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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.

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

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