Mechanism of Acyl Group Migration in Carbohydrates

Acyl group migration has been the subject of several studies. Such migration processes may cause problems during synthesis, isolation, and purification of different acyl-bearing compounds, and have biological relevance, for example, in the metabolism of pharmaceuticals. Considering the recent evidence of acyl group migration being possible even over glycosidic bonds, it could be hypothesized to be involved also in the regulation of biological activity of natural polysaccharides in the host cells. Migrations are mostly observed in carbohydrates, typically having several hydroxyl groups near each other. Several studies have investigated the migration in a single or only a few different carbohydrate molecules, providing different suggestions for the mechanisms of migration, seldom supported by comprehensive computational investigations. In this concept article we discuss the recent progress on the mechanistic aspects of acyl group migration, with carbohydrates in particular focus.