myristic acid

Summary

Summary: A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed)

Top Publications

  1. Benetka W, Mehlmer N, Maurer Stroh S, Sammer M, Koranda M, Neumüller R, et al. Experimental testing of predicted myristoylation targets involved in asymmetric cell division and calcium-dependent signalling. Cell Cycle. 2008;7:3709-19 pubmed
  2. Podell S, Gribskov M. Predicting N-terminal myristoylation sites in plant proteins. BMC Genomics. 2004;5:37 pubmed
    ..The new model has been used to predict 589 plant proteins likely to contain N-terminal myristoylation signals, and to analyze the functional families in which these proteins occur. ..
  3. Colombo S, Longhi R, Alcaro S, Ortuso F, Sprocati T, Flora A, et al. N-myristoylation determines dual targeting of mammalian NADH-cytochrome b5 reductase to ER and mitochondrial outer membranes by a mechanism of kinetic partitioning. J Cell Biol. 2005;168:735-45 pubmed
    ..Thus, competition between two cotranslational events, binding of signal recognition particle and modification by N-myristoylation, determines the site of translation and the localization of b5R. ..
  4. Sakurai N, Moriya K, Suzuki T, Sofuku K, Mochiki H, Nishimura O, et al. Detection of co- and posttranslational protein N-myristoylation by metabolic labeling in an insect cell-free protein synthesis system. Anal Biochem. 2007;362:236-44 pubmed
    ..results showed that in vitro translation of cDNA coding for N-myristoylated protein in the presence of [(3)H]myristic acid followed by SDS-PAGE and fluorography is a useful method for rapid detection of protein N-myristoylation...
  5. Narasimhan B, Mourya V, Dhake A. Design, synthesis, antibacterial, and QSAR studies of myristic acid derivatives. Bioorg Med Chem Lett. 2006;16:3023-9 pubmed
    A series of esters and amides of myristic acid was synthesized and tested in vitro for antibacterial activity against gram-positive and gram-negative bacteria...
  6. Suzuki T, Moriya K, Nagatoshi K, Ota Y, Ezure T, Ando E, et al. Strategy for comprehensive identification of human N-myristoylated proteins using an insect cell-free protein synthesis system. Proteomics. 2010;10:1780-93 pubmed publisher
  7. Liu C, Huang H. Antimicrobial activity of curcumin-loaded myristic acid microemulsions against Staphylococcus epidermidis. Chem Pharm Bull (Tokyo). 2012;60:1118-24 pubmed
    The bactericidal properties of myristic acid and curcumin were revealed in a number of studies...
  8. Sakurai N, Utsumi T. Posttranslational N-myristoylation is required for the anti-apoptotic activity of human tGelsolin, the C-terminal caspase cleavage product of human gelsolin. J Biol Chem. 2006;281:14288-95 pubmed
    ..apoptosis, metabolic labeling of gelsolin and its caspase cleavage products expressed in COS-1 cells with [3H]myristic acid was performed...
  9. Beauchamp E, Goenaga D, le Bloc h J, Catheline D, Legrand P, Rioux V. Myristic acid increases the activity of dihydroceramide Delta4-desaturase 1 through its N-terminal myristoylation. Biochimie. 2007;89:1553-61 pubmed
    ..the activity of wild-type DES1 was also linearly increased in the presence of increased concentrations of myristic acid incubated with the cells. These results demonstrate that DES1 is a newly discovered myristoylated protein...

More Information

Publications61

  1. Lin C, Li C, Huang P, Lee F. A developmentally regulated ARF-like 5 protein (ARL5), localized to nuclei and nucleoli, interacts with heterochromatin protein 1. J Cell Sci. 2002;115:4433-45 pubmed
    ..Our findings suggest that developmentally regulated ARL5, with its distinctive nuclear/nucleolar localization and interaction with HP1alpha, may play a role(s) in nuclear dynamics and/or signaling cascades during embryonic development. ..
