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22-AUGUST-2008 06:13:22 - Acetylation Salicylic acid is acetylated to form asprin Salicylic acid is acetylated to form asprin Acetylation or in IUPAC nomenclature ethanoylation describes a reaction that introduces an acetyl functional group into an organic compound. Deacetylation is the removal of the acetyl group. Moreover, it is that process of introducing an acetyl group resulting in an acetoxy group into a compound, specifically, the substitution of an acetyl group for an active hydrogen atom. A reaction involving the replacement of the hydrogen atom of a hydroxyl group with an acetyl group CH3 CO yields a specific ester, the acetate. Acetic anhydride is commonly used as an acetylating agent reacting with free hydroxyl groups. For example, it is used in the synthesis of Aspirin. Contents 1 Acetylation of proteins 1.1 N-alpha-terminal Acetylation 1.2 Histone Acetylation and Deacetylation 1.3 Tubulin Acetylation and Deacetylation 2 See also Acetylation of proteins In biology, i.e. in living cells, acetylation occurs as a co-translational and post-translational modification of proteins, for example, histones, p53, and tubulins. N-alpha-terminal Acetylation Acetylation of the N-terminal alpha-amine of proteins is a widespread modification in eukaryotes. 40-50% of yeast proteins, and 80-90% of human proteins are modified in this manner, and the pattern of modification is found to be conserved throughout evolution. The modification is performed by N-alpha-acetyltransferases NATs, a sub-family of the GNAT superfamily of acetyltransferases, which also include histone acetyl transferases. The GNATs transfer the acetylgroup from acetyl-coenzyme A to the amine group. The NATs have been most extensively studied in yeast. Here three NAT complexes, NatA/B/C, have been found to perform most N-alpha-terminal acetylations. They have sequence specificity for their substrates, and it is believed that they are associated with the ribosome, where they acetylate nascent polypeptides co-translationally. In humans, only one NAT complex , the human NatA, has been identified and characterized. Subunits of the human NatA complex have been coupled to cancer-related processes such as hypoxia-response and the beta-catenin pathway. It has been found to be over-expressed in papillary thyroid carcinoma and neuroblastoma. Despite being such a conserved and widespread modification, little is known about the biological role of N-alpha-terminal acetylation. Proteins such as actin and tropomyosin have been found to be dependent of NatB acetylation to form proper actin filaments. This is yet only an example of the potential importance of this modification. Histone Acetylation and Deacetylation In histone acetylation and deacetylation, the histones are acetylated and deacetylated on lysine residues in the N-terminal tail as part of gene regulation. Typically, these reactions are catalyzed by enzymes with histone acetyltransferase HAt or histone deacetylase HDAc activity. Although it should be noted that HATs and HDACs can modify the acetylation status of non-histone proteins as well. Tubulin Acetylation and Deacetylation Tubulin Acetylation and Deacetylation system is well worked out in Chlamydomonas. A Tubulin acetyltransferase located in the axoneme acetylates a specific lysine residue in the α-tubulin subunit in assembled microtubule. Once disassembled, this acetylation can be removed by another specific deacetylase which is cytosolic. Thus the axonemal microtubules long half life carry this signature acetylation absent from cytosolic microtubules short half life. See also Acetoxy_group Acylation Organic synthesis v d e Protein primary structure and posttranslational modifications General Protein biosynthesis | Peptide bond | Proteolysis | Racemization | N-O acyl shift N terminus Acetylation | Formylation | Pyroglutamate | Methylation | Glycation | Myristoylation Gly | carbamylation C terminus Amidation | Glycosyl phosphatidylinositol GPI | O-methylation | Glypiation | Ubiquitination | Sumoylation Lysine Methylation | Acetylation | Acylation | Hydroxylation | Ubiquitination | SUMOylation | Desmosine | ADP-ribosylation | Deamination and Oxidation to aldehyde Cysteine Disulfide bond | Prenylation | Palmitoylation Serine/Threonine Phosphorylation | Glycosylation | Methylidene-imidazolone MIO formation Tyrosine Phosphorylation | Sulfation | Porphyrin ring linkage | Flavin linkage | p-Hydroxybenzylidene-imidazolone formation | Lysine tyrosyl quinone LTQ formation | Topaquinone TPQ formation Asparagine Deamidation | Glycosylation Aspartate Succinimide formation Glutamine Transglutamination Glutamate Carboxylation | Methylation | Polyglutamylation | Polyglycylation Arginine Citrullination | Methylation Proline Hydroxylation â†?Amino acids Secondary structure→ Retrieved from http://en..org/wiki/Acetylation Categories: Organic reactions | Proteins | Posttranslational modification Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Français Italiano 日本語 Polski Português SlovenÅ¡Ä?ina Suomi This page was last modified on 3 August 2008, at 22:54
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