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用于高效对映选择性构建手性2-恶唑烷酮的酶催化C(sp)-H胺化反应

Enzyme-catalyzed C(sp)-H aminations for the highly enantioselective construction of chiral 2-oxazolidinones.

作者信息

Gao Hanzi, Li Miao, Zheng Guojun

机构信息

State Key Laboratory of Chemical Resources Engineering, Beijing University of Chemical Technology Beijing 100029 People's Republic of China

出版信息

RSC Adv. 2025 Jun 10;15(25):19640-19644. doi: 10.1039/d5ra01905b.

Abstract

As a rapidly growing field, C(sp)-H functionalization is being used to access a wide range of important molecular targets. The enzymatic activity of C(sp)-H is a powerful synthetic tool to develop valuable building blocks. In this study, engineered myoglobin variants were found to be capable of C(sp)-H activation under mild conditions mediated nitrene transfer. Using this approach, 2-oxazolidinones and γ-lactams with high enantioselectivity were obtained through intramolecular cyclization using readily available and stable -acetoxyamides as substrates.

摘要

作为一个快速发展的领域,C(sp)−H官能团化正被用于合成各种重要的分子目标。C(sp)−H的酶促活性是开发有价值的结构单元的强大合成工具。在本研究中,发现工程改造的肌红蛋白变体能够在温和条件下介导的氮宾转移反应中实现C(sp)−H活化。利用这种方法,以易于获得且稳定的N−乙酰氧基酰胺为底物,通过分子内环化反应,以高对映选择性得到了2-恶唑烷酮和γ-内酰胺。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a172/12151034/f43c1fa06123/d5ra01905b-s1.jpg

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