Biocatalytic <i>N</i>‐Acylation of Amines in Water Using an Acyltransferase from <i>Mycobacterium smegmatis</i>

Abstract

Abstract A straightforward one‐step biocatalyzed synthesis of different N ‐acyl amides in water was accomplished using the versatile and chemoselective acyltransferase from Mycobacterium smegmatis (MsAcT). Acetylation of primary arylalkyl amines was achieved with a range of acetyl donors in biphasic systems within 1 hour and at room temperature. Vinyl acetate was the best donor which could be employed in the N ‐acetylation of a large range of primary amines in excellent yields (85–99%) after just 20 minutes. Other acyl donors (including formyl‐, propionyl‐, and butyryl‐donors) were also efficiently employed in the biocatalytic N ‐acylation. Finally, the biocatalyst was tested in transamidation reactions using acetamide as acetyl donor in aqueous medium, reaching yields of 60–70%. This work expands the toolbox of preparative methods for the formation of N ‐acyl amides, describing a biocatalytic approach easy to accomplish under mild conditions in water. magnified image