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Biocatalytic N-acylation of amines in water using an acyltransferase from Mycobacterium smegmatis

Contente, Martina; Pinto, Andrea; Molinari, Francesco; Paradisi, Francesca

Authors

Martina Contente

Andrea Pinto

Francesco Molinari

Francesca Paradisi



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.

Journal Article Type Article
Publication Date Oct 7, 2018
Journal Advanced Synthesis & Catalysis
Print ISSN 1615-4150
Electronic ISSN 1615-4169
Publisher Wiley
Peer Reviewed Peer Reviewed
APA6 Citation Contente, M., Pinto, A., Molinari, F., & Paradisi, F. (2018). Biocatalytic N-acylation of amines in water using an acyltransferase from Mycobacterium smegmatis. Advanced Synthesis and Catalysis, doi:10.1002/adsc.201801061. ISSN 1615-4150
DOI https://doi.org/10.1002/adsc.201801061
Keywords Amide synthesis; Biocatalysis; Transamidation; Acyltransferase; Mycobacterium smegmatis
Publisher URL https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201801061
Additional Information This is an Accepted Manuscript of an article published by Taylor & Francis in Advanced Synthesis & Catalysis on 07/10/2018, available online: http://www.tandfonline.com/10.1002/adsc.201801061

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