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Chemical Compound Review

AGN-PC-00IWMO     [5-(6-aminopurin-9-yl)-4- hydroxy-2...

Synonyms: AG-F-04089, AC1L1AS8
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Disease relevance of tetradecanoyl-CoA


High impact information on tetradecanoyl-CoA


Biological context of tetradecanoyl-CoA


Anatomical context of tetradecanoyl-CoA


Associations of tetradecanoyl-CoA with other chemical compounds

  • Product inhibition studies indicate that Nmt1p has an ordered Bi Bi reaction mechanism with myristoyl-CoA binding to the apo-enzyme to form a high affinity binary complex followed by binding of peptide with subsequent release of CoA and then the myristoylpeptide product [21].
  • The nonhydrolyzable myristoyl-CoA analog, S-(2-oxopentadecyl)-CoA, blocked the GTP effect identically to myristoyl- and palmitoyl-CoA (IC50 = 0.5 microM); thus, fatty acyl transfer is not required, indicating that blockade is due to a direct allosteric modification of a component of the GTP-activated process by acyl-CoA esters [14].
  • Nmt1p transfers myristate (C14:0), from myristoyl-CoA to the amino-terminal Gly residue of several essential cellular proteins [22].
  • The acyl-CoA reductase had a high specificity for NADPH with a Km value of 5 microM at optimal concentrations of tetradecanoyl-CoA (5-10 microM) [23].
  • Incubation of purified NMT with [1-14C] myristoyl-CoA, followed by chymotryptic digestion, denaturing polyacrylamide gel electrophoresis, and treatment with hydroxylamine yielded results that are highly suggestive of a covalent ester-linked acyl-enzyme complex [24].

