ChemInform Abstract: Protease-Catalyzed Regioselective Esterification of Sugars and Related Compounds in Anhydrous Dimethylformamide.

ChemInform Abstract

The proteolytic enzyme subtilisin is very active as a catalyst for the selective acylation of carbohydrates and other sugar-containing compounds. For example, the sugars (Ia) (glucose), (Ib) (maltose), (Ic) (cellobiose), (Id) (sucrose), and (Ie) (maltotriose) can be selectively converted to the monobutyryl esters (II) in a transesterification reaction using the ester (III). Similarly, the main product (IVb) is obtained from lactose (IVa). The reaction can be extended to an effective preparative esterification of natural compounds such as salicin (Va) (→ (Vb)) as well as riboflavin, adenosine, or uridine. In addition to the butyryl group, various N-acetylamino acid residues are enzymatically introduced into sugars.