyldihydrosphingosine + CoA
low activity
-
-
?
dihydrosphingosine + stearoyl-CoA
N-stearoyldihydrosphingosine + CoA
low activity
-
-
?
hexacosanoyl-CoA + phytosphingosine
CoA + N-hexacosanoylphytosphingosine
-
-
-
?
hexacosenoyl-CoA + a sphingoid base
hexacosenoyl ceramide + CoA
-
-
-
-
?
nervonyl-CoA + a sphingoid base
nervonyl ceramide + CoA
-
-
-
-
?
sphingosine + 2-hydroxybehenoyl-CoA
N-2-hydroxybehenoylsphingosine + CoA
-
-
-
?
sphingosine + 2-hydroxyeicosanoyl-CoA
N-2-hydroxyeicosanoylsphingosine + CoA
-
-
-
?
sphingosine + 2-hydroxylignoceroyl-CoA
N-2-hydroxylignoceroylsphingosine + CoA
-
-
-
?
sphingosine + arachidoyl-CoA
N-arachidoylsphingosine + CoA
low activity
-
-
?
sphingosine + eicosanoyl-CoA
N-eicosanoylsphingosine + CoA
-
-
-
?
sphingosine + hexacosanoyl-CoA
N-hexacosanoylsphingosine + CoA
low activity
-
-
?
a very-long-chain fatty acyl-CoA + a sphingoid base
a very-long-chain ceramide + CoA
-
-
-
-
?
a very-long-chain fatty acyl-CoA + a sphingoid base
a very-long-chain ceramide + CoA
-
-
-
-
?
a very-long-chain fatty acyl-CoA + a sphingoid base
a very-long-chain ceramide + CoA
-
the enzyme synthesizes ceramides with very-long (C22-C24) acyl chains
-
-
?
D-erythro-sphinganine + arachidoyl-CoA
N-arachidoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + arachidoyl-CoA
N-arachidoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + arachidoyl-CoA
N-arachidoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + arachidoyl-CoA
N-arachidoyl-D-sphinganine + CoA
Saccharomyces cerevisiae RH4838
-
-
-
?
D-erythro-sphinganine + behenoyl-CoA
N-behenoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + behenoyl-CoA
N-behenoyl-D-sphinganine + CoA
preferred substrate
-
-
?
D-erythro-sphinganine + behenoyl-CoA
N-behenoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + cerotoyl-CoA
N-cerotoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + cerotoyl-CoA
N-cerotoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + cerotoyl-CoA
N-cerotoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + cerotoyl-CoA
N-cerotoyl-D-sphinganine + CoA
Saccharomyces cerevisiae RH4838
-
-
-
?
D-erythro-sphinganine + lignoceroyl-CoA
N-lignoceroyl-D-sphinganine + CoA
-
-
-
-
?
D-erythro-sphinganine + lignoceroyl-CoA
N-lignoceroyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + lignoceroyl-CoA
N-lignoceroyl-D-sphinganine + CoA
-
-
-
-
?
D-erythro-sphinganine + lignoceroyl-CoA
N-lignoceroyl-D-sphinganine + CoA
preferred substrate
-
-
?
D-erythro-sphinganine + lignoceroyl-CoA
N-lignoceroyl-D-sphinganine + CoA
-
-
-
-
?
D-erythro-sphinganine + nervonoyl-CoA
N-nervonoyl-D-sphinganine + CoA
-
-
-
?
dihydrosphingosine + lignoceroyl-CoA
N-lignoceroyldihydrosphingosine + CoA
-
-
-
?
dihydrosphingosine + lignoceroyl-CoA
N-lignoceroyldihydrosphingosine + CoA
low activity
-
-
?
dihydrosphingosine + nervonoyl-CoA
N-nervonoyldihydrosphingosine + CoA
-
-
-
?
dihydrosphingosine + nervonoyl-CoA
N-nervonoyldihydrosphingosine + CoA
highly preferred substrate
-
-
?
DL-erythro-sphingosine + nervonoyl-CoA
N-nervonoylsphingosine + CoA
-
both the threo and erythro isomers are active as acceptors, the latter is preferred
-
-
?