Gene context of tetradecanoyl-CoA


Analytical, diagnostic and therapeutic context of tetradecanoyl-CoA


  1. Comparison of the acyl chain specificities of human myristoyl-CoA synthetase and human myristoyl-CoA:protein N-myristoyltransferase. Kishore, N.S., Wood, D.C., Mehta, P.P., Wade, A.C., Lu, T., Gokel, G.W., Gordon, J.I. J. Biol. Chem. (1993) [Pubmed]
  2. Substrate specificity of Saccharomyces cerevisiae myristoyl-CoA: protein N-myristoyltransferase. Analysis of fatty acid analogs containing carbonyl groups, nitrogen heteroatoms, and nitrogen heterocycles in an in vitro enzyme assay and subsequent identification of inhibitors of human immunodeficiency virus I replication. Devadas, B., Lu, T., Katoh, A., Kishore, N.S., Wade, A.C., Mehta, P.P., Rudnick, D.A., Bryant, M.L., Adams, S.P., Li, Q. J. Biol. Chem. (1992) [Pubmed]
  3. Crystal structure of the Mycobacterium tuberculosis beta-ketoacyl-acyl carrier protein synthase III. Scarsdale, J.N., Kazanina, G., He, X., Reynolds, K.A., Wright, H.T. J. Biol. Chem. (2001) [Pubmed]
  4. Characterization of a polyhistidine-tagged form of human myristoyl-CoA: protein N-myristoyltransferase produced in Escherichia coli. McIlhinney, R.A., Patel, P.B., McGlone, K. Eur. J. Biochem. (1994) [Pubmed]
  5. Rat liver peroxisomal and mitochondrial fatty acid oxidation in sepsis. Yamamoto, T. Surgery today. (1993) [Pubmed]
  6. Myristic acid auxotrophy caused by mutation of S. cerevisiae myristoyl-CoA:protein N-myristoyltransferase. Duronio, R.J., Rudnick, D.A., Johnson, R.L., Johnson, D.R., Gordon, J.I. J. Cell Biol. (1991) [Pubmed]
  7. Targeted gene replacement demonstrates that myristoyl-CoA: protein N-myristoyltransferase is essential for viability of Cryptococcus neoformans. Lodge, J.K., Jackson-Machelski, E., Toffaletti, D.L., Perfect, J.R., Gordon, J.I. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  8. The 31-kDa precursor of interleukin 1 alpha is myristoylated on specific lysines within the 16-kDa N-terminal propiece. Stevenson, F.T., Bursten, S.L., Fanton, C., Locksley, R.M., Lovett, D.H. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  9. 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]
  10. Cloning, expression, and characterization of the acyl-CoA-binding protein in African trypanosomes. Milne, K.G., Ferguson, M.A. J. Biol. Chem. (2000) [Pubmed]
  11. Altered membrane association of p60v-src and a murine 63-kDa N-myristoyl protein after incorporation of an oxygen-substituted analog of myristic acid. Heuckeroth, R.O., Gordon, J.I. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  12. Differential acylation in vitro with tetradecanoyl coenzyme A and tetradecanoic acid (+ATP) of three polypeptides shown to have induced synthesis in Photobacterium phosphoreum. Wall, L., Rodriquez, A., Meighen, E. J. Biol. Chem. (1984) [Pubmed]
  13. Purification and characterization of a bioluminescence-related fatty acyl esterase from Vibrio harveyi. Byers, D., Meighen, E. J. Biol. Chem. (1985) [Pubmed]
  14. Modification of GTP-activated calcium translocation by fatty acyl-CoA esters. Evidence for a GTP-induced prefusion event. Rys-Sikora, K.E., Ghosh, T.K., Gill, D.L. J. Biol. Chem. (1994) [Pubmed]
  15. The substrate specificity of Saccharomyces cerevisiae myristoyl-CoA: protein N-myristoyltransferase. Polar probes of the enzyme's myristoyl-CoA recognition site. Lu, T., Li, Q., Katoh, A., Hernandez, J., Duffin, K., Jackson-Machelski, E., Knoll, L.J., Gokel, G.W., Gordon, J.I. J. Biol. Chem. (1994) [Pubmed]
  16. Crystal structure of the anti-fungal target N-myristoyl transferase. Weston, S.A., Camble, R., Colls, J., Rosenbrock, G., Taylor, I., Egerton, M., Tucker, A.D., Tunnicliffe, A., Mistry, A., Mancia, F., de la Fortelle, E., Irwin, J., Bricogne, G., Pauptit, R.A. Nat. Struct. Biol. (1998) [Pubmed]
  17. A role for Saccharomyces cerevisiae fatty acid activation protein 4 in regulating protein N-myristoylation during entry into stationary phase. Ashrafi, K., Farazi, T.A., Gordon, J.I. J. Biol. Chem. (1998) [Pubmed]
  18. Myristoyl-coA:protein N-myristoyltransferase from bovine cardiac muscle: molecular cloning, kinetic analysis, and in vitro proteolytic cleavage by m-calpain. Raju, R.V., Kakkar, R., Datla, R.S., Radhi, J., Sharma, R.K. Exp. Cell Res. (1998) [Pubmed]
