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Information on EC 2.3.1.76 - retinol O-fatty-acyltransferase
for references in articles please use BRENDA:EC2.3.1.76
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EC Tree 2 Transferases
2.3 Acyltransferases
2.3.1 Transferring groups other than aminoacyl groups
2.3.1.76 retinol O-fatty-acyltransferase
IUBMB Comments
Acts on palmitoyl-CoA and other long-chain fatty-acyl derivatives of CoA.
The enzyme appears in viruses and cellular organisms
- 2.3.1.76
- esterification
-
esterify
-
retinoids
- medicine
-
lecithin:retinol
- palmitate
- palmitoyl-coa
- diacylglycerols
-
unesterified
-
3hretinol
- hairless
-
palmitoyl
-
alumina
- chylomicron
- all-trans-retinaldehyde
-
dgats
- stearate
-
11-cis-retinaldehyde
-
11-cis-retinyl
-
photobleached
-
mid-gestation
-
all-trans-retinyl
showSynonyms
acyl coa:retinol acyltransferase, retinyl-ester synthase, acyl coenzyme a:retinol acyltransferase, 11-cis-arat, retinol fatty-acyltransferase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
acyl CoA:retinol acyltransferase
ArAT
retinol fatty-acyltransferase
-
-
-
-
additional information
additional information
-
the enzyme belongs to the acyl-CoA:diacylglycerol acyltransferase 2/acyl-CoA:monoacylglycerol acyltransferase, MGAT, gene family
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
acyl-CoA + retinol = CoA + retinyl ester
-
-
-
-
acyl-CoA + retinol = CoA + retinyl ester
enzyme mechanism and role in the visual cycle
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Acyl group transfer
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
KEGG
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SYSTEMATIC NAME
IUBMB Comments
acyl-CoA:retinol O-acyltransferase
Acts on palmitoyl-CoA and other long-chain fatty-acyl derivatives of CoA.
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CAS REGISTRY NUMBER
COMMENTARY
81295-48-9
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
palmitoyl-CoA + 11-cis-retinol
CoA + 11-cis-retinylpalmitate
-
Substrates: -
Products: -
Products: -
?
palmitoyl-CoA + all-trans-retinol
CoA + all-trans-retinylpalmitate
-
Substrates: -
Products: -
Products: -
?
acyl-CoA + retinol
CoA + retinyl ester
-
Substrates: -
Products: -
Products: -
?
acyl-CoA + retinol
CoA + retinyl ester
-
Substrates: -
Products: -
Products: -
?
all-trans retinol + palmitoyl-CoA
all-trans-retinyl palmitate + CoA
-
Substrates: -
Products: -
Products: -
?
all-trans retinol + palmitoyl-CoA
all-trans-retinyl palmitate + CoA
-
Substrates: -
Products: -
Products: -
?
lauroyl-CoA + retinol
CoA + retinyllaurate
-
Substrates: -
Products: -
Products: -
?
octanoyl-CoA + retinol
CoA + retinyloctanoate
-
Substrates: -
Products: -
Products: -
?
octanoyl-CoA + retinol
CoA + retinyloctanoate
-
Substrates: -
Products: -
Products: -
?
oleoyl-CoA + retinol
CoA + retinyloleolate
-
Substrates: -
Products: -
Products: -
?
oleoyl-CoA + retinol
CoA + retinyloleolate
-
Substrates: -
Products: -
Products: -
?
palmitoyl-CoA + 11-cis-retinol
CoA + 11-cis-retinyl palmitate
-
Substrates: -
Products: -
Products: -
r
palmitoyl-CoA + 11-cis-retinol
CoA + 11-cis-retinyl palmitate
-
Substrates: esterification of 11-cis-retinol is four times greater than esterification of all-trans-retinol in Muller cells
Products: -
Products: -
?
palmitoyl-CoA + 11-cis-retinol
CoA + 11-cis-retinyl palmitate
-
Substrates: -
Products: -
Products: -
?
palmitoyl-CoA + all-trans-retinol
CoA + all-trans-retinyl palmitate
-
Substrates: -
Products: -
Products: -
r
palmitoyl-CoA + all-trans-retinol
CoA + all-trans-retinyl palmitate
-
Substrates: esterification of 11-cis-retinol is four times greater than esterification of all-trans-retinol in Muller cells
Products: -
Products: -
?
palmitoyl-CoA + all-trans-retinol
CoA + all-trans-retinyl palmitate
-
Substrates: -
Products: -
Products: -
?
palmitoyl-CoA + retinol
CoA + retinyl palmitate
-
Substrates: -
Products: -
Products: -
?
