monoacyl

Monoacyl denotes a molecule bearing exactly one acyl group, typically an acyl substituent derived from a carboxylic acid (R–CO–). The term is widely used in lipid chemistry to describe monoacyl derivatives of various backbones, most commonly monoacylglycerols (MAGs).

Monoacylglycerols consist of glycerol with a single fatty acid esterified to one hydroxyl group, yielding 1- MAG or 2-MAG depending on the site of acylation. In mammalian digestion, triglycerides are hydrolyzed by pancreatic lipase to produce free fatty acids and MAGs, with 2-MAG often the predominant product; MAGs are absorbed by enterocytes and re-esterified into triglycerides for transport as lipoproteins.

The monoacyl designation is also applied to other substrates that carry a single acyl group, such as monoacylated amines or peptides, where one fatty acyl chain is attached via an amide or ester linkage. The concept emphasizes the presence of a single acyl unit rather than multiple acyl substituents.

Synthesis typically involves selective monoesterification or monoacylation of a substrate, a challenge due to multiple reactive sites; chemical approaches often employ protecting groups, while enzymatic methods using lipases or acyltransferases can furnish MAGs with regioselectivity under mild conditions.

In nutrition and food science, MAGs contribute to fat digestion, emulsification, and flavor delivery, and some MAGs have signaling roles in lipid metabolism. The related terms diacyl and triacyl refer to substrates bearing two or three acyl groups, respectively.