Information on EC 2.3.1.76 - retinol O-fatty-acyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.3.1.76
-
RECOMMENDED NAME
GeneOntology No.
retinol O-fatty-acyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
acyl-CoA + retinol = CoA + retinyl ester
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Retinol metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
acyl-CoA:retinol O-acyltransferase
Acts on palmitoyl-CoA and other long-chain fatty-acyl derivatives of CoA.
CAS REGISTRY NUMBER
COMMENTARY hide
81295-48-9
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
cat
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
fish, brook trout
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
-
neutral lipid synthesis enzyme acyl-CoA:diacylglycerol acyltransferase DGAT1 functions as the major acyl-CoA:retinol acyltransferase. When dietary retinol is abundant, DGAT1 deficiency results in elevated levels of retinoic acid in skin and cyclical hair loss, both are prevented by dietary retinol deprivation. DGAT1-deficient skin exhibits enhanced sensitivity to topically administered retinol. Deletion of the enzyme specifically in the epidermis causes alopecia
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 + retinol
CoA + retinyl ester
show the reaction diagram
all-trans retinol + palmitoyl-CoA
all-trans-retinyl palmitate + CoA
show the reaction diagram
lauroyl-CoA + retinol
CoA + retinyllaurate
show the reaction diagram
octanoyl-CoA + retinol
CoA + retinyloctanoate
show the reaction diagram
oleoyl-CoA + retinol
CoA + retinyloleolate
show the reaction diagram
palmitoyl-CoA + 11-cis-retinol
CoA + 11-cis-retinyl palmitate
show the reaction diagram
palmitoyl-CoA + 11-cis-retinol
CoA + 11-cis-retinylpalmitate
show the reaction diagram
-
-
-
-
?
palmitoyl-CoA + all-trans-retinol
CoA + all-trans-retinyl palmitate
show the reaction diagram
palmitoyl-CoA + all-trans-retinol
CoA + all-trans-retinylpalmitate
show the reaction diagram
-
-
-
-
?
palmitoyl-CoA + retinol
CoA + retinyl palmitate
show the reaction diagram
palmitoyl-CoA + retinol
CoA + retinylpalmitate
show the reaction diagram
stearoyl-CoA + retinol
CoA + retinylstearate
show the reaction diagram
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
acyl-CoA + retinol
CoA + retinyl ester
show the reaction diagram
all-trans retinol + palmitoyl-CoA
all-trans-retinyl palmitate + CoA
show the reaction diagram
-
-
-
-
?
palmitoyl-CoA + 11-cis-retinol
CoA + 11-cis-retinyl palmitate
show the reaction diagram
palmitoyl-CoA + all-trans-retinol
CoA + all-trans-retinyl palmitate
show the reaction diagram
palmitoyl-CoA + retinol
CoA + retinyl palmitate
show the reaction diagram
-
-
-
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
-
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(6R)-6beta-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide phosphate
-
activity inhibited at 0.5%
2,3,7,8-tetrachlorodibenzo-p-dioxin
-
decreased activity
5,5'-dithiobis(2-nitrobenzoic acid)
-
activity inhibited above 2 mM
all-trans-retinylbromoacetate
-
-
cellular retinol-binding protein
-
specific inhibition of retinol fatty-acyltransferase by capturing substrate
-
p-chloromercuribenzoate
-
activity abolished at 5 mM
p-Chloromercuriphenylsulfonic acid
-
activity abolished at 6 mM
p-hydroxymercuribenzoate
-
activity inhibited at 2 and 6 mM
progesterone
Sodium deoxycholate
-
activity inhibited at 0.5%
sodium taurocholate
-
activity abolished at 8 mM
XP620
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
bovine serum albumin
-
dithiothreitol
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0087
11-cis-retinol
-
; pH 7.5, 37°C, retinal pigment epithelium microsomes
0.0041 - 0.0048
all-trans-retinol
0.0139
palmitoyl-CoA
0.016 - 0.0259
retinol
additional information
additional information
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000045 - 0.00045
XP620
additional information
additional information
-
inhibition kinetics depend highly on retinol concentration, overview, recombinant enzyme
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0000887 - 0.00011
XP620
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.000023
-
11-cis-retinyl ester synthesis in absence of cellular retinol-binding protein
0.00045
-
ARAT activity of recombinant acyl coenzyme A:diacylglycerol acyltransferase isozyme 2 in SF9 cell membrane preparation
0.00084
-
ARAT activity of recombinant acyl coenzyme A:monoacylglycerol acyltransferase isozyme 3 in SF9 cell membrane preparation
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 8
-
maximum esterification
7.4
-
assay at
7.5 - 8
-
assay at
7.8
-
maximal activity
8
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3 - 11
-
decreasing activity below pH 5
6 - 10
-
maximum esterification between pH 7-8
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22
-
asay at room temperature
25
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
squamous SCC12b and SCC13b lines are common type of skin cancer that has reduced capacity to esterify retinol relative to normal keratinocytes
Manually annotated by BRENDA team
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-
Manually annotated by BRENDA team
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D033 line
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
primary cell culture
Manually annotated by BRENDA team
-
very low expression level
Manually annotated by BRENDA team
additional information
-
cells and tissues from DGAT1-deficient mice exhibit reduced ARAT activity; DGAT1 exhibits ARAT activity in in vitro assays and accounts for a large portion of ARAT activity in the liver, testis, and kidney of mice
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 11
-
activity is decreased below
487497
7.2
-
phosphate buffer
487494
7.8
-
Tris-HCl buffer
487497
8
-
Tris acetate
487491
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
70
-
activity abolished in 20 min
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70ºC, phosphate buffer, pH 7.2, DTT, 12 months
-
-70ºC, phosphate buffer, pH 7.4, DTT, 2 months
-
-80ºC, Tris-acetate, pH 7, DTT, 6 months
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme partially by membrane preparation
-
partial purification by differential centrifugation
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
chromosomal location, expression of the FLAG-tagged enzyme in Spodoptera frugiperda Sf9 cells and in COS-7 cells; expression in insect cells or in COS-7 cells
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expression in HEK-293T cells
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expression in Spodoptera frugiperda Sf9 cell membranes using the baculovrisu transfection system
-
expression in Spodoptera frugiperda Sf9 cells
-
FLAG-tagged enzyme expression in COS-7 cells, the cells expressing DGAT1 show ARAT and WAX synthase, EC 2.3.1.75, activities
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
cells and tissues from DGAT1-deficient mice exhibit reduced ARAT activity, and the mice have increased levels of unesterified retinol in their livers on a high-retinol diet; DGAT1 deficiency also perturbs retinol metabolism in the livers of Dgat-/- mice, hepatic levels of unesterified retinol are increased in Dgat-/- mice challenged with high-retinol diets
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine