The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

C00510     [(2R,3R,4R,5R)-5-(6- aminopurin-9-yl)-4...

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of C00510


High impact information on C00510


Biological context of C00510

  • When expressed from a 2-mu plasmid, Fat1p contributes significant oleoyl-CoA synthetase activity, which indicates vectorial esterification and metabolic trapping are the driving forces behind import [9].
  • MGAT2 enzyme expressed in COS-7 cells displayed a broad range of substrate specificity toward fatty acyl-CoA derivatives and monoacylglycerols, among which the highest activities were observed with oleoyl-CoA and rac-1-monolauroylglycerol, respectively [10].
  • The methylated product was apparently formed by tissue as follows: (a) cleavage of oleoyl-CoA by an amidase to form S-oleoylmercaptoethylamine; (b) spontaneous rearrangement to form N-oleoylmercaptoethylamide; and (c) enzymatic methylation of the free thiol by AdoMet [11].
  • Taken together, our observations demonstrate that the oleoyl-CoA and palmitoleyl-CoA produced by SCD1 are necessary to synthesize enough cholesterol esters and triglycerides in the liver and suggest that regulation of SCD1 activity plays an important role in mechanisms of cellular cholesterol homeostasis [12].
  • The mrACBP was functionally active as shown by binding of cis-parinaroyl-CoA with high affinity, K(d) = 12 +/- 2 nM, at a single binding site, stimulating oleoyl-CoA utilization by microsomal glycerol-3-phosphate acyltransferase 3.2-fold and protecting oleoyl-CoA from microsomal acyl-CoA hydrolase [13].

Anatomical context of C00510

  • Addition of oleoyl-CoA to incubations containing rat lung membranes and S-adenosyl [methyl-3H]methionine resulted in the formation of a previously unidentified nonpolar methylated lipid [11].
  • Intact red blood cells formed the nonpolar methylated lipid intracellularly upon incubation with [methyl-3H]methionine and oleoyl-CoA [11].
  • The stepwise oxidation of beta-apocarotenoic acid in mitochondria was dose-related to both protein concentration and substrate concentration. beta-Apocarotenoic acid oxidation was inhibited in a dose-dependent manner when it was co-incubated with oleoyl-CoA [14].
  • Oleoyl-CoA is the major de novo product of stearoyl-CoA desaturase 1 gene isoform and substrate for the biosynthesis of the Harderian gland 1-alkyl-2,3-diacylglycerol [15].
  • Regulation of oleoyl-CoA synthesis in the peripheral nervous system: demonstration of a link with myelin synthesis [16].

Associations of C00510 with other chemical compounds

  • Products obtained from oleoyl-CoA or palmitoyl-CoA, incubated with nonradioactive or [methyl-14C]AdoMet, were compared using electron impact and/or chemical ionization mass spectrometry [11].
  • Kinetic analyses of LPGAT1 expressed in COS-7 cells showed that oleoyl-LPG was preferred over palmitoyl-LPG as an acyl receptor, whereas oleoyl-CoA was preferred over lauroyl-CoA as an acyl donor [7].
  • While the in vitro binding of a photoreactive fatty acid, 11-m-diazirinophenoxy[11-3H]undecanoate, to a cytoplasmic fatty acid-binding protein was insensitive to changes in pH from pH 7.5 to 5.5, the in vitro conversion of oleate into oleoyl-CoA by cellular acyl-CoA synthetase decreased dramatically [17].
  • 5. Attempts to demonstrate the presence of an oleoyl-CoA desaturase in safflower microsomal fractions by the appearance of linoleoyl-CoA in reaction mixtures were inconclusive [18].
  • Microsomal preparations from developing embryos at the mid-stage of TAG accumulation catalysed the acylation of [14C]glycerol 3-phosphate with either decanoyl-CoA or oleoyl-CoA, resulting in the formation of phosphatidic acid (PtdOH), DAG and TAG [19].

