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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
MeSH Review


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Disease relevance of Acylation


High impact information on Acylation

  • The AGPAT2 enzyme catalyzes the acylation of lysophosphatidic acid to form phosphatidic acid, a key intermediate in the biosynthesis of triacylglycerol and glycerophospholipids [5].
  • Mutations in SUPH-STE16 prevent the membrane localization and maturation of RAS protein, as well as the fatty acid acylation of it and other membrane proteins [6].
  • These amide aminoacyl-tRNAs can be formed by the direct acylation of tRNA, catalysed by asparaginyl-tRNA synthetase and glutaminyl-tRNA synthetase, respectively [7].
  • In addition, we show that exposure to nitric oxide inhibits thioester-linked long-chain fatty acylation of neuronal proteins, possibly through a direct modification of substrate cysteine thiols [8].
  • Surprisingly, this partition of aaRS in two classes is found to be strongly correlated on the functional level with the acylation occurring either on the 2' OH (class I) or 3' OH (class II) of the ribose of the last nucleotide of tRNA [9].

Chemical compound and disease context of Acylation


Biological context of Acylation

  • Here we propose two possible mechanisms for LPS recognition and signalling that take into account both the structural information available for TLR4 and MD-2, and the determinants of endotoxicity, namely, the acylation and phosphorylation patterns of LPS [15].
  • We show here that ongoing fatty acylation can be inhibited selectively by long-chain homologues of the antibiotic tunicamycin, a known inhibitor of N-linked glycosylation [16].
  • The endosomal localization of Ara6 requires N-terminal fatty acylation, nucleotide binding and the C-terminal amino acid sequence coordinately [17].
  • We show that TIP1 binds the acyl group palmitate, that it can rescue the morphological, temperature sensitivity, and yeast casein kinase2 localization defects of the yeast S-acyl transferase mutant akr1Delta, and that inhibition of acylation in wild-type Arabidopsis roots reproduces the Tip1- mutant phenotype [18].
  • In hyperapoB cells, BP II markedly increased (up to 9-fold) the incorporation of [14C]oleate into cholesteryl ester compared with that in normal cells; in addition, there was a 50% decrease in the stimulation of triglyceride acylation and cholesterol esterification with BP I [19].

Anatomical context of Acylation

  • Radioimmunoprecipitates from the supernates of labeled monocytes indicated that the processed or mature 17-kD form of TNF does not contain myristate, suggesting that the site of acylation occurs within the 76-amino acid propiece of the precursor molecule [20].
  • These results suggest a novel role for fatty acylation in the specific compartmentalization of eNOS and most likely, for other dually acylated proteins, to the Golgi complex [21].
  • Both GlcN-(2-O-octyl)PI and GlcNAc(2-O-octyl)PI also inhibit inositol acylation of Man(1-3)GlcN-PI and, consequently, the addition of the ethanolamine phosphate bridge in the T.brucei cell-free system [22].
  • Two different methods, stimulation of transport by fatty acyl-coenzyme A (CoA) and inhibition of transport by a nonhydrolyzable analogue of palmitoyl-CoA, reveal that fatty acylation is required to promote fusion of transport vesicles with Golgi cisternae [23].
  • Moreover, they demonstrate that inositol acylation is required for mannosylation in the HeLa cell GPI biosynthetic pathway, whereas it is required for ethanolamine phosphate addition in the T.brucei GPI biosynthetic pathway [24].

Associations of Acylation with chemical compounds

  • Acylation of proteins with myristic acid occurs cotranslationally [25].
  • Amino acid acylation: a mechanism of nitrogen excretion in inborn errors of urea synthesis [26].
  • Treatment of a patient deficient in carbamyl phosphate synthetase with benzoate or phenylacetic acid resulted in an increase in urinary nitrogen, which could be accounted for by the respective amino acid acylation product, hippurate or phenylacetylgultamine [26].
  • A synthetic palmitoylated peptide corresponding to the tryptic fragment (glutamine 972 to arginine 984) that contained the acylation blocked AC toxin-induced accumulation of adenosine 3',5'-monophosphate, whereas the non-acylated peptide had no effect [27].
  • Acylation of the purified erythromycin-producing polyketide synthase has shown that all six acyltransferase domains have identical stereospecificity for their normal substrate, (2S)-methylmalonyl-CoA [28].