DL-erythro-sphingosine + nervonoyl-CoA
N-nervonoylsphingosine + CoA
-
both the threo and erythro isomers are active as acceptors, the latter is preferred
-
-
?
DL-threo-sphingosine + nervonoyl-CoA
N-nervonoylsphingosine + CoA
-
both the threo and erythro isomers are active as acceptors, the latter is preferred
-
-
?
DL-threo-sphingosine + nervonoyl-CoA
N-nervonoylsphingosine + CoA
-
both the threo and erythro isomers are active as acceptors, the latter is preferred
-
-
?
lignoceroyl-CoA + phytosphingosine
N-lignoceroylphytosphinganine + CoA
-
-
-
?
lignoceroyl-CoA + phytosphingosine
N-lignoceroylphytosphinganine + CoA
high activity
-
-
?
nervonoyl-CoA + NBD-sphinganine
CoA + N-nervonoyl-NBD-sphinganine
C24:1-CoA substrate and NBD-labeled sphinganine substrate, i.e. omega(7-nitro-2-1,3-benzoxadiazole-4-yl)(2S,3R)-2-aminooctadecane-1,3-diol
-
-
?
nervonoyl-CoA + NBD-sphinganine
CoA + N-nervonoyl-NBD-sphinganine
C24:1-CoA substrate and NBD-labeled sphinganine substrate, i.e. omega(7-nitro-2-1,3-benzoxadiazole-4-yl)(2S,3R)-2-aminooctadecane-1,3-diol
-
-
?
sphinganine + arachidoyl-CoA
N-arachidoylsphinganine + CoA
low activity
-
-
?
sphinganine + behenoyl-CoA
N-behenoylsphinganine + CoA
moderate activity
-
-
?
sphinganine + cerotoyl-CoA
N-cerotoylsphinganine + CoA
low activity
-
-
?
sphinganine + cerotoyl-CoA
N-cerotoylsphinganine + CoA
low activity
-
-
?
sphinganine + lignoceroyl-CoA
N-lignoceroylsphinganine + CoA
-
-
-
?
sphinganine + lignoceroyl-CoA
N-lignoceroylsphinganine + CoA
high activity
-
-
?
sphinganine + palmitoyl-CoA
N-palmitoylsphinganine + CoA
low activity
-
-
?
sphinganine + stearoyl-CoA
N-stearoylsphinganine + CoA
preferred substrate
-
-
?
sphingosine + lignoceroyl-CoA
N-lignoceroylsphingosine + CoA
-
-
-
?
sphingosine + lignoceroyl-CoA
N-lignoceroylsphingosine + CoA
-
-
-
?
sphingosine + stearoyl-CoA
N-stearoylsphingosine + CoA
low activity
-
-
?
additional information
?
-
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. LOH3 has at least twice as much activity with t18:1 substrates as LOH1. Both LOH1 and LOH3 demonstrate a strong preference for very long chain acyl-CoAs (>C18) although LOH1 has the greatest activity toward 24 and 26 carbon acyl-CoAs, while LOH3 shows little preference for acyl-CoAs between 20 and 26 carbons in length
-
-
?
additional information
?
-
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. LOH3 has at least twice as much activity with t18:1 substrates as LOH1. Both LOH1 and LOH3 demonstrate a strong preference for very long chain acyl-CoAs (>C18) although LOH1 has the greatest activity toward 24 and 26 carbon acyl-CoAs, while LOH3 shows little preference for acyl-CoAs between 20 and 26 carbons in length
-
-
?
additional information
?
-
CERS2 preferentially transfers very long chain fatty acids (C22-C26)
-
-
?
additional information
?
-
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
-
-
?
additional information
?
-
CERS2 preferentially transfers very long chain fatty acids (C22:0-C26:0) to dihydrosphingosine. Improvement of a fluorescent assay, using HPLC using C16:0, C18:0 and C24:1 fatty acids and commercially available sphinganine-NBD, i.e. 7-nitro-2-1,3-benzoxadiazole-labelled dihydrosphingosine or (2S,3R)-2-amino-18((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)octadecane-1-3-diol, as substrates, very accurate and sensitive method for quantification of CERS activity, method evaluation
-
-
?
additional information
?
-
substrate specificity, overview. Long-chain preference of CerS2
-
-
?
additional information
?