Gene context of C00510


Analytical, diagnostic and therapeutic context of C00510

  • When the 'microsomal fraction' of rat mucosa was incubated with [3H]retinol and palmitoyl-CoA or oleoyl-CoA, [3H]retinyl esters were formed as identified by alumina column chromatography and reverse phase high-pressure liquid chromatography (HPLC) [25].
  • As determined by spectrofluorometric titration, binding affinities for palmitoyl-, stearoyl-, and oleoyl-CoA (Kd = 0.2-0.4 microM) are 5-10 times lower than those for the corresponding nonesterified fatty acids [26].
  • Indeed, incubation of cytosol fraction alone with oleate or oleoyl-CoA at 37 degrees C, followed by centrifugation, induces a significant increase (sevenfold) in PAP-1 activity in the pellet fraction [27].


  1. Substrate specificity modification of the stromal glycerol-3-phosphate acyltransferase. Ferri, S.R., Toguri, T. Arch. Biochem. Biophys. (1997) [Pubmed]
  2. Metabolism of oleoyl-CoA in rat brain synaptosomes: effects of calcium and post-decapitative ischemia. Strosznajder, J., Tang, W., Manning, R., Lin, A.Y., MacQuarrie, R., Sun, G.Y. Neurochem. Res. (1981) [Pubmed]
  3. Acyl-coenzyme A:cholesterol acyltransferase in human liver. In vitro detection and some characteristics of the enzyme. Erickson, S.K., Cooper, A.D. Metab. Clin. Exp. (1980) [Pubmed]
  4. Effect of fatty acids and their derivatives on mitochondrial structures. Singh, A.K., Yoshida, Y., Garvin, A.J., Singh, I. J. Exp. Pathol. (1989) [Pubmed]
  5. Inhibition of citrate synthase by oleoyl-CoA: a regulatory phenomenon. Hsu, K.H., Powell, G.L. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  6. Highly selective hydrolysis of fatty acyl-CoAs by calcium-independent phospholipase A2beta. Enzyme autoacylation and acyl-CoA-mediated reversal of calmodulin inhibition of phospholipase A2 activity. Jenkins, C.M., Yan, W., Mancuso, D.J., Gross, R.W. J. Biol. Chem. (2006) [Pubmed]
  7. Identification and characterization of a gene encoding human LPGAT1, an endoplasmic reticulum-associated lysophosphatidylglycerol acyltransferase. Yang, Y., Cao, J., Shi, Y. J. Biol. Chem. (2004) [Pubmed]
  8. Leaky beta-oxidation of a trans-fatty acid: incomplete beta-oxidation of elaidic acid is due to the accumulation of 5-trans-tetradecenoyl-CoA and its hydrolysis and conversion to 5-trans-tetradecenoylcarnitine in the matrix of rat mitochondria. Yu, W., Liang, X., Ensenauer, R.E., Vockley, J., Sweetman, L., Schulz, H. J. Biol. Chem. (2004) [Pubmed]
  9. Vectorial acylation in Saccharomyces cerevisiae. Fat1p and fatty acyl-CoA synthetase are interacting components of a fatty acid import complex. Zou, Z., Tong, F., Faergeman, N.J., Børsting, C., Black, P.N., DiRusso, C.C. J. Biol. Chem. (2003) [Pubmed]
  10. Properties of the mouse intestinal acyl-CoA:monoacylglycerol acyltransferase, MGAT2. Cao, J., Burn, P., Shi, Y. J. Biol. Chem. (2003) [Pubmed]
  11. Biosynthesis of S-methyl-N-oleoylmercaptoethylamide from oleoyl coenzyme A and S-adenosylmethionine. Zatz, M., Engelsen, S.J., Markey, S.P. J. Biol. Chem. (1982) [Pubmed]
  12. The biosynthesis of hepatic cholesterol esters and triglycerides is impaired in mice with a disruption of the gene for stearoyl-CoA desaturase 1. Miyazaki, M., Kim, Y.C., Gray-Keller, M.P., Attie, A.D., Ntambi, J.M. J. Biol. Chem. (2000) [Pubmed]
