Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 24, Pages 4814-4819Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201801061
Keywords
Amide synthesis; Biocatalysis; Transamidation; Acyltransferase; Mycobacterium smegmatis
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Funding
- European Union [792804_AROMAs-FLOW]
- Piano di Sostegno alla Ricerca 2015/2017-Linea 2_Azione A of the University of Milan
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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.
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