Cacetylation

Cacetylation is not a widely standardized term in chemistry. In many contexts it may refer to acetylation that occurs at a carbon center (often called C-acetylation) rather than at heteroatoms, or it may simply be a misnomer for acetylation in general. Acetylation, more broadly, is the installation of an acetyl group (CH3CO−) onto a substrate.

In organic synthesis, acetylation most commonly targets nitrogen, oxygen, or sulfur atoms, producing N-acetyl, O-acetyl, or S-acetyl derivatives. Reagents such as acetyl chloride, acetic anhydride, or acetyl donors like acetyl-CoA in biological contexts are typically used. The outcome is influenced by the substrate, solvent, and catalyst or enzyme involved. Carbon-centered acetylation, or C-acetylation, is comparatively less common and often more challenging. It may proceed via enolate or other carbon-centered nucleophiles reacting with acetylating agents, or through transition-metal- or radical-mediated pathways that enable carbon–carbon bond formation with an acetyl fragment. Such processes are active areas of research in modern organic catalysis and may require specialized catalysts and controlled conditions.

Biological relevance centers on acetylation as a post-translational modification. N-terminal acetylation and N- or O-acetylation of amino acid residues influence protein stability and function, with acetyl-CoA serving as a key acetyl donor in cells. Histone acetylation modulates chromatin structure and gene expression, playing a major role in regulation of transcription and cellular processes.

Analytical aspects include common characterization by mass spectrometry and NMR, along with careful control of reagents due to the reactive and sometimes corrosive nature of acetylating agents.