  2. Cembran A, Masterson L, McClendon C, Taylor S, Gao J, Veglia G. Conformational equilibrium of N-myristoylated cAMP-dependent protein kinase A by molecular dynamics simulations. Biochemistry. 2012;51:10186-96 pubmed publisher
    ..These results support a role of N-myristoylation in the allosteric regulation of PKA-C. ..
  3. Rioux V, Pedrono F, Legrand P. Regulation of mammalian desaturases by myristic acid: N-terminal myristoylation and other modulations. Biochim Biophys Acta. 2011;1811:1-8 pubmed publisher
    b>Myristic acid, the 14-carbon saturated fatty acid (C14:0), usually accounts for small amounts (0.5%-1% weight of total fatty acids) in animal tissues...
  4. Perez M, Greenwald D, de la Torre J. Myristoylation of the RING finger Z protein is essential for arenavirus budding. J Virol. 2004;78:11443-8 pubmed
    ..Metabolic labeling showed incorporation of [(3)H]myristic acid by wild-type Z protein but not by the G2A mutant. The mutation G2A eliminated Z-mediated budding...
  5. Zöllner A, Dragan C, Pistorius D, Muller R, Bode H, Peters F, et al. Human CYP4Z1 catalyzes the in-chain hydroxylation of lauric acid and myristic acid. Biol Chem. 2009;390:313-7 pubmed publisher
    ..and demonstrate by whole-cell biotransformation assays CYP4Z1-dependent in-chain hydroxylation of lauric and myristic acid, which in both cases leads to the formation of four different monohydroxylated products at positions omega-2, ..
  6. Soliva C, Meile L, Cieslak A, Kreuzer M, Machmüller A. Rumen simulation technique study on the interactions of dietary lauric and myristic acid supplementation in suppressing ruminal methanogenesis. Br J Nutr. 2004;92:689-700 pubmed
    The interactions of lauric (C12) and myristic acid (C14) in suppressing ruminal methanogenesis and methanogens were investigated with the rumen simulation technique (Rusitec) using bovine ruminal fluid...
  7. Isenberg J, Jia Y, Fukuyama J, Switzer C, Wink D, Roberts D. Thrombospondin-1 inhibits nitric oxide signaling via CD36 by inhibiting myristic acid uptake. J Biol Chem. 2007;282:15404-15 pubmed
    ..Based on evidence that myristic acid and TSP1 each modulate endothelial cell nitric oxide signaling in a CD36-dependent manner, we examined the ..
  8. Olivetta E, Percario Z, Fiorucci G, Mattia G, Schiavoni I, Dennis C, et al. HIV-1 Nef induces the release of inflammatory factors from human monocyte/macrophages: involvement of Nef endocytotic signals and NF-kappa B activation. J Immunol. 2003;170:1716-27 pubmed
    ..Our data add new hints supporting the idea that the presence of Nef is per se heavily detrimental for monocyte/macrophages and relative cross-talking cell types. ..
  9. Cordeddu V, Di Schiavi E, Pennacchio L, Ma ayan A, Sarkozy A, Fodale V, et al. Mutation of SHOC2 promotes aberrant protein N-myristoylation and causes Noonan-like syndrome with loose anagen hair. Nat Genet. 2009;41:1022-6 pubmed publisher
    ..These results document the first example of an acquired N-terminal lipid modification of a protein causing human disease...
  10. Senin I, Fischer T, Komolov K, Zinchenko D, Philippov P, Koch K. Ca2+-myristoyl switch in the neuronal calcium sensor recoverin requires different functions of Ca2+-binding sites. J Biol Chem. 2002;277:50365-72 pubmed
    ..We discuss this mechanism as one critical step for inhibition of rhodopsin kinase by recoverin. ..
  11. Soliva C, Hindrichsen I, Meile L, Kreuzer M, Machmuller A. Effects of mixtures of lauric and myristic acid on rumen methanogens and methanogenesis in vitro. Lett Appl Microbiol. 2003;37:35-9 pubmed
    ..The results support strategies for an environment-friendly ruminant nutrition as it was demonstrated that part of the less palatable C12 could be replaced by C14 without losing its methane-suppressing potential. ..
