Information on EC 2.5.1.26 - alkylglycerone-phosphate synthase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY hide
2.5.1.26
-
RECOMMENDED NAME
GeneOntology No.
alkylglycerone-phosphate synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ether formation
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Ether lipid metabolism
-
-
Metabolic pathways
-
-
plasmalogen biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
1-acyl-glycerone-3-phosphate:long-chain-alcohol O-3-phospho-2-oxopropanyltransferase
The ester-linked fatty acid of the substrate is cleaved and replaced by a long-chain alcohol in an ether linkage.
CAS REGISTRY NUMBER
COMMENTARY hide
102484-74-2
-
64060-42-0
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
chimpanzee
-
-
Manually annotated by BRENDA team
induction by lipopolysaccaride
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
Vitis vinifera x Vitis riparia
-
-
-
Manually annotated by BRENDA team
Vitis vinifera x Vitis vinifera
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
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
1-acyl-glycerone 3-phosphate + a long-chain alcohol
an alkyl-glycerone 3-phosphate + a long-chain acid anion
show the reaction diagram
1-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
show the reaction diagram
1-O-hexadecyldihydroxyacetone phosphate + hexadecanol
long-chain acid anion + 1-O-hexadecyldihydroxyacetone phosphate
show the reaction diagram
-
-
-
-
?
oleoyldihydroxyacetone phosphate + hexadecanol
oleate + 1-O-hexadecyldihydroxyacetone phosphate
show the reaction diagram
-
-
-
-
?
palmitoyldihydroxyacetone phosphate + hexadecanol
1-O-hexadecyldihydroxyacetone phosphate + palmitate
show the reaction diagram
palmitoyldihydroxyacetone phosphate + octadecanol
palmitate + 1-O-octadecyldihydroxyacetone phosphate
show the reaction diagram
stearoyldihydroxyacetone phosphate + hexadecanol
stearate + 1-O-hexadecyldihydroxyacetone phosphate
show the reaction diagram
stearoyldihydroxyacetone phosphate + octadecanol
stearate + 1-O-octadecyldihydroxyacetone phosphate
show the reaction diagram
-
-
-
-
?
additional information
additional information
-
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
1-acyl-glycerone 3-phosphate + a long-chain alcohol
an alkyl-glycerone 3-phosphate + a long-chain acid anion
show the reaction diagram
1-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FAD
-
involved in initial oxidation of substrate
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2,4-Dinitrofluorobenzene
-
1 mM, 2% activity
3-Bromo-2-oxoheptadecyl phosphate
-
-
acyldihydroxyacetone phosphate
-
high concentration, substrate inhibition
fatty acids
hexadecanol
inhibitory above 0.3 mM
Mg2+
-
5 mM, 70% activity
Mn2+
-
5 mM, 6% activity
N-ethylmaleimide
-
5 mM, 15% activity
NaCl
50% inhibition at 0.6 M
p-bromophenacylbromide
-
1 mM, 55% activity
palmitoyl-dihydroxyacetonphosphate
inhibitory above 0.1 mM
-
Phenylglyoxal
-
inactivation
Zn2+
-
5 mM, 8% activity
additional information
-
not inhibitory: Ca2+
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.04 - 0.1
hexadecanol
0.115 - 0.192
Hexadecyldihydroxyacetone phosphate
0.038
octadecanol
-
-
0.045 - 0.1
Palmitoyldihydroxyacetone phosphate
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00714
-
-
0.0208
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 9
-
pH 6.5: about 50% of maximum activity, pH 9.0: about 30% of maximum activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
-
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
65000
-
gel filtration, phosphocellulose chromatography
79000
-
radiation inactivation
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
-
1 * 65000, SDS-PAGE
additional information
-
enzyme interacts with dihydroxyacetone phosphate acyltransferase in a heterotrimeric complex
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
sequence contains neither transmembrane helices nor secretory signal sequences, but FAD/FMN-binding domains
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
loss of activity on freezing and thawing
-
sensitive to sulfhydryl reagents, dithiothreitol prevents oxidation
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, 20% ethylene glycol, solubilized and delipidated enzyme is stable for 1 month
-
4°C, 50% loss of activity after 10 days
-
in liquid N2, stable for 1 year
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
overview
partial
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
AGPS expression anaysis by quantitative RT-PCR analysis
overview
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the amyloid precursor protein intracellular domain increases the expression of the alkyl-dihydroxyacetonephosphate-synthase in vivo and in vitro
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C576A
-
187% of wild type activity
H617A
-
complete loss of activity
R419K
-
1% of wild type activity
S367A
-
4% of wild type activity
R419H
-
inactive enzyme
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
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