-
substrate specificity, overview. Long-chain preference of CerS2
-
-
?
additional information
?
-
ceramide synthase 2 catalyzes the synthesis of dihydroceramides from dihydrosphingosine and very long fatty acyl (C22-C24)-CoAs
-
-
?
additional information
?
-
-
ceramide synthase 2 catalyzes the synthesis of dihydroceramides from dihydrosphingosine and very long fatty acyl (C22-C24)-CoAs
-
-
?
additional information
?
-
both C22:0- and C24:0-CoAs are used effectively for Lass2- and Lass4-dependent ceramide synthesis, and C26:0-, C20:0-, and C18:0-CoAs also act as substrates, albeit weakly. Recombinant Lass2 produces longer ceramides such as C22:0 ceramides and C24:0 ceramides in transgenic HEK-293T cells
-
-
?
additional information
?
-
both C22:0- and C24:0-CoAs are used effectively for Lass2- and Lass4-dependent ceramide synthesis, and C26:0-, C20:0-, and C18:0-CoAs also act as substrates, albeit weakly. Recombinant Lass2 produces longer ceramides such as C22:0 ceramides and C24:0 ceramides in transgenic HEK-293T cells
-
-
?
additional information
?
-
-
both C22:0- and C24:0-CoAs are used effectively for Lass2- and Lass4-dependent ceramide synthesis, and C26:0-, C20:0-, and C18:0-CoAs also act as substrates, albeit weakly. Recombinant Lass2 produces longer ceramides such as C22:0 ceramides and C24:0 ceramides in transgenic HEK-293T cells
-
-
?
additional information
?
-
both C22:0- and C24:0-CoAs are used effectively for Lass2- and Lass4-dependent ceramide synthesis, and C26:0-, C20:0-, and C18:0-CoAs also act as substrates, albeit weakly. Recombinant Lass4 produces longer ceramides such as C22:0 and C24:0 ceramides in transgenic HEK-293T cells
-
-
?
additional information
?
-
both C22:0- and C24:0-CoAs are used effectively for Lass2- and Lass4-dependent ceramide synthesis, and C26:0-, C20:0-, and C18:0-CoAs also act as substrates, albeit weakly. Recombinant Lass4 produces longer ceramides such as C22:0 and C24:0 ceramides in transgenic HEK-293T cells
-
-
?
additional information
?
-
-
both C22:0- and C24:0-CoAs are used effectively for Lass2- and Lass4-dependent ceramide synthesis, and C26:0-, C20:0-, and C18:0-CoAs also act as substrates, albeit weakly. Recombinant Lass4 produces longer ceramides such as C22:0 and C24:0 ceramides in transgenic HEK-293T cells
-
-
?
additional information
?
-
CerS2 can utilize a wider range of fatty acyl-CoAs but uses mainly C22 to C24
-
-
?
additional information
?
-
-
CerS2 can utilize a wider range of fatty acyl-CoAs but uses mainly C22 to C24
-
-
?
additional information
?
-
CerS2 has a remarkable acyl-CoA specificity, it uses a wider range of acyl-CoAs, synthesizing ceramides containing C20:0, C22:0, C24:1, C24:0, C26:1, and C26:0 fatty acids, but does not synthesize ceramides containing C16:0 fatty acids and synthesizes only low, and statistically insignificant levels of C18:0-ceramide, overview
-
-
?
additional information
?
-
enzyme LASS3 shows a relatively broad substrate specificity. Both LASS3 isoforms increase the production of several ceramide species, including C18:0- and C24:0-ceramides. LASS3 exhibits relatively low substrate specificity toward fatty acyl-CoAs. Lysates prepared from LASS3-overproducing cells show significant activity toward several fatty acyl-CoAs, including C18:0-, C22:0-, and C24:0-CoA, with the highest activity for C18:0. C16:0-, C20:0-, and C26:0-CoA are also used as substrates by LASS3, albeit with low activity. LASS3-overproducing cells synthesize ceramide from C18:0-CoA with the highest activity at all concentrations tested. This in vitro result is quite consistent with the in vivo results
-
-
?
additional information
?
