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

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

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.

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, 360(24), 4814-4819. https://doi.org/10.1002/adsc.201801061

• Journal Article Type: Article
• Acceptance Date: Oct 5, 2018
• Online Publication Date: Oct 7, 2018
• Publication Date: Oct 7, 2018
• Deposit Date: Oct 19, 2018
• Publicly Available Date: Oct 8, 2019
• Journal: Advanced Synthesis & Catalysis
• Print ISSN: 1615-4150
• Electronic ISSN: 1615-4169
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 360
• Issue: 24
• Pages: 4814-4819
• DOI: https://doi.org/10.1002/adsc.201801061
• Keywords: Amide synthesis; Biocatalysis; Transamidation; Acyltransferase; Mycobacterium smegmatis
• Public URL: https://nottingham-repository.worktribe.com/output/1176587
• 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
• Contract Date: Oct 19, 2018