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Acylation

German: Acylierung

1 Definition

An acylation is the introduction of an acyl group into a chemical compound and is mostly used in the context of proteins (protein modification).

An important acylation of aromatic compounds is the Friedel-Crafts acylation. [1]

2 Biochemistry

The coupling of fatty acids like myristic acid or palmitic acid leads to the binding of the acylated proteins to the cell membrane. This process can be crucial for the function of the whole protein. [2]

Certain acyltransferases catalyze the process of acylation. For this, they use activated fatty acid-CoA compounds. This involves myristic acid being bound by an amid bridge to an N-terminal glycine and palmitic acid being connected by a thioester bond to cysteine. This cotranslational myristoylation is irreversible and takes place after the N-terminal initiator methionine has been removed. The post-translational palmitoylation, however is reversible, due to its weaker thioester bond. [3]

Acylation, as well as isoprenylation are commonly found in a protein.

3 Clinical relevance

Some forms of colon carcinoma are associated with increased tyrosine kinase Src levels. This enzyme is only active in its myristoylated form. Src is a part of the intracellular signal transduction pathway and among other things increases the expression of a urokinase receptor that absorbs the urokinase protease from the environment which results in a drastically increased urokinase concentration. This situation leads to the proteolytic activation of plasminogen to plasmin and thus causes the degradation of matrix elements and the activation of collagenases. This way an unambiguous correlation with invasiveness and metastasization of the tumor can be determined. [4]

4 References

  1. http://www.spektrum.de/lexikon/chemie/friedel-crafts-reaktionen/3496
  2. "Duale Reihe Biochemie" - Joachim Rassow et. al., Thieme-Verlag, third edition
  3. http://www.spektrum.de/lexikon/biologie/acylierung-von-proteinen/887
  4. "Duale Reihe Biochemie" - Joachim Rassow et. al., Thieme-Verlag, third edition

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