Information on EC 2.3.1.50 - serine C-palmitoyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.3.1.50
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RECOMMENDED NAME
GeneOntology No.
serine C-palmitoyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
palmitoyl-CoA + L-serine = CoA + 3-dehydro-D-sphinganine + CO2
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
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Claisen condensation
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condensation
decarboxylation
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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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sphingolipid biosynthesis (yeast)
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ceramide biosynthesis
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Sphingolipid metabolism
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
palmitoyl-CoA:L-serine C-palmitoyltransferase (decarboxylating)
A pyridoxal-phosphate protein.
CAS REGISTRY NUMBER
COMMENTARY hide
62213-50-7
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
LCB2; ssp. chinensis
UniProt
Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
cv. early profilic straightneck
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
strain GTC97
UniProt
Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
yeasts
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Automatic Mining of ENzyme DAta
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
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the enzyme belongs to the PLP-superfamily and a member of the alpha-oxoamine synthase family (AOS, fold type I)
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
acyl-CoA + L-serine
CoA + ?
show the reaction diagram
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-
-
-
?
arachidoyl-CoA + L-serine
CoA + 2-amino-1-hydroxydocosan-3-one + CO2
show the reaction diagram
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37% activity compared to that with palmitoyl-CoA
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-
?
elaidoyl-CoA + L-serine
CoA + 2-amino-1-hydroxy-trans-11-eicosen-3-one + CO2
show the reaction diagram
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39% activity compared to that with palmitoyl-CoA
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-
?
L-alanine + palmitoyl-CoA
CoA + (2S)-2-aminooctadecan-3-one + CO2
show the reaction diagram
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-
-
-
?
L-alanine + stearoyl-CoA
CoA + (2S)-2-aminoicosan-3-one + CO2
show the reaction diagram
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-
-
-
?
L-serine + palmitoyl-CoA
CoA + 3-dehydro-D-sphinganine + CO2
show the reaction diagram
L-serine + stearoyl-CoA
CoA + (2S)-2-amino-1-hydroxyicosan-3-one + CO2
show the reaction diagram
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-
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-
?
lauroyl-CoA + L-serine
CoA + 2-amino-1-hydroxytetradecan-3-one + CO2
show the reaction diagram
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18% activity compared to that with palmitoyl-CoA
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-
?
myristoleoyl-CoA + L-serine
CoA + 2-amino-1-hydroxy-cis-11-hexadecen-3-one + CO2
show the reaction diagram
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46% activity compared to that with palmitoyl-CoA
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-
?
myristoyl-CoA + L-serine
CoA + 2-amino-1-hydroxy-cis-11-hexadecen-3-one + CO2
show the reaction diagram
myristoyl-CoA + L-serine
CoA + 2-amino-1-hydroxyhexadecan-3-one + CO2
show the reaction diagram
myristoyl-CoA + L-serine
CoA + ? + CO2
show the reaction diagram
n-heptadecanoyl-CoA + L-serine
CoA + 2-amino-1-hydroxynonadecan-3-one + CO2
show the reaction diagram
oleoyl-CoA + L-serine
CoA + 2-amino-1-hydroxy-11-cis-eicosen-3-one + CO2
show the reaction diagram
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57% activity compared to that with palmitoyl-CoA
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?
palmitoleoyl-CoA + L-serine
CoA + 2-amino-1-hydroxy-cis-11-octadecen-3-one + CO2
show the reaction diagram
palmitoyl-CoA + L-alanine
CoA + (2S)-2-aminooctadecan-3-one + CO2
show the reaction diagram
palmitoyl-CoA + L-serine
3-dehydrosphinganine + CoA + CO2
show the reaction diagram
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?
palmitoyl-CoA + L-serine
CoA + 3-dehydro-D-sphinganine + CO2
show the reaction diagram
S-(2-oxoheptadecyl)-CoA + L-serine
CoA + ?
show the reaction diagram
stearoyl-CoA + L-serine
(2S)-2-amino-1-hydroxyicosan-3-one + CoA + CO2
show the reaction diagram
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?
stearoyl-CoA + L-serine
CoA + (2S)-2-amino-1-hydroxyicosan-3-one + CO2
show the reaction diagram
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?
stearoyl-CoA + L-serine
CoA + 2-amino-1-hydroxyeicosan-3-one + CO2
show the reaction diagram
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51% activity compared to that with palmitoyl-CoA
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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
myristoyl-CoA + L-serine
CoA + 2-amino-1-hydroxy-cis-11-hexadecen-3-one + CO2
show the reaction diagram
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SPT is the first and rate-limiting enzyme of sphingolipid biosynthesis
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?
