Biocatalytic N‐Acylation of Amines in Water Using an Acyltransferase from Mycobacterium smegmatis,Advanced Synthesis & Catalysis

当前位置： X-MOL 学术 › Adv. Synth. Catal. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Biocatalytic N‐Acylation of Amines in Water Using an Acyltransferase from Mycobacterium smegmatis
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-10-30 , DOI: 10.1002/adsc.201801061
Martina Letizia Contente ₁ , Andrea Pinto ₂ , Francesco Molinari ₂ , Francesca Paradisi ₁

Affiliation

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.

中文翻译：

使用耻垢分枝杆菌的酰基转移酶对水中的胺进行生物催化N酰化

使用耻垢分枝杆菌（MsAcT）的多功能和化学选择性酰基转移酶可直接在水中进行简单的一步式生物催化合成各种N酰基酰胺。在1小时内和室温下，在双相体系中使用一系列乙酰基供体实现了芳基伯烷基伯胺的乙酰化。醋酸乙烯酯是最好的供体，仅需20分钟，它就可以以优异的收率（85-99％）用于各种伯胺的N-乙酰化。其他酰基供体（包括甲酰基，丙酰基和丁酰基供体）也被有效地用于生物催化氮中。酰化。最后，在乙酰胺作为水介质中的乙酰基供体的转酰胺化反应中对生物催化剂进行了测试，收率达到60-70％。这项工作扩展了用于形成N酰基酰胺的制备方法的工具箱，描述了在温和条件下易于在水中完成的生物催化方法。

更新日期：2018-10-30

点击分享查看原文

点击收藏

公开下载

阅读更多本刊最新论文本刊介绍/投稿指南11