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
2.5.1.26
-
RECOMMENDED NAME
GeneOntology No.
alkylglycerone-phosphate synthase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
show the reaction diagram
enzyme also catalyzes the following reactions: 1. acyl exchange reaction in which palmitic acid is incorporated into palmitoyldihydroxyacetone phosphate, 2. alkyl exchange reaction in which hexadecanol is incorporated into hexadecyldihydroxyacetone phosphate; ping-pong mechanism
-
1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
show the reaction diagram
mechanism
-
1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
show the reaction diagram
ping-pong mechanism
-
1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
show the reaction diagram
ping-pong mechanism
-
1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
show the reaction diagram
mechanism
-
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 ACCESSION NO.
COMMENTARY
LITERATURE
ether formation
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
Ether lipid metabolism
-
Metabolic pathways
-
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.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
3-deoxy-D-arabino-heptulosonate 7-phosphate synthase
Vitis vinifera x Vitis riparia, Vitis vinifera x Vitis vinifera
-
-
alkyl DHAP synthetase
-
-
-
-
alkyl dihydroxyacetone phosphate synthase
-
-
-
-
alkyl dihydroxyacetone phosphate synthetase
-
-
-
-
alkyl-DHAP
-
-
-
-
alkyl-dihydroxyacetonephosphate synthase
-
-
alkyl-dihydroxyacetonephosphate-synthase
-
-
alkyldihydroxyacetone phosphate synthase
-
-
-
-
alkyldihydroxyacetonephosphate synthase
-
-
-
-
alkyldihydroxyacetonephosphate synthetase
-
-
-
-
alkylglycerone phosphate synthase
-
-
-
-
DHAP-S
Vitis vinifera x Vitis riparia, Vitis vinifera x Vitis vinifera
-
-
synthase, alkylglycerone phosphate
-
-
-
-
synthetase, alkyldihydroxyacetone phosphate
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
102484-74-2
-
64060-42-0
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
recombinant enzyme
-
-
Manually annotated by BRENDA team
chimpanzee
-
-
Manually annotated by BRENDA team
induction by lipopolysaccaride
-
-
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 ACCESSION NO.
COMMENTARY
LITERATURE
malfunction
-
in plasmalogen-deficient Chinese hamster ovary mutant, ZPEG251, alkyl-dihydroxyacetonephosphate synthase, is defective. ADAPS mRNA is barely detectable by Northern blot and RT-PCR analyses. Defect of ADAPS expression is also assessed by immunoblot. Ectopic expression of ADAPS-EGFP, enhances the plasmalogen level
malfunction
-
AGPS protein level and phosphatidylethanolamine plasmalogen level are decreased in amyloid-beta protein precursor-deficient cells and brains, overview
metabolism
-
alkyl-dihydroxyacetonephosphate-synthase, AGPS, is a rate limiting enzyme in plasmalogen synthesis, catalyzing the initial committed step in plasmalogen synthesis, phosphatidylethanolamine plasmalogen de novo synthesis, overview. Plasmalogens are major brain lipids
physiological function
Vitis vinifera x Vitis riparia, Vitis vinifera x Vitis vinifera
-
involved in aromatic amino acid metabolism
physiological function
-
plasmalogens are decreased as a consequence of Alzheimer's disease and regulated by amyloid-beta precursor protein processing under physiological conditions. Under the pathological situation of Alzheimer's disease, increased amyloid-beta levels lead to increased reactive oxidative species production, reduced AGPS protein and plasmalogen level, overview. Alterations in amyloid precursor protein-dependent changes of AGPS expression result in reduced protein and plasmalogen levels
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
show the reaction diagram
-
1-acylglycerone 3-phosphate is acyldihydroxyacetone phosphate, the ester-linked fatty acid of the substrate is cleaved and replaced by a long-chain alcohol in the ether
-
?
