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Acylation

Lianyungang Klinechem Co.,Ltd | Updated: Nov 28, 2018

In chemistryacylation (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 catalystsacyl 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:

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The mechanism of this reaction is electrophilic aromatic substitution.

Acyl halides and anhydrides of carboxylic acids are also commonly used acylating agents. In some cases, active esters exhibit comparable reactivity. All react with amines to form amides and alcohols to form esters by nucleophilic acyl substitution.

Acylation can be used to prevent rearrangement reactions that would normally occur in alkylation. To do this an acylation reaction is performed, then the carbonyl is removed by Clemmensen reduction or a similar process. [1]

Acylation in biology

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).[2] Protein acylation has been observed as a mechanism of biological signaling.[3]

See also

·         Acetyl

·         Ketene

References

1.     Jump up^ Vollhardt, Peter; Schore, Neil (2014). Organic Chemistry: Structure and Function (7th ed.). New York, NY: W.H. Freeman and Company. pp. 714–715. ISBN 978-1-4641-2027-5.

2.     Jump up^ 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)00075-0PMID 10446384.

3.     Jump up^ 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.


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