-
-
enzyme LASS3 shows a relatively broad substrate specificity. Both LASS3 isoforms increase the production of several ceramide species, including C18:0- and C24:0-ceramides. LASS3 exhibits relatively low substrate specificity toward fatty acyl-CoAs. Lysates prepared from LASS3-overproducing cells show significant activity toward several fatty acyl-CoAs, including C18:0-, C22:0-, and C24:0-CoA, with the highest activity for C18:0. C16:0-, C20:0-, and C26:0-CoA are also used as substrates by LASS3, albeit with low activity. LASS3-overproducing cells synthesize ceramide from C18:0-CoA with the highest activity at all concentrations tested. This in vitro result is quite consistent with the in vivo results
-
-
?
additional information
?
-
CerS2 has a remarkable acyl-CoA specificity, it uses a wider range of acyl-CoAs, synthesizing ceramides containing C20:0, C22:0, C24:1, C24:0, C26:1, and C26:0 fatty acids, but does not synthesize ceramides containing C16:0 fatty acids and synthesizes only low, and statistically insignificant levels of C18:0-ceramide, overview
-
-
?
additional information
?
-
ceramide synthase 2 catalyzes the synthesis of dihydroceramides from dihydrosphingosine and very long fatty acyl (C22-C24)-CoAs
-
-
?
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NATURAL SUBSTRATE
NATURAL 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 very-long-chain fatty acyl-CoA + sphinganine
a very-long-chain sphinganine + CoA
-
-
-
-
?
behenoyl-CoA + dihydrosphingosine
CoA + N-behenoyldihydrosphingosine
-
-
-
?
dihydrosphingosine + lignoceroyl-CoA
N-lignoceroyldihydrosphingosine + CoA
-
-
-
?
dihydrosphingosine + nervonoyl-CoA
N-nervonoyldihydrosphingosine + CoA
-
-
-
?
hexacosanoyl-CoA + phytosphingosine
CoA + N-hexacosanoylphytosphingosine
-
-
-
?
lignoceroyl-CoA + phytosphingosine
N-lignoceroylphytosphinganine + CoA
-
-
-
?
sphingosine + eicosanoyl-CoA
N-eicosanoylsphingosine + CoA
-
-
-
?
a very-long-chain fatty acyl-CoA + a sphingoid base
a very-long-chain ceramide + CoA
-
-
-
-
?
a very-long-chain fatty acyl-CoA + a sphingoid base
a very-long-chain ceramide + CoA
-
-
-
-
?
a very-long-chain fatty acyl-CoA + a sphingoid base
a very-long-chain ceramide + CoA
-
the enzyme synthesizes ceramides with very-long (C22-C24) acyl chains
-
-
?
D-erythro-sphinganine + arachidoyl-CoA
N-arachidoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + arachidoyl-CoA
N-arachidoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + arachidoyl-CoA
N-arachidoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + arachidoyl-CoA
N-arachidoyl-D-sphinganine + CoA
Saccharomyces cerevisiae RH4838
-
-
-
?
D-erythro-sphinganine + behenoyl-CoA
N-behenoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + behenoyl-CoA
N-behenoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + cerotoyl-CoA
N-cerotoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + cerotoyl-CoA
N-cerotoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + cerotoyl-CoA
N-cerotoyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + cerotoyl-CoA
N-cerotoyl-D-sphinganine + CoA
Saccharomyces cerevisiae RH4838
-
-
-
?
D-erythro-sphinganine + lignoceroyl-CoA
N-lignoceroyl-D-sphinganine + CoA
-
-
-
-
?
D-erythro-sphinganine + lignoceroyl-CoA
N-lignoceroyl-D-sphinganine + CoA
-
-
-
?
D-erythro-sphinganine + lignoceroyl-CoA
N-lignoceroyl-D-sphinganine + CoA
-
-
-
-
?
D-erythro-sphinganine + lignoceroyl-CoA
N-lignoceroyl-D-sphinganine + CoA
-
-
-
-
?
D-erythro-sphinganine + nervonoyl-CoA
N-nervonoyl-D-sphinganine + CoA
-
-
-
?
sphinganine + cerotoyl-CoA
N-cerotoylsphinganine + CoA
low activity
-
-
?
sphinganine + lignoceroyl-CoA
N-lignoceroylsphinganine + CoA
-
-
-
?