palmitoyl-CoA + retinol
CoA + retinylpalmitate
-
Substrates: -
Products: -
Products: -
?
palmitoyl-CoA + retinol
CoA + retinylpalmitate
-
Substrates: -
Products: -
Products: -
?
palmitoyl-CoA + retinol
CoA + retinylpalmitate
-
Substrates: -
Products: -
Products: -
?
palmitoyl-CoA + retinol
CoA + retinylpalmitate
-
Substrates: polyunsaturated derivatives are poor substrates
Products: -
Products: -
?
palmitoyl-CoA + retinol
CoA + retinylpalmitate
-
Substrates: predominant fatty acid among tissue retinyl esters
Products: -
Products: -
?
palmitoyl-CoA + retinol
CoA + retinylpalmitate
-
Substrates: better effect with long chain fatty acids
Products: -
Products: -
?
palmitoyl-CoA + retinol
CoA + retinylpalmitate
-
Substrates: better effect with long chain fatty acids
Products: -
Products: -
?
palmitoyl-CoA + retinol
CoA + retinylpalmitate
-
Substrates: -
Products: -
Products: -
?
palmitoyl-CoA + retinol
CoA + retinylpalmitate
-
Substrates: -
Products: -
Products: -
?
stearoyl-CoA + retinol
CoA + retinylstearate
-
Substrates: -
Products: -
Products: -
?
stearoyl-CoA + retinol
CoA + retinylstearate
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: ARAT may complement LRAT, EC 2.3.1.135, to provide additional retinyl-ester synthase activity under conditions of high all-trans-retinol
Products: -
Products: -
?
additional information
?
-
-
Substrates: the multifunctional O-acyltransferase likely plays an important role in lipid metabolism in human skin
Products: -
Products: -
?
additional information
?
-
-
Substrates: the multifunctional enzyme plays an important role in lipid metabolism in human skin
Products: -
Products: -
?
additional information
?
-
-
Substrates: acyl coenzyme A:diacylglycerol acyltransferase, DGAT, EC 2.3.1.20, and acyl coenzyme A:monoacylglycerolol acyltransferase, MGAT, EC 2.3.1.22, also show activity with retinol, overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: the reaction is also catalyzed by the acyl coenzyme A:diacylglycerol acyltransferase, DGAT, EC 2.3.1.22
Products: -
Products: -
?
additional information
?
-
-
Substrates: the multifunctional O-acetyltransferase is catalyzing the reactions of the acyl-CoA:retinol acyltransferase, of the monoacylglycerol transferase, EC 2.3.1.22, of the diacylglycerol transferase, EC 2.3.1.20, and of the wax synthase, EC 2.3.1.75, overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
-
Substrates: ARAT plays a role in retinol metabolism in tissues with low levels of cytosolic retinol binding protein or when cellular retinol concentrations are relatively high, thereby protecting cells from toxicity resulting from excess unesterified retinol
Products: -
Products: -
?
additional information
?
-
-
Substrates: the triacylglycerol synthesis enzyme DGAT1, EC 2.3.1.20, also catalyzes the synthesis of diacylglycerols, waxes, and retinyl esters, overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: DGAT1 is catalyzing the reactions of the monoacylglycerol transferase, EC 2.3.1.22, of the diacylglycerol transferase, EC 2.3.1.20, of the wax synthase, EC 2.3.1.75, and of the acyl-CoA:retinol acyltransferase, EC 2.3.1.76, overview
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
all-trans retinol + palmitoyl-CoA
all-trans-retinyl palmitate + CoA
-
Substrates: -
Products: -
Products: -
?
acyl-CoA + retinol
CoA + retinyl ester
-
Substrates: -
Products: -
Products: -
?
acyl-CoA + retinol
CoA + retinyl ester
-
Substrates: -
Products: -
Products: -
?
palmitoyl-CoA + 11-cis-retinol
CoA + 11-cis-retinyl palmitate
-
Substrates: -
Products: -
Products: -
r
palmitoyl-CoA + 11-cis-retinol
CoA + 11-cis-retinyl palmitate
-
Substrates: esterification of 11-cis-retinol is four times greater than esterification of all-trans-retinol in Muller cells
Products: -
Products: -
?
palmitoyl-CoA + all-trans-retinol
CoA + all-trans-retinyl palmitate
-
Substrates: -
Products: -
Products: -
r
palmitoyl-CoA + all-trans-retinol
CoA + all-trans-retinyl palmitate
-
Substrates: esterification of 11-cis-retinol is four times greater than esterification of all-trans-retinol in Muller cells
Products: -
Products: -
?
additional information
?
-
-
Substrates: ARAT may complement LRAT, EC 2.3.1.135, to provide additional retinyl-ester synthase activity under conditions of high all-trans-retinol
Products: -
Products: -
?
additional information
?
-
-
Substrates: the multifunctional O-acyltransferase likely plays an important role in lipid metabolism in human skin
Products: -
Products: -
?
additional information
?
-
-
Substrates: the multifunctional enzyme plays an important role in lipid metabolism in human skin
Products: -
Products: -
?
additional information
?
-
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
-
Substrates: ARAT plays a role in retinol metabolism in tissues with low levels of cytosolic retinol binding protein or when cellular retinol concentrations are relatively high, thereby protecting cells from toxicity resulting from excess unesterified retinol
Products: -
Products: -
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(6R)-6beta-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide phosphate
-
activity inhibited at 0.5%
cellular retinol-binding protein
-
specific inhibition of retinol fatty-acyltransferase by capturing substrate
-
XP620
-
selective isozyme DGAT1 inhibitor, inhibits the diacylglycerol acyltransferase and the retinol acyltransferase activities at the retinol recognition site, inhibition of 85% of retinyl ester production in intact differentiated Caco-2 cells, IC50: 88.7 nM
XP620
-
inhibits the ARAT activity of acyl coenzyme A:diacylglycerol acyltransferase isozyme 1 dependent on the retinol concentration in vivo and in vitro, IC50: 110 nM, no inhibition of isozyme 2 and acyl coenzyme A:monoacylglycerol acyltransferase isozyme 3, overview
additional information
-
not inhibited by 3,3',4,4'-tetrachlorobiphenyl
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
in presence of palmitoyl-CoA and CRALBP, Muller cell membranes synthesize 11-cis-retinyl ester from 11-cis-retinol at a rate which is 20-fold higher than that of all-trans-retinyl ester, in absence of CRALBP, 11-cis-retinyl ester synthesis is greatly reduced by 7-fold, in absence of palmitoyl-CoA, retinyl ester synthesis is not observed
-
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Neoplasms
Enhancement of acyl coenzyme A:retinol acyltransferase in rat liver and mammary tumor tissue by retinyl acetate and its competitive inhibition by N-(4-hydroxyphenyl) retinamide.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0139
palmitoyl-CoA
-
ARAT activity of recombinant acyl coenzyme A:diacylglycerol acyltransferase isozyme 1, pH 7.4, 37°C
0.0259
retinol
-
ARAT activity of recombinant acyl coenzyme A:diacylglycerol acyltransferase isozyme 1, pH 7.4, 37°C
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
-
inhibition kinetics depend highly on retinol concentration, overview, recombinant enzyme
-
0.00045
XP620
-
ARAT activity of acyl coenzyme A:diacylglycerol acyltransferase isozyme 1, pH 7.4, 37°C
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0000887
XP620
Homo sapiens
-
selective isozyme DGAT1 inhibitor, inhibits the diacylglycerol acyltransferase and the retinol acyltransferase activities at the retinol recognition site, inhibition of 85% of retinyl ester production in intact differentiated Caco-2 cells, IC50: 88.7 nM
0.00011
XP620
Homo sapiens
-
inhibits the ARAT activity of acyl coenzyme A:diacylglycerol acyltransferase isozyme 1 dependent on the retinol concentration in vivo and in vitro, IC50: 110 nM, no inhibition of isozyme 2 and acyl coenzyme A:monoacylglycerol acyltransferase isozyme 3, ov
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
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
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
squamous SCC12b and SCC13b lines are common type of skin cancer that has reduced capacity to esterify retinol relative to normal keratinocytes
brenda
additional information
-
neutral lipid synthesis enzyme acyl-CoA:diacylglycerol acyltransferase 1 functions as the major acyl-CoA:retinol acyltransferase
brenda
additional information
-
cells and tissues from DGAT1-deficient mice exhibit reduced ARAT activity
brenda
additional information
-
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
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
the enzyme is is very hydrophobic and has multiple predicted membrane-spanning domains
brenda
-
membrane fraction
-
brenda
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
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
Show AA Sequence and Transmembrane Helices (225 entries)
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Please use the AA Sequence and Transmembrane Helices Search for a specific query.
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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
additional information
-
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
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.4
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
partial purification by differential centrifugation
partial purification by differential centrifugation
-
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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 Spodoptera frugiperda Sf9 cell membranes using the baculovrisu transfection system
-
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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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
medicine
-
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
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Ross, A.C.
Retinol esterification by rat liver microsomes. Evidence for a fatty acyl coenzyme A: retinol acyltransferase
J. Biol. Chem.
257
2453-2459
1982
Felis silvestris, Rattus norvegicus, Rattus norvegicus Sprague-Dawley
brenda
Ball, M.D.
Acyl coenzyme A-dependent retinol esterification
Methods Enzymol.
189
446-449
1990
Rattus norvegicus
brenda
Ross, A.C.
Measurement of acyl coenzyme A-dependent esterification of retinol
Methods Enzymol.
189
442-445
1990
Rattus norvegicus
brenda
Saari, J.C.; Bredberg, D.L.
Acyl-CoA:retinol acyltransferase and lecithin:retinol acyltransferase activities of bovine retinal pigment epithelial microsomes
Methods Enzymol.
190
156-163
1990
Bos taurus
brenda
Chaudhary, L.R.; Nelson, E.C.
Some properties and subcellular distribution of acyl-coenzyme A: retinol acyltransferase activity in rat testes
Biochim. Biophys. Acta
917
24-32
1987
Rattus norvegicus, Rattus norvegicus Sprague-Dawley
brenda
MacDonald, P.N.; Ong, D.E.
Assay of lecithin-retinol acyltransferase
Methods Enzymol.
189
450-459
1990
Rattus norvegicus, Rattus norvegicus Sprague-Dawley
brenda
Nilsson, C.B.; Hanber, A.; Trossvik, C.; Haekansson, H.
2,3,7,8-Tetrachlorodibenzo-p-dioxin affects retinol esterification in rat hepatic stellate cells and kidney
Environ. Toxicol. Pharmacol.
2
17-23
1996
Rattus norvegicus, Rattus norvegicus Sprague-Dawley
brenda
Ross, A.C.; Kempner, E.S.
Radiation inactivation analysis of acyl-CoA:retinol acyltransferase and lecithin:retinol acyltransferase in rat liver
J. Lipid Res.
34
1201-1207
1993
Rattus norvegicus
brenda
Jurukovski, V.; Simon, M.
Reduced lecithin:retinol acyl transferase activity in cultured squamous cell carcinoma lines results in increased substrate-driven retinoic acid synthesis
Biochim. Biophys. Acta
1436
479-490
1999
Homo sapiens
brenda
Ndayibagira, A.; Spear, P.A.
Esterification and hydrolysis of vitamin A in the liver of brook trout (Salvelinus fontinalis) and the influence of a coplanar polychlorinated biphenyl
Comp. Biochem. Physiol. C
122C
317-325
1999
Salvelinus fontinalis
-
brenda
Kaschula, C.H.; Jin, M.H.; Desmond-Smith, N.S.; Travis, G.H.
Acyl CoA:retinol acyltransferase (ARAT) activity is present in bovine retinal pigment epithelium
Exp. Eye Res.
82
111-121
2005
Bos taurus, Homo sapiens
brenda
Yen, C.L.; Brown Iv, C.H.; Monetti, M.; Farese, R.V., Jr.
A human skin multifunctional O-acyltransferase that catalyzes the synthesis of acylglycerols, waxes, and retinyl esters
J. Lipid Res.
46
2388-2397
2005
Homo sapiens
brenda
Muniz, A.; Villazana-Espinoza, E.T.; Thackeray, B.; Tsin, A.T.
11-cis-Acyl-CoA:retinol O-acyltransferase activity in the primary culture of chicken Muller cells
Biochemistry
45
12265-12273
2006
Gallus gallus
brenda
Orland, M.D.; Anwar, K.; Cromley, D.; Chu, C.; Chen, L.; Billheimer, J.T.; Hussain, M.M.; Cheng, D.
Acyl coenzyme A dependent retinol esterification by acyl coenzyme A:diacylglycerol acyltransferase 1
Biochim. Biophys. Acta
1737
76-82
2005
Homo sapiens
brenda
Yen, C.L.; Monetti, M.; Burri, B.J.; Farese, R.V.
The triacylglycerol synthesis enzyme DGAT1 also catalyzes the synthesis of diacylglycerols, waxes, and retinyl esters
J. Lipid Res.
46
1502-1511
2005
Mus musculus
brenda
Shih, M.Y.; Kane, M.A.; Zhou, P.; Yen, C.L.; Streeper, R.S.; Napoli, J.L.; Farese, R.V.
Retinol esterification by DGAT1 is essential for retinoid homeostasis in murine skin
J. Biol. Chem.
284
4292-4299
2009
Mus musculus
brenda
EXTERNAL LINKS (specific for EC-Number 2.3.1.76)
Transporter Classification Database (TCDB): 2.A.50.4.1
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