myristoyl-CoA + L-serine
CoA + ? + CO2
show the reaction diagram
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recombinant SPTLC3 subunit in HEK-293 cells
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?
palmitoyl-CoA + L-alanine
CoA + (2S)-2-aminooctadecan-3-one + CO2
show the reaction diagram
O15270
wild-type enzyme can metabolize L-alanine under certain conditions
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?
palmitoyl-CoA + L-serine
CoA + 3-dehydro-D-sphinganine + CO2
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
pyridoxal 5'-phosphate
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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NaCl, LiCl, MgCl2, MnCl2 have no effect on activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2S,3R)-2-amino-12-hydroxy-2-hydroxymethyl-3-sulfooxy-octadecanoic acid
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IC50: 5.4 nM
(2S,3R)-2-amino-12-[(Z)-hydroxyimino]-2-hydroxymethyl-3-sulfooxy-octadecanoic acid
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IC50: 30 nM
(2S,3R)-2-amino-3,12-dihydroxy-2-hydroxymethyl-octadecanoic acid
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IC50: 3.2 nM
(2S,3R)-2-amino-3-hydroxy-2-hydroxymethyl-12-oxo-octadecanoic acid
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IC50: 3.5 nM
(2S,3R)-2-amino-3-hydroxy-2-hydroxymethyl-12-oxo-octadecanoic acid methyl ester
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IC50: 17 nM
3-hydroxypropionate
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competitive to L-serine
4-amino-3-isoxazolidone
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D-cycloserine and L-cycloserine are inhibitors, L-cycloserine is 14-fold more effective than D-cycloserine
alpha-methyl-DL-serine
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competitive to L-serine
beta-chloro-L-alanine
beta-Haloalanines
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ceramide 1-phosphate
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from bovine brain, inhibits the enzyme and blocks apoptosis in alveolar macrophages, overview
cis-4-methylsphingosine
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time- and concentration-dependent, causes drastic morphological changes of the cells in vivo
cis-5-methylsphingosine
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weak inhibition
cis-sphingosine
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weak inhibition
cysteine
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competitive to L-serine
L-alanine
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inhibition of serine utilization
L-Cycloserine
lipoxamycin
mycotoxin fumonisin B1
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enzyme sensitivity to the inhibitor is increased by small subunit ssSPTa overexpression
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myriocin
myrocin
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O-phosphoserine
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competitive to L-serine
palmitoyl CoA
enzyme shows remarkable substrate inhibition at palmitoyl-CoA concentrations higher than 0.1 nM
palmitoyl-CoA
serine methylester
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competitive to L-serine
sphingofungin B
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sulfamisterin
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antibiotic derived from Pycnidiella sp., IC50: 3 nM
thermozymocidin
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i.e. ISP-1; strong inhibition, reversible by sphingosine
threonine
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competitive to L-serine
trans-4-methylsphingosine
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trans-5-methylsphingosine
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weak inhibition
additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
dithiothreitol
EDTA
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required for enzyme activity
etoposide
fenretinide
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up-regulates enzyme activity in neuroblastoma cells
pioglitazone
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increases the enzyme activity in vitro and in vivo independent of standard or high-fat diet
retinoic acid
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up-regulates enzyme activity in embryonic carcinoma cell ine PCC7-Mz1
S-(2-oxoheptadecyl)-CoA
binds to the smSPT-external aldimine complex and enhances the exchange rate of the alpha-proton of L-serine by smSPT
small activating subunit of serine palmitoyltransferase
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ssSPT, the small subunits of human serine palmitoyltransferase (hssSPTs) are glycoproteins and activate the catalytic hLCB1/hLCB2 heterodimer. Two isoforms exist, ssSPTa and ssSPTb, a single amino acid, residue 25, difference between ssSPTa and ssSPTb is responsible for the acyl-CoA preference of heterotrimers containing each isoform. the role of the small activating subunits of serine palmitoyltransferase, ssSPTs, is to increase SPT activity without compromising substrate specificity. Activity and acyl-CoA selectivity of the ssSPTs reside in the conserved core. Deletion of the N-terminal 10 amino acids of small activating subunit of serine palmitoyltransferase isoforms ssSPTa or ssSPTb has no effect on the ability of the proteins to activate hLCB1/hLCB2a heterodimers sufficiently to complement growth of yeast lacking endogenous serine palmitoyltransferase. The region responsible for the acyl-CoA selectivity of ssSPTa lays between residues Ser11 and Glu27, the acyl-CoA selectivity does not lie in the C-terminal region of ssSPTb, overview
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small subunits of serine palmitoyltransferase
