硝化作用
化学
对映体药物
立体中心
对映选择合成
动力学分辨率
生物催化
化学选择性
有机化学
组合化学
催化作用
反应机理
作者
Huihui Wang,Nan‐