Gene context of Acylation

  • Acylation of the IL-1 alpha precursor by a previously unrecognized lysyl epsilon-amino N-myristoyl-transferase activity may facilitate its specific membrane targeting [29].
  • For the alpha 2AAR (human alpha 2 C10) palmitoylation occurs at Cys-442, but it is not known what function such fatty acid acylation subserves [30].
  • The DPR1 product has been shown to be responsible for processing and fatty acid acylation of a-factor and RAS proteins at their carboxyl termini [31].
  • We examined the role of fatty acylation in the maturation of yeast RAS2 protein by creating mutants in the putative palmitate addition site located at the carboxyl terminus of the protein [32].
  • Reversible acylation of eNOS is thought to contribute to the intracellular trafficking of the enzyme; however, protein factor(s) that govern the translocation of the enzyme are still unknown [33].

Analytical, diagnostic and therapeutic context of Acylation


  1. Activation of Escherichia coli prohaemolysin to the mature toxin by acyl carrier protein-dependent fatty acylation. Issartel, J.P., Koronakis, V., Hughes, C. Nature (1991) [Pubmed]
  2. Bacterial nodulation protein NodZ is a chitin oligosaccharide fucosyltransferase which can also recognize related substrates of animal origin. Quinto, C., Wijfjes, A.H., Bloemberg, G.V., Blok-Tip, L., López-Lara, I.M., Lugtenberg, B.J., Thomas-Oates, J.E., Spaink, H.P. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  3. Membrane interactions of simian virus 40 large T-antigen: influence of protein sequences and fatty acid acylation. Klockmann, U., Staufenbiel, M., Deppert, W. Mol. Cell. Biol. (1984) [Pubmed]
  4. Studies on some lipogenic enzymes of cultured myeloid leukemic cells. Okuma, M., Ichikawa, Y., Yamashita, S., Kitajima, K., Numa, S. Blood (1976) [Pubmed]
  5. AGPAT2 is mutated in congenital generalized lipodystrophy linked to chromosome 9q34. Agarwal, A.K., Arioglu, E., De Almeida, S., Akkoc, N., Taylor, S.I., Bowcock, A.M., Barnes, R.I., Garg, A. Nat. Genet. (2002) [Pubmed]
  6. RAM, a gene of yeast required for a functional modification of RAS proteins and for production of mating pheromone a-factor. Powers, S., Michaelis, S., Broek, D., Santa Anna, S., Field, J., Herskowitz, I., Wigler, M. Cell (1986) [Pubmed]
  7. Domain-specific recruitment of amide amino acids for protein synthesis. Tumbula, D.L., Becker, H.D., Chang, W.Z., Söll, D. Nature (2000) [Pubmed]
  8. Neuronal growth cone collapse and inhibition of protein fatty acylation by nitric oxide. Hess, D.T., Patterson, S.I., Smith, D.S., Skene, J.H. Nature (1993) [Pubmed]
  9. Partition of tRNA synthetases into two classes based on mutually exclusive sets of sequence motifs. Eriani, G., Delarue, M., Poch, O., Gangloff, J., Moras, D. Nature (1990) [Pubmed]
  10. Localization of fluorine-18-labeled Mel-14 monoclonal antibody F(ab')2 fragment in a subcutaneous xenograft model. Garg, P.K., Garg, S., Bigner, D.D., Zalutsky, M.R. Cancer Res. (1992) [Pubmed]
  11. Chemical fatty acylation confers hemolytic and toxic activities to adenylate cyclase protoxin of Bordetella pertussis. Heveker, N., Bonnaffé, D., Ullmann, A. J. Biol. Chem. (1994) [Pubmed]
  12. Role of fatty acid acylation of membrane glycoproteins. Absence of palmitic acid in glycoproteins of two serotypes of vesicular stomatitis virus. Kotwal, G.J., Ghosh, H.P. J. Biol. Chem. (1984) [Pubmed]
  13. Cell-free fatty acylation of microsomal integrated and detergent-solubilized glycoprotein of vesicular stomatitis virus. Mack, D., Berger, M., Schmidt, M.F., Kruppa, J. J. Biol. Chem. (1987) [Pubmed]
  14. Cerulenin blocks fatty acid acylation of glycoproteins and inhibits vesicular stomatitis and Sindbis virus particle formation. Schlesinger, M.J., Malfer, C. J. Biol. Chem. (1982) [Pubmed]
  15. MD-2: the Toll 'gatekeeper' in endotoxin signalling. Gangloff, M., Gay, N.J. Trends Biochem. Sci. (2004) [Pubmed]
  16. Novel inhibitory action of tunicamycin homologues suggests a role for dynamic protein fatty acylation in growth cone-mediated neurite extension. Patterson, S.I., Skene, J.H. J. Cell Biol. (1994) [Pubmed]
