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Information on EC 2.5.1.26 - alkylglycerone-phosphate synthase and Organism(s) Mus musculus and UniProt Accession Q8C0I1
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2.5.1.26 alkylglycerone-phosphate synthaseIUBMB Comments
The ester-linked fatty acid of the substrate is cleaved and replaced by a long-chain alcohol in an ether linkage.
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Word Map
- 2.5.1.26
- ether
- shikimate
- dah7ps
- chorismate
- plasmalogens
-
chondrodysplasia
-
rhizomelic
- punctata
- zellweger
- prephenate
-
phenylalanine-sensitive
- dhap-at
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4.1.2.15
-
tyrosine-sensitive
-
8-phosphate
- hexadecanol
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5-enolpyruvylshikimate
- d-erythrose
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tryptophan-sensitive
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plasmalogen-deficient
- medicine
-
dihydroxyacetone-phosphate
- pharmacology
The taxonomic range for the selected organisms is: Mus musculus
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Reaction Schemes
Synonyms
3-deoxy-d-arabino-heptulosonate 7-phosphate synthase, alkyl-dhap, alkyl-dihydroxyacetonephosphate synthase, alkylglycerone phosphate synthase, alkyldihydroxyacetonephosphate synthase, alkyl dihydroxyacetone phosphate synthase, alkylglyceronephosphate synthase, alkyldihydroxyacetone phosphate synthase, alkylglycerone-phosphate synthase, alkyl-dihydroxyacetonephosphate-synthase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
alkyl DHAP synthetase
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alkyl dihydroxyacetone phosphate synthase
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alkyl dihydroxyacetone phosphate synthetase
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alkyl-DHAP
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alkyldihydroxyacetone phosphate synthase
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alkyldihydroxyacetonephosphate synthase
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alkyldihydroxyacetonephosphate synthetase
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alkylglycerone phosphate synthase
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synthase, alkylglycerone phosphate
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synthetase, alkyldihydroxyacetone phosphate
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
mechanism
-
1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
ping-pong mechanism
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1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
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
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ether formation
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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
102484-74-2
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64060-42-0
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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
1-acyl-glycerone 3-phosphate + a long-chain alcohol
an alkyl-glycerone 3-phosphate + a long-chain acid anion
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-
-
-
?
1-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
palmitoyldihydroxyacetone phosphate + hexadecanol
1-O-hexadecyldihydroxyacetone phosphate + palmitate
1-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
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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
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?
1-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
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forms the ether bond found in alkyl and alk-1-enyl glycerolipids
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-
?
1-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
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first committed step in biosynthesis of ether-linked glycerolipids
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-
?
palmitoyldihydroxyacetone phosphate + hexadecanol
1-O-hexadecyldihydroxyacetone phosphate + palmitate
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-
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?
palmitoyldihydroxyacetone phosphate + hexadecanol
1-O-hexadecyldihydroxyacetone phosphate + palmitate
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-
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?
additional information
additional information
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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
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-
?
additional information
additional information
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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
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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
1-acyl-glycerone 3-phosphate + a long-chain alcohol
an alkyl-glycerone 3-phosphate + a long-chain acid anion
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-
-
-
?
1-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
1-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
-
forms the ether bond found in alkyl and alk-1-enyl glycerolipids
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-
?
1-acylglycerone 3-phosphate + long-chain alcohol
alkylglycerone 3-phosphate + long-chain acid anion + H+
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first committed step in biosynthesis of ether-linked glycerolipids
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-
?
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
cataracts and male infertility in blind sterile 2 (bs2) mice are caused by a spontaneous hypomorphic mutation in gene agp. Infertility in bs2 mice is due to the aberrant formation of multicellular cellular clusters that undergo apoptosis. The majority of Agps knock-out mice die embryonically. Correlations of RCDP3 and bs2 phenotypes, detailed overview
malfunction
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AGPS protein level and phosphatidylethanolamine plasmalogen level are decreased in amyloid-beta protein precursor-deficient cells and brains, overview
metabolism
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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
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). ADAS_MOUSE
645
0
71684
Swiss-Prot
other Location (Reliability: 2)
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
generation of gene Agps knockout mice, phenotype, overview
additional information
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generation of gene Agps knockout mice, phenotype, overview
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
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, 20% ethylene glycol, solubilized and delipidated enzyme is stable for 1 month
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene Agps, semiquantitative RT-PCR expression analysis of wild-type and mutant enzymes
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Brown, A.J.; Snyder, F.
Alkyldihydroxyacetone-P synthase. Solubilization, partial purification, new assay method, and evidence for a ping-pong mechanism
J. Biol. Chem.
257
8835-8839
1982
Mus musculus
Brown, A.; Snyder, F.
Alkyldihydroxyacetonephosphate synthase
Methods Enzymol.
209
377-384
1992
Mus musculus
Brown, A.J.; Snyder, F.
The mechanism of alkyldihydroxyacetone-P synthase. Formation of [3H]H2O from acyl[1-R-3H]dihydroxyacetone-P by purified alkyldihydroxyacetone-P synthase in the absence of acylhydrolase activity
J. Biol. Chem.
258
4184-4189
1983
Mus musculus
Van den Bosch, H.; de Vet, E.C.J.M.
Alkyl-dihydroxyacetonephosphate synthase
Biochim. Biophys. Acta
1348
35-44
1997
Cavia porcellus, Homo sapiens, Mus musculus
Grimm, M.O.; Kuchenbecker, J.; Rothhaar, T.L.; Groesgen, S.; Hundsdoerfer, B.; Burg, V.K.; Friess, P.; Mueller, U.; Grimm, H.S.; Riemenschneider, M.; Hartmann, T.
Plasmalogen synthesis is regulated via alkyl-dihydroxyacetonephosphate-synthase by amyloid precursor protein processing and is affected in Alzheimers disease
J. Neurochem.
116
916-925
2011
Homo sapiens, Mus musculus
Liegel, R.P.; Ronchetti, A.; Sidjanin, D.J.
Alkylglycerone phosphate synthase (AGPS) deficient mice: models for rhizomelic chondrodysplasia punctate type 3 (RCDP3) malformation syndrome
Mol. Genet. Metab. Rep.
1
299-311
2014
Homo sapiens (O00116), Homo sapiens, Mus musculus (Q8C0I1), Mus musculus, Mus musculus C57/BL6J (Q8C0I1)
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