  13. Membrane charge and curvature determine interaction with acyl-CoA binding protein (ACBP) and fatty acyl-CoA targeting. Chao, H., Martin, G.G., Russell, W.K., Waghela, S.D., Russell, D.H., Schroeder, F., Kier, A.B. Biochemistry (2002) [Pubmed]
  14. Beta-oxidation in rabbit liver in vitro and in the perfused ferret liver contributes to retinoic acid biosynthesis from beta-apocarotenoic acids. Wang, X.D., Russell, R.M., Liu, C., Stickel, F., Smith, D.E., Krinsky, N.I. J. Biol. Chem. (1996) [Pubmed]
  15. Oleoyl-CoA is the major de novo product of stearoyl-CoA desaturase 1 gene isoform and substrate for the biosynthesis of the Harderian gland 1-alkyl-2,3-diacylglycerol. Miyazaki, M., Kim, H.J., Man, W.C., Ntambi, J.M. J. Biol. Chem. (2001) [Pubmed]
  16. Regulation of oleoyl-CoA synthesis in the peripheral nervous system: demonstration of a link with myelin synthesis. Garbay, B., Boiron-Sargueil, F., Shy, M., Chbihi, T., Jiang, H., Kamholz, J., Cassagne, C. J. Neurochem. (1998) [Pubmed]
  17. The effect of intracellular pH on long-chain fatty acid uptake in 3T3-L1 adipocytes: evidence that uptake involves the passive diffusion of protonated long-chain fatty acids across the plasma membrane. Trigatti, B.L., Gerber, G.E. Biochem. J. (1996) [Pubmed]
  18. Evidence for an oleoyl phosphatidylcholine desaturase in microsomal preparations from cotyledons of safflower (Carthamus tinctorius) seed. Slack, C.R., Roughan, P.G., Browse, J. Biochem. J. (1979) [Pubmed]
  19. Regulation of triacylglycerol biosynthesis in embryos and microsomal preparations from the developing seeds of Cuphea lanceolata. Bafor, M., Jonsson, L., Stobart, A.K., Stymne, S. Biochem. J. (1990) [Pubmed]
  20. Differential modulation of ACAT1 and ACAT2 transcription and activity by long chain free fatty acids in cultured cells. Seo, T., Oelkers, P.M., Giattina, M.R., Worgall, T.S., Sturley, S.L., Deckelbaum, R.J. Biochemistry (2001) [Pubmed]
  21. Ablation of the liver fatty acid binding protein gene decreases fatty acyl CoA binding capacity and alters fatty acyl CoA pool distribution in mouse liver. Martin, G.G., Huang, H., Atshaves, B.P., Binas, B., Schroeder, F. Biochemistry (2003) [Pubmed]
  22. The effect of charge reversal mutations in the alpha-helical region of liver fatty acid binding protein on the binding of fatty-acyl CoAs, lysophospholipids and bile acids. Hagan, R.M., Davies, J.K., Wilton, D.C. Mol. Cell. Biochem. (2002) [Pubmed]
  23. Analysis of the ligand binding properties of recombinant bovine liver-type fatty acid binding protein. Rolf, B., Oudenampsen-Krüger, E., Börchers, T., Faergeman, N.J., Knudsen, J., Lezius, A., Spener, F. Biochim. Biophys. Acta (1995) [Pubmed]
  24. Long-chain acyl-CoA esters and phosphatidylinositol phosphates modulate ATP inhibition of KATP channels by the same mechanism. Schulze, D., Rapedius, M., Krauter, T., Baukrowitz, T. J. Physiol. (Lond.) (2003) [Pubmed]
  25. Acyl CoA:retinol acyltransferase in rat small intestine: its activity and some properties of the enzymic reaction. Helgerud, P., Petersen, L.B., Norum, K.R. J. Lipid Res. (1982) [Pubmed]
  26. Continuous recording of long-chain acyl-coenzyme a synthetase activity using fluorescently labeled bovine serum albumin. Demant, E.J., Nystrøm, B.T. Anal. Biochem. (2001) [Pubmed]
  27. Relationship between the inhibition of phosphatidic acid phosphohydrolase-1 by oleate and oleoyl-CoA ester and its apparent translocation. Elabbadi, N., Day, C.P., Gamouh, A., Zyad, A., Yeaman, S.J. Biochimie (2005) [Pubmed]
WikiGenes - Universities