reacylationthe

Reacylation is the chemical process of reintroducing or transferring an acyl group to a molecule, often after some prior loss or modification of an acyl group. In organic synthesis, reacylation refers to restoring an acylated functionality by reacting a nucleophile such as a amine, alcohol, or thiol with an activated acyl donor. Common acyl donors include acid chlorides, acid anhydrides, and activated esters; catalysts or bases facilitate the reaction, and choice of donor and solvent influences selectivity and yield. Reacylation is a key step in many protective-group strategies, where a temporarily deprotected amine or alcohol is re-acylated to return the molecule to its original protected form or to advance toward the target compound.

In biochemistry, reacylation is prominently discussed in the context of lipid remodeling. The Lands cycle describes how phospholipids can be deacylated by phospholipase A2 to form lysophospholipids and free fatty acids, followed by reacylation with fatty acyl-CoA by acyltransferases to regenerate phospholipids. This reacylation step is essential for adjusting membrane composition and fluidity in response to cellular conditions.

In protein chemistry, acylation reactions confer lipid-like or other acyl groups to proteins, though the term reacylation is less common; when used, it generally refers to the restoration of an acylated state after a reversible modification or deacylation event.

Overall, reacylation plays a broad role across organic synthesis and biology, enabling the reformation of acylated products and contributing to membrane dynamics and material properties.