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additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
9.6
L-alanine
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C133W mutant protein, pH not specified in the publication, temperature not specified in the publication
0.1 - 10.6
L-serine
0.03
myristoyl-CoA
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pH 8.0, 37C, recombinant SPTLC3
0.019 - 1.2
palmitoyl-CoA
0.0129
stearoyl-CoA
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pH not specified in the publication, temperature not specified in the publication
additional information
L-alanine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.005 - 1.54
L-serine
0.009 - 1.15
palmitoyl-CoA
0.083
stearoyl-CoA
Sphingomonas wittichii
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pH not specified in the publication, temperature not specified in the publication
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.002 - 3.437
L-serine
95
0.136 - 32.02
palmitoyl-CoA
128
6.416
stearoyl-CoA
Sphingomonas wittichii
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pH not specified in the publication, temperature not specified in the publication
526
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2 - 5
L-alanine
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0000054
(2S,3R)-2-amino-12-hydroxy-2-hydroxymethyl-3-sulfooxy-octadecanoic acid
Cricetulus griseus
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IC50: 5.4 nM
0.00003
(2S,3R)-2-amino-12-[(Z)-hydroxyimino]-2-hydroxymethyl-3-sulfooxy-octadecanoic acid
Cricetulus griseus
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IC50: 30 nM
0.0000032
(2S,3R)-2-amino-3,12-dihydroxy-2-hydroxymethyl-octadecanoic acid
Cricetulus griseus
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IC50: 3.2 nM
0.0000035
(2S,3R)-2-amino-3-hydroxy-2-hydroxymethyl-12-oxo-octadecanoic acid
Cricetulus griseus
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IC50: 3.5 nM
0.000017
(2S,3R)-2-amino-3-hydroxy-2-hydroxymethyl-12-oxo-octadecanoic acid methyl ester
Cricetulus griseus
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IC50: 17 nM
0.000003
sulfamisterin
Cricetulus griseus
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antibiotic derived from Pycnidiella sp., IC50: 3 nM
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.000018
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HEK cell extract
0.000044
0.0000465
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activity in microsomes
0.00011
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substrate alanine, C133W mutant protein, pH not specified in the publication, temperature not specified in the publication
0.00027
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0.000275
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substrate serine, C133W mutant protein, pH not specified in the publication, temperature not specified in the publication
0.00135
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substrate serine, wild type protein, pH not specified in the publication, temperature not specified in the publication
0.057 - 0.084
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0.7
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purified enzyme
additional information
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.7 - 8.6
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about 50% of activity maximum at pH 6.7 and pH 8.6
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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embryonic cell line PCC7-Mz1
Manually annotated by BRENDA team
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the cell shows very low enzyme activity due to deficiency of subunit LCB1
Manually annotated by BRENDA team
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strong overexpression of both SPT subunits
Manually annotated by BRENDA team
vascular; vascular
Manually annotated by BRENDA team
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protein expression of SPT in both psoriatic epidermis and non-lesional epidermis is investigated. Expression of SPT in psoriatic epidermis is significantly less than that of the non-lesional epidermis, which is inversely correlated with PASI score
Manually annotated by BRENDA team
except for ovarian epithelium; except for ovarian epithelium
Manually annotated by BRENDA team
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age-dependent amount of enzyme activity
Manually annotated by BRENDA team
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isozyme SPT2
Manually annotated by BRENDA team
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strong overexpression of both SPT subunits
Manually annotated by BRENDA team
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strong overexpression of both SPT subunits
Manually annotated by BRENDA team
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beta-cells
Manually annotated by BRENDA team
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strong overexpression of both SPT subunits
Manually annotated by BRENDA team
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small subunit ssSPTa transcripts are more enriched in all organs and over 400fold more abundant in pollen than small subunit ssSPTb transcripts
Manually annotated by BRENDA team
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strong overexpression of both SPT subunits
Manually annotated by BRENDA team
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strong overexpression of both SPT subunits
Manually annotated by BRENDA team
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high SPTLC3 content
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information