  19. Immunocytochemical characterization and subcellular localization of human myristoyl-CoA: protein N-myristoyltransferase in HeLa cells. McIlhinney, R.A., McGlone, K. Exp. Cell Res. (1996) [Pubmed]
  20. Effect of membrane environment on the activity and inhibitability by malonyl-CoA of the carnitine acyltransferase of hepatic microsomal membranes. Broadway, N.M., Saggerson, E.D. Biochem. J. (1997) [Pubmed]
  21. Isothermal titration calorimetric studies of Saccharomyces cerevisiae myristoyl-CoA:protein N-myristoyltransferase. Determinants of binding energy and catalytic discrimination among acyl-CoA and peptide ligands. Bhatnagar, R.S., Jackson-Machelski, E., McWherter, C.A., Gordon, J.I. J. Biol. Chem. (1994) [Pubmed]
  22. Genetic analysis of the role of Saccharomyces cerevisiae acyl-CoA synthetase genes in regulating protein N-myristoylation. Johnson, D.R., Knoll, L.J., Rowley, N., Gordon, J.I. J. Biol. Chem. (1994) [Pubmed]
  23. Purification of the acyl coenzyme A reductase component from a complex responsible for the reduction of fatty acids in bioluminescent bacteria. Properties and acyltransferase activity. Rodriguez, A., Riendeau, D., Meighen, E. J. Biol. Chem. (1983) [Pubmed]
  24. Structural and functional studies of Saccharomyces cerevisiae myristoyl-CoA:protein N-myristoyltransferase produced in Escherichia coli. Evidence for an acyl-enzyme intermediate. Rudnick, D.A., McWherter, C.A., Adams, S.P., Ropson, I.J., Duronio, R.J., Gordon, J.I. J. Biol. Chem. (1990) [Pubmed]
  25. Use of photoactivatable peptide substrates of Saccharomyces cerevisiae myristoyl-CoA:protein N-myristoyltransferase (Nmt1p) to characterize a myristoyl-CoA-Nmt1p-peptide ternary complex and to provide evidence for an ordered reaction mechanism. Rudnick, D.A., Rocque, W.J., McWherter, C.A., Toth, M.V., Jackson-Machelski, E., Gordon, J.I. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  26. N-myristoylation of Arf proteins in Candida albicans: an in vivo assay for evaluating antifungal inhibitors of myristoyl-CoA: protein N-myristoyltransferase. Lodge, J.K., Jackson-Machelski, E., Devadas, B., Zupec, M.E., Getman, D.P., Kishore, N., Freeman, S.K., McWherter, C.A., Sikorski, J.A., Gordon, J.I. Microbiology (Reading, Engl.) (1997) [Pubmed]
  27. Vitamin D3 inhibits fatty acid synthase expression by stimulating the expression of long-chain fatty-acid-CoA ligase 3 in prostate cancer cells. Qiao, S., Tuohimaa, P. FEBS Lett. (2004) [Pubmed]
  28. Myristoylation-dependent N-terminal cleavage of the myristoylated alanine-rich C kinase substrate (MARCKS) by cellular extracts. Braun, T., McIlhinney, R.A., Vergères, G. Biochimie (2000) [Pubmed]
  29. Sequence and expression of Drosophila myristoyl-CoA: protein N-myristoyl transferase: evidence for proteolytic processing and membrane localisation. Ntwasa, M., Egerton, M., Gay, N.J. J. Cell. Sci. (1997) [Pubmed]
  30. Influence of moderate temperatures on myristoyl-CoA metabolism and acyl-CoA thioesterase activity in the psychrophilic antarctic yeast Rhodotorula aurantiaca. Sabri, A., Bare, G., Jacques, P., Jabrane, A., Ongena, M., Van Heugen, J.C., Devreese, B., Thonart, P. J. Biol. Chem. (2001) [Pubmed]
  31. Purification and partial sequencing of myristoyl-CoA:protein N-myristoyltransferase from bovine brain. McIlhinney, R.A., McGlone, K., Willis, A.C. Biochem. J. (1993) [Pubmed]
  32. Characterization of Type I and Type II myristoyl-CoA:protein N-myristoyltransferases with the Acyl-CoAs found on heterogeneously acylated retinal proteins. Rundle, D.R., Rajala, R.V., Anderson, R.E. Exp. Eye Res. (2002) [Pubmed]
  33. Crystallographic phasing of myristoyl-CoA-protein N-myristoyltransferase using an iodinated analog of myristoyl-CoA. Fütterer , K., Murray , C.L., Bhatnagar , R.S., Gokel , G.W., Gordon , J.I., Waksman , G. Acta Crystallogr. D Biol. Crystallogr. (2001) [Pubmed]
  34. Thermodynamic studies of myristoyl-CoA: protein N-myristoyltransferase using isothermal titration calorimetry. Bhatnagar, R.S., Gordon, J.I. Meth. Enzymol. (1995) [Pubmed]
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