  12. Mangino G, Percario Z, Fiorucci G, Vaccari G, Manrique S, Romeo G, et al. In vitro treatment of human monocytes/macrophages with myristoylated recombinant Nef of human immunodeficiency virus type 1 leads to the activation of mitogen-activated protein kinases, IkappaB kinases, and interferon regulatory factor 3 and to the r. J Virol. 2007;81:2777-91 pubmed
    ..In addition, we have observed the activation of interferon regulatory factor 3, leading to the synthesis of beta interferon mRNA and protein, which in turn induces STAT2 phosphorylation. All of these effects require Nef myristoylation. ..
  13. Heal W, Wickramasinghe S, Leatherbarrow R, Tate E. N-Myristoyl transferase-mediated protein labelling in vivo. Org Biomol Chem. 2008;6:2308-15 pubmed publisher
    ..The straightforward synthesis of the chemical and molecular biological tools described should enable their use in a wide range of N-terminal labelling applications. ..
  14. Price H, Panethymitaki C, Goulding D, Smith D. Functional analysis of TbARL1, an N-myristoylated Golgi protein essential for viability in bloodstream trypanosomes. J Cell Sci. 2005;118:831-41 pubmed
    ..Our results suggest that there may be different pathways regulating Golgi structure and function in the two major life cycle stages of T. brucei. ..
  15. Jan S, Guillou H, D Andrea S, Daval S, Bouriel M, Rioux V, et al. Myristic acid increases delta6-desaturase activity in cultured rat hepatocytes. Reprod Nutr Dev. 2004;44:131-40 pubmed
    ..4 mg. Data showed that cell treatment with 0.5 mmol x L(-1) myristic acid during 43 h specifically increased delta6-desaturase activity...
  16. Pierre M, Traverso J, Boisson B, Domenichini S, Bouchez D, Giglione C, et al. N-myristoylation regulates the SnRK1 pathway in Arabidopsis. Plant Cell. 2007;19:2804-21 pubmed
    ..We show here that protein N-myristoylation is systematically associated with shoot meristem development and that SnRK1 (for SNF1-related kinase) is one of its essential primary targets. ..
  17. Beauchamp E, Tekpli X, Marteil G, Lagadic Gossmann D, Legrand P, Rioux V. N-Myristoylation targets dihydroceramide Delta4-desaturase 1 to mitochondria: partial involvement in the apoptotic effect of myristic acid. Biochimie. 2009;91:1411-9 pubmed publisher
    This study was designed to analyze the effect of myristic acid on ceramide synthesis and its related lipoapoptosis pathway...
  18. Burnaevskiy N, Fox T, Plymire D, Ertelt J, Weigele B, Selyunin A, et al. Proteolytic elimination of N-myristoyl modifications by the Shigella virulence factor IpaJ. Nature. 2013;496:106-9 pubmed publisher
    ..Taken together, these findings show a previously unrecognized pathogenic mechanism for the site-specific elimination of N-myristoyl protein modification...
  19. Yamauchi S, Fusada N, Hayashi H, Utsumi T, Uozumi N, Endo Y, et al. The consensus motif for N-myristoylation of plant proteins in a wheat germ cell-free translation system. FEBS J. 2010;277:3596-607 pubmed publisher
    ..We have thus shown that a wheat germ cell-free system is a useful tool for plant N-myristoylome analysis. This in vitro approach will facilitate comprehensive determination of N-myristoylated proteins in plants. ..
  20. Ezanno H, Le Bloc h J, Beauchamp E, Lagadic Gossmann D, Legrand P, Rioux V. Myristic acid increases dihydroceramide Δ4-desaturase 1 (DES1) activity in cultured rat hepatocytes. Lipids. 2012;47:117-28 pubmed publisher
    ..It was previously observed that myristic acid binds DES1 through N-myristoylation...
