Acylation

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In chemistry, acylation (rarely, but more formally: alkanoylation) is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent.

Because they form a strong electrophile when treated with some metal catalysts, acyl halides are commonly used as acylating agents. For example, Friedel-Crafts acylation uses acetyl chloride (ethanoyl chloride), CH3COCl, as the agent and aluminum chloride (AlCl3) as a catalyst to add an ethanoyl (acetyl) group to benzene:

Friedel-Crafts acylation of benzene by ethanoyl chloride

The mechanism of this reaction is electrophilic substitution.

Acyl halides and anhydrides of carboxylic acids are also commonly used acylating agents to acylate amines to form amides or acylate alcohols to form esters. The amines and alcohols are nucleophiles; the mechanism is nucleophilic addition-elimination. Succinic acid is also commonly used in a specific type of acylation called succination. Oversuccination occurs when more than one succinate adds to a single compound.

Acylation in biology[edit]

Protein acylation is the post-translational modification of proteins via the attachment of functional groups through acyl linkages. One prominent type is fatty acylation, the addition of fatty acids to particular amino acids (e.g. myristoylation or palmitoylation).[1] Protein acylation has been observed as a mechanism of biological signaling.[2]

See also[edit]

References[edit]

  1. ^ Resh, M. D. (1999). "Fatty acylation of proteins: New insights into membrane targeting of myristoylated and palmitoylated proteins". Biochimica et Biophysica Acta 1451 (1): 1–16. doi:10.1016/S0167-4889(99)00075-0. PMID 10446384.  edit
  2. ^ Towler, D A; Gordon, J I; Adams, S P; Glaser, L (1988). "The Biology and Enzymology of Eukaryotic Protein Acylation". Annual Review of Biochemistry 57 (1): 69–97. doi:10.1146/annurev.bi.57.070188.000441.  edit