1-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
show the reaction diagram
-
forms the ether bond found in alkyl and alk-1-enyl glycerolipids
-
-
-
1-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
show the reaction diagram
-
first committed step in biosynthesis of ether-linked glycerolipids
-
-
-
1-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
show the reaction diagram
-
2 separate alkylglycerone-phosphate synthases, one in microsomes and another in peroxisomes might be engaged in biosynthesis of 1-O-alkylglycerolipids in rat liver
-
-
-
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 + hexadecanol
1-O-hexadecyldihydroxyacetone phosphate + palmitate
show the reaction diagram
-
-
-
ir
palmitoyldihydroxyacetone phosphate + hexadecanol
1-O-hexadecyldihydroxyacetone phosphate + palmitate
show the reaction diagram
-
-
-
-
?
palmitoyldihydroxyacetone phosphate + hexadecanol
1-O-hexadecyldihydroxyacetone phosphate + palmitate
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
-
-
-
-
?
palmitoyldihydroxyacetone phosphate + octadecanol
palmitate + 1-O-octadecyldihydroxyacetone phosphate
show the reaction diagram
-
-
-
-
?
palmitoyldihydroxyacetone phosphate + octadecanol
palmitate + 1-O-octadecyldihydroxyacetone phosphate
show the reaction diagram
-
-
-
-
?
palmitoyldihydroxyacetone phosphate + octadecanol
palmitate + 1-O-octadecyldihydroxyacetone phosphate
show the reaction diagram
O97157, -
-
-
-
?
stearoyldihydroxyacetone phosphate + hexadecanol
stearate + 1-O-hexadecyldihydroxyacetone phosphate
show the reaction diagram
-
-
-
-
?
stearoyldihydroxyacetone phosphate + hexadecanol
stearate + 1-O-hexadecyldihydroxyacetone phosphate
show the reaction diagram
O97157, -
-
-
-
?
stearoyldihydroxyacetone phosphate + octadecanol
stearate + 1-O-octadecyldihydroxyacetone phosphate
show the reaction diagram
-
-
-
-
?
1-O-hexadecyldihydroxyacetone phosphate + hexadecanol
long-chain acid anion + 1-O-hexadecyldihydroxyacetone phosphate
show the reaction diagram
-
-
-
-
?
additional information
additional information
-
-
-
-
-
-
additional information
additional information
-
-
-
two reaction products: alkylglycerone phosphate and alkylglycerone, alkylglycerone phosphate is mainly synthesized by the peroxisomal synthase, whereas the inverse proportion is observed with the microsomal enzyme
-
additional information
additional information
-
-
overview on substrate specificity
-
-
-
additional information
additional information
-
-
specific for acyldihydroxyacetone phosphate, acyldihydroxyacetone or 1-acyl-sn-glycerol 3-phosphate cannot substitute for acyldihydroxyacetone phosphate, the acyl group chain length in acyldihydroxyacetone phosphate should be C12 or longer
-
-
-
additional information
additional information
-
-
alkyldihydroxyacetone phosphate synthase also catalyzes the following reactions: 1. acyl exchange reaction in which palmitic acid is incorporated into palmitoyldihydroxyacetone phosphate, 2. alkyl exchange reaction in which hexadecanol is incorporated into hexadecyldihydroxyacetone phosphate
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
-
forms the ether bond found in alkyl and alk-1-enyl glycerolipids
-
-
-
1-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
show the reaction diagram
-
first committed step in biosynthesis of ether-linked glycerolipids
-
-
-
1-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
show the reaction diagram
-
2 separate alkylglycerone-phosphate synthases, one in microsomes and another in peroxisomes might be engaged in biosynthesis of 1-O-alkylglycerolipids in rat liver
-
-
-
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
FAD
-
involved in initial oxidation of substrate
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
2,4-Dinitrofluorobenzene
-
1 mM, 2% activity
3-Bromo-2-oxoheptadecyl phosphate
-
-
acyldihydroxyacetone phosphate
-
high concentration, substrate inhibition
fatty acids
-
competitive to fatty alcohols
fatty acids
-
-
hexadecanol
O97157, -
inhibitory above 0.3 mM
Mg2+
-
5 mM, 70% activity
N-ethylmaleimide
-
5 mM, 15% activity
NaCl
O97157, -
50% inhibition at 0.6 M
p-Bromophenacylbromide
-
1 mM, 55% activity
palmitoyl-dihydroxyacetonphosphate
O97157, -
inhibitory above 0.1 mM
-
Phenylglyoxal
-
inactivation
Zn2+
-
5 mM, 8% activity
Mn2+
-
5 mM, 6% activity
additional information
-
not inhibitory: Ca2+
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.04
-
hexadecanol
-