  21. Bastidas A, Deal M, Steichen J, Keshwani M, Guo Y, Taylor S. Role of N-terminal myristylation in the structure and regulation of cAMP-dependent protein kinase. J Mol Biol. 2012;422:215-29 pubmed publisher
  22. Maurer Stroh S, Gouda M, Novatchkova M, Schleiffer A, Schneider G, Sirota F, et al. MYRbase: analysis of genome-wide glycine myristoylation enlarges the functional spectrum of eukaryotic myristoylated proteins. Genome Biol. 2004;5:R21 pubmed
    ..Furthermore, we classify five membrane-attachment factors that occur most frequently in combination with, or even replacing, myristoyl anchors, as some protein family examples show. ..
  23. Bradbury K, Skeaff C, Green T, Gray A, Crowe F. The serum fatty acids myristic acid and linoleic acid are better predictors of serum cholesterol concentrations when measured as molecular percentages rather than as absolute concentrations. Am J Clin Nutr. 2010;91:398-405 pubmed publisher
    ..To advance understanding about this fundamental concept, we examined the ability of serum myristic acid and linoleic acid, expressed as molecular percentages or as concentrations, to predict dietary fat and serum ..
  24. Veeresh Babu S, Veeresh B, Patil A, Warke Y. Lauric acid and myristic acid prevent testosterone induced prostatic hyperplasia in rats. Eur J Pharmacol. 2010;626:262-5 pubmed publisher
    ..Major components of those plants were lauric acid and myristic acid. Our study investigated whether lauric acid or myristic acid prevent testosterone induced prostatic ..
  25. Maroun C, Naujokas M, Park M. Membrane targeting of Grb2-associated binder-1 (Gab1) scaffolding protein through Src myristoylation sequence substitutes for Gab1 pleckstrin homology domain and switches an epidermal growth factor response to an invasive morphogenic program. Mol Biol Cell. 2003;14:1691-708 pubmed
    ..These results suggest that the subcellular localization of Gab1 is a critical determinant for epithelial morphogenesis and invasiveness. ..
  26. Hwang J, Koch K. Calcium- and myristoyl-dependent properties of guanylate cyclase-activating protein-1 and protein-2. Biochemistry. 2002;41:13021-8 pubmed
    ..Thus, the myristoyl group controls the Ca2+-sensitivity of GCAP-1 (not that of GCAP-2) by an allosteric mechanism, but this control step does not involve a myristoyl switch. ..
  27. Panjarian S, Iacob R, Chen S, Wales T, Engen J, Smithgall T. Enhanced SH3/linker interaction overcomes Abl kinase activation by gatekeeper and myristic acid binding pocket mutations and increases sensitivity to small molecule inhibitors. J Biol Chem. 2013;288:6116-29 pubmed publisher
    ..with chronic myelogenous leukemia to small molecule inhibitors that target either the active site or the myristic acid binding pocket in the kinase domain C-lobe...
  28. Dumonceaux T, Rajala R, Sharma R, Selvaraj G, Datla R. Molecular characterization of a gene encoding N-myristoyl transferase (NMT) from Triticum aestivum (bread wheat). Genome. 2004;47:1036-42 pubmed publisher
    ..3.1.97) acylates the Gly residue abutting the N-terminal Met with a myristic acid following the removal of the Met residue in certain eukaryotic proteins, and in some cases myristoylation is ..
  29. Martin D, Beauchamp E, Berthiaume L. Post-translational myristoylation: Fat matters in cellular life and death. Biochimie. 2011;93:18-31 pubmed publisher
    Myristoylation corresponds to the irreversible covalent linkage of the 14-carbon saturated fatty acid, myristic acid, to the N-terminal glycine of many eukaryotic and viral proteins. It is catalyzed by N-myristoyltransferase...
  30. Utsumi T, Sakurai N, Nakano K, Ishisaka R. C-terminal 15 kDa fragment of cytoskeletal actin is posttranslationally N-myristoylated upon caspase-mediated cleavage and targeted to mitochondria. FEBS Lett. 2003;539:37-44 pubmed
    ..of known caspase substrates to protein N-myristoylation was evaluated by in vivo metabolic labeling with [(3)H]myristic acid in transfected cells using a fusion protein in which the query sequence was fused to a model protein...
