Biocatalytic N‐Acylation of Amines in Water Using an Acyltransferase from Mycobacterium smegmatis. Issue 24 (30th October 2018)

• Record Type: Journal Article
• Authors: Contente, Martina Letizia; Pinto, Andrea; Molinari, Francesco; Paradisi, Francesca
• Is Part Of: Advanced synthesis & catalysis. Volume 360:Issue 24(2018)
• Page Start: 4814
• Page End: 4819
• Publication Date: 2018-10-30
• Subjects: Amide synthesis -- Biocatalysis -- Transamidation -- Acyltransferase -- Mycobacterium smegmatis; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201801061
• Languages: English
• ISSNs: 1615-4150

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. Abstract :