cosubstrate palmitoyldihydroxyacetone phosphate
0.042
-
hexadecanol
O97157, -
-
0.044
-
hexadecanol
-
-
0.072
-
hexadecanol
-
cosubstrate palmitoyldihydroxyacetone phosphate
0.1
-
hexadecanol
-
cosubstrate hexadecyldihydroxyacetone phosphate
0.115
-
Hexadecyldihydroxyacetone phosphate
-
cosubstrate hexadecanol, 0.4 mM
0.192
-
Hexadecyldihydroxyacetone phosphate
-
cosubstrate hexadecanol, 0.05 mM
0.038
-
octadecanol
-
-
0.045
-
Palmitoyldihydroxyacetone phosphate
-
cosubstrate hexadecanol
0.068
-
Palmitoyldihydroxyacetone phosphate
-
cosubstrate hexadecanol
0.1
-
Palmitoyldihydroxyacetone phosphate
O97157, -
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
0.00714
-
-
-
0.0208
-
-
-
0.067
-
-
-
0.35
-
-
-
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
8
-
-
assay at
8
-
-
assay at
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.5
9
-
pH 6.5: about 50% of maximum activity, pH 9.0: about 30% of maximum activity
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
37
-
-
assay at
37
-
-
assay at
37
-
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
-
low activity
Manually annotated by BRENDA team
additional information
-
enzyme is present in all tissues examined, overview
Manually annotated by BRENDA team
additional information
-
enzyme is present in all tissues examined
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
at least the active site of the integral membrane protein is localized exclusively at the inner surface of the peroxisomal membrane
Manually annotated by BRENDA team
-
entire enzyme is located inside peroxisomes
Manually annotated by BRENDA team
O97157, -
type-1 peroxisomal targeting signal
Manually annotated by BRENDA team
-
type-1 peroxisomal targeting signal
Manually annotated by BRENDA team
-
type-2 peroxisomal targeting signal
Manually annotated by BRENDA team
-
enzyme is not an integral membrane protein
Manually annotated by BRENDA team
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
65000
-
-
gel filtration, phosphocellulose chromatography
79000
-
-
radiation inactivation
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
O97157, -
x * 68900, deduced from gene sequence
?
-
x * 65000, SDS-PAGE
?
-
x * 70585, calculated
monomer
-
1 * 65000, SDS-PAGE
additional information
-
enzyme interacts with dihydroxyacetone phosphate acyltransferase in a heterotrimeric complex
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
sequence contains neither transmembrane helices nor secretory signal sequences, but FAD/FMN-binding domains
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
loss of activity on freezing and thawing
-
sensitive to sulfhydryl reagents, dithiothreitol prevents oxidation
-
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
4°C, 50% loss of activity after 10 days
-
4°C, 20% ethylene glycol, solubilized and delipidated enzyme is stable for 1 month
-
in liquid N2, stable for 1 year
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
overview
-
partial
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
overview
-
AGPS expression anaysis by quantitative RT-PCR analysis
-
overview
-
AGPS expression anaysis by quantitative RT-PCR analysis
-
overview
-
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
the amyloid precursor protein intracellular domain increases the expression of the alkyl-dihydroxyacetonephosphate-synthase in vivo and in vitro
-
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
C576A
-
187% of wild type activity
R419K
-
1% of wild type activity
S367A
-
4% of wild type activity
H617A
-
complete loss of activity
additional information
-
deletion of C-terminal 5 amino acids, inactive enzyme
R419H
-
inactive enzyme
additional information
-
generation of homo- and heterozygous APP knock-out mice, APP-/-, APP+/-, and mice expressing a truncated amyloid precursor protein, APP, the construct lacks the last 15 amino acids, APPDELTA/DELTA, that includes the presumably critical YENPTY motif, where adaptor proteins like Fe65 and X11 are proposed to bind through their phosphotyrosine-binding domains and which are responsible for nuclear targeting of APP intracellular domain
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
medicine
-
in fibroblast cell lines derived from Zellweger syndrome and rhizomelic chondrodysplasia punctata patients enzyme is mainly present as precursor form
medicine
-
enzyme levels are strongly reduced in fibroblasts derived from Zellweger syndrome and rhizomelic chondrodysplasia punctata patients