  31. Ra ces M, Gargantini P, Chinchilla D, Crespi M, T llez I n M, Ulloa R. Regulation of CDPK isoforms during tuber development. Plant Mol Biol. 2003;52:1011-24 pubmed
    ..Altogether, our data suggest that sequential activation of StCDPK3 and StCDPK1 and the subcellular localisation of StCDPK1 might be critical regulatory steps of calcium signalling during potato tuber development...
  32. Gaffarogullari E, Masterson L, Metcalfe E, Traaseth N, Balatri E, Musa M, et al. A myristoyl/phosphoserine switch controls cAMP-dependent protein kinase association to membranes. J Mol Biol. 2011;411:823-36 pubmed publisher
  33. Gonzalez E, Kou R, Lin A, Golan D, Michel T. Subcellular targeting and agonist-induced site-specific phosphorylation of endothelial nitric-oxide synthase. J Biol Chem. 2002;277:39554-60 pubmed
  34. Konno D, Ko J, Usui S, Hori K, Maruoka H, Inui M, et al. The postsynaptic density and dendritic raft localization of PSD-Zip70, which contains an N-myristoylation sequence and leucine-zipper motifs. J Cell Sci. 2002;115:4695-706 pubmed
    ..These results suggest that PSD-Zip70 may be involved in the dynamic properties of the structure and function of the postsynaptic site. ..
  35. Weiergräber O, Senin I, Philippov P, Granzin J, Koch K. Impact of N-terminal myristoylation on the Ca2+-dependent conformational transition in recoverin. J Biol Chem. 2003;278:22972-9 pubmed
    ..e. the T conformation) during the stepwise transition toward the fully Ca2+-occupied state. On the basis of these observations, a refined model for the role of the myristoyl group as an intrinsic allosteric modulator is proposed. ..
  36. Utsumi T, Ohta H, Kayano Y, Sakurai N, Ozoe Y. The N-terminus of B96Bom, a Bombyx mori G-protein-coupled receptor, is N-myristoylated and translocated across the membrane. FEBS J. 2005;272:472-81 pubmed
    ..To our knowledge, this is the first report showing that a eukaryotic transmembrane protein can be N-myristoylated and that the N-myristoylated N-terminus of the protein can be translocated across the membrane. ..
  37. Ames J, Hamasaki N, Molchanova T. Structure and calcium-binding studies of a recoverin mutant (E85Q) in an allosteric intermediate state. Biochemistry. 2002;41:5776-87 pubmed
    ..We propose that Ca2+-bound myr-E85Q may represent a stable intermediate state in the kinetic mechanism of the calcium-myristoyl switch. ..
  38. Farazi T, Waksman G, Gordon J. The biology and enzymology of protein N-myristoylation. J Biol Chem. 2001;276:39501-4 pubmed
  39. Robbins S, Quintrell N, Bishop J. Myristoylation and differential palmitoylation of the HCK protein-tyrosine kinases govern their attachment to membranes and association with caveolae. Mol Cell Biol. 1995;15:3507-15 pubmed
    ..Taken together, the results suggest that HCK and several of its relatives may participate in the functions of caveolae, which apparently include the transduction of signals across the plasma membrane to the interior of the cell. ..
  40. Hermida Matsumoto L, Resh M. Human immunodeficiency virus type 1 protease triggers a myristoyl switch that modulates membrane binding of Pr55(gag) and p17MA. J Virol. 1999;73:1902-8 pubmed
    ..We present a model proposing that the HIV-1 protease is the "trigger" for a myristoyl switch mechanism that modulates the membrane associations of Pr55(gag) and p17MA in virions and membranes. ..
  41. Parenti M, Vigano M, Newman C, Milligan G, Magee A. A novel N-terminal motif for palmitoylation of G-protein alpha subunits. Biochem J. 1993;291 ( Pt 2):349-53 pubmed
    ..The non-palmitoylated alpha o mutant is still myristoylated but shows reduced membrane binding, suggesting that reversible palmitoylation may regulate G alpha localization and function. ..