  17. Ara6, a plant-unique novel type Rab GTPase, functions in the endocytic pathway of Arabidopsis thaliana. Ueda, T., Yamaguchi, M., Uchimiya, H., Nakano, A. EMBO J. (2001) [Pubmed]
  18. The TIP GROWTH DEFECTIVE1 S-acyl transferase regulates plant cell growth in Arabidopsis. Hemsley, P.A., Kemp, A.C., Grierson, C.S. Plant Cell (2005) [Pubmed]
  19. Acylation-stimulatory activity in hyperapobetalipoproteinemic fibroblasts: enhanced cholesterol esterification with another serum basic protein, BP II. Kwiterovich, P., Motevalli, M., Miller, M. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  20. Myristyl acylation of the tumor necrosis factor alpha precursor on specific lysine residues. Stevenson, F.T., Bursten, S.L., Locksley, R.M., Lovett, D.H. J. Exp. Med. (1992) [Pubmed]
  21. The first 35 amino acids and fatty acylation sites determine the molecular targeting of endothelial nitric oxide synthase into the Golgi region of cells: a green fluorescent protein study. Liu, J., Hughes, T.E., Sessa, W.C. J. Cell Biol. (1997) [Pubmed]
  22. Selective inhibitors of the glycosylphosphatidylinositol biosynthetic pathway of Trypanosoma brucei. Smith, T.K., Sharma, D.K., Crossman, A., Brimacombe, J.S., Ferguson, M.A. EMBO J. (1999) [Pubmed]
  23. Fatty acylation promotes fusion of transport vesicles with Golgi cisternae. Pfanner, N., Glick, B.S., Arden, S.R., Rothman, J.E. J. Cell Biol. (1990) [Pubmed]
  24. Parasite and mammalian GPI biosynthetic pathways can be distinguished using synthetic substrate analogues. Smith, T.K., Sharma, D.K., Crossman, A., Dix, A., Brimacombe, J.S., Ferguson, M.A. EMBO J. (1997) [Pubmed]
  25. Acylation of proteins with myristic acid occurs cotranslationally. Wilcox, C., Hu, J.S., Olson, E.N. Science (1987) [Pubmed]
  26. Amino acid acylation: a mechanism of nitrogen excretion in inborn errors of urea synthesis. Brusilow, S., Tinker, J., Batshaw, M.L. Science (1980) [Pubmed]
  27. Internal lysine palmitoylation in adenylate cyclase toxin from Bordetella pertussis. Hackett, M., Guo, L., Shabanowitz, J., Hunt, D.F., Hewlett, E.L. Science (1994) [Pubmed]
  28. Stereospecific acyl transfers on the erythromycin-producing polyketide synthase. Marsden, A.F., Caffrey, P., Aparicio, J.F., Loughran, M.S., Staunton, J., Leadlay, P.F. Science (1994) [Pubmed]
  29. 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]
  30. The palmitoylated cysteine of the cytoplasmic tail of alpha 2A-adrenergic receptors confers subtype-specific agonist-promoted downregulation. Eason, M.G., Jacinto, M.T., Theiss, C.T., Liggett, S.B. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  31. Role of SGP2, a suppressor of a gpa1 mutation, in the mating-factor signaling pathway of Saccharomyces cerevisiae. Nakayama, N., Arai, K., Matsumoto, K. Mol. Cell. Biol. (1988) [Pubmed]
  32. Fatty acylation is important but not essential for Saccharomyces cerevisiae RAS function. Deschenes, R.J., Broach, J.R. Mol. Cell. Biol. (1987) [Pubmed]
  33. NOSIP, a novel modulator of endothelial nitric oxide synthase activity. Dedio, J., König, P., Wohlfart, P., Schroeder, C., Kummer, W., Müller-Esterl, W. FASEB J. (2001) [Pubmed]
  34. Adduct detection by acylation with [35S]methionine: analysis of DNA adducts of 4-aminobiphenyl. Sheabar, F.Z., Morningstar, M.L., Wogan, G.N. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  35. The 5-hydroxytryptamine(1A) receptor is stably palmitoylated, and acylation is critical for communication of receptor with Gi protein. Papoucheva, E., Dumuis, A., Sebben, M., Richter, D.W., Ponimaskin, E.G. J. Biol. Chem. (2004) [Pubmed]
  36. Metabolism of platelet-activating factor in human platelets. Transacylase-mediated synthesis of 1-O-alkyl-2-arachidonoyl-sn-glycero-3-phosphocholine. Kramer, R.M., Patton, G.M., Pritzker, C.R., Deykin, D. J. Biol. Chem. (1984) [Pubmed]
  37. Preparation of an ecdysone immunogen for radioimmunoassay work. Hung, D.T., Benner, S.A., Williams, C.M. J. Biol. Chem. (1980) [Pubmed]
  38. Acylation of endogenous myelin proteolipid protein with different acyl-CoAs. Bizzozero, O.A., McGarry, J.F., Lees, M.B. J. Biol. Chem. (1987) [Pubmed]
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