  42. Stevenson F, Bursten S, Locksley R, Lovett D. Myristyl acylation of the tumor necrosis factor alpha precursor on specific lysine residues. J Exp Med. 1992;176:1053-62 pubmed
    ..Specific myristyl acylation of the TNF propiece may facilitate membrane insertion or anchoring of this critical inflammatory mediator. ..
  43. Zha J, Weiler S, Oh K, Wei M, Korsmeyer S. Posttranslational N-myristoylation of BID as a molecular switch for targeting mitochondria and apoptosis. Science. 2000;290:1761-5 pubmed
    ..This post-proteolytic N-myristoylation serves as an activating switch, enhancing BID-induced release of cytochrome c and cell death. ..
  44. Burgoyne R, Weiss J. The neuronal calcium sensor family of Ca2+-binding proteins. Biochem J. 2001;353:1-12 pubmed
    ..In the present review we describe the known sequences and structures of the NCS proteins, information on their interactions with target proteins and current knowledge about their cellular and physiological functions. ..
  45. Liu J, Sessa W. Identification of covalently bound amino-terminal myristic acid in endothelial nitric oxide synthase. J Biol Chem. 1994;269:11691-4 pubmed
    ..Although eNOS was metabolically labeled with [3H]myristic acid and mutation of glycine 2 in the N-myristoylation consensus sequence changed the particulate localization of ..
  46. Ozols J, Carr S, Strittmatter P. Identification of the NH2-terminal blocking group of NADH-cytochrome b5 reductase as myristic acid and the complete amino acid sequence of the membrane-binding domain. J Biol Chem. 1984;259:13349-54 pubmed
    ..chemical ionization mass spectroscopy of the underivatized NH2-terminal tetrapeptide confirmed the presence of myristic acid, identified its linkage to the NH2 terminus and established CH3(CH2)12-CO-Gly-Ala-Gln-Leu as the NH2-terminal ..
  47. Goldberg J. Structural basis for activation of ARF GTPase: mechanisms of guanine nucleotide exchange and GTP-myristoyl switching. Cell. 1998;95:237-48 pubmed
    ..The transition controls the exposure of the myristoylated N terminus, explaining how ARF GTPases couple the GDP-GTP conformational switch to membrane binding. ..
  48. Curry S, Mandelkow H, Brick P, Franks N. Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites. Nat Struct Biol. 1998;5:827-35 pubmed
    ..These pockets are distributed asymmetrically throughout the HSA molecule, despite its symmetrical repeating domain structure. ..
  49. Resh M. Fatty acylation of proteins: new insights into membrane targeting of myristoylated and palmitoylated proteins. Biochim Biophys Acta. 1999;1451:1-16 pubmed
    ..The use of myristoyl switches and regulated depalmitoylation as mechanisms for achieving reversible membrane binding and regulated signaling will also be explored. ..
  50. Maurer Stroh S, Eisenhaber B, Eisenhaber F. N-terminal N-myristoylation of proteins: refinement of the sequence motif and its taxon-specific differences. J Mol Biol. 2002;317:523-40 pubmed
    ..An exhaustive search for NMT-homologues led to the discovery of two putative entomopoxviral NMTs. ..
  51. Desmeules P, Grandbois M, Bondarenko V, Yamazaki A, Salesse C. Measurement of membrane binding between recoverin, a calcium-myristoyl switch protein, and lipid bilayers by AFM-based force spectroscopy. Biophys J. 2002;82:3343-50 pubmed
    ..However, no binding was observed in the absence of Ca(2+). Experiments with nonmyristoylated recoverin confirmed these observations. Our results are consistent with previously measured extraction forces of lipids from membranes. ..
  52. Wang J, Kiyokawa E, Verdin E, Trono D. The Nef protein of HIV-1 associates with rafts and primes T cells for activation. Proc Natl Acad Sci U S A. 2000;97:394-9 pubmed
    ..Overall, these data suggest that Nef acts at the level of rafts to prime T cells for activation. Likely consequences of this effect are the promotion of HIV-1 replication and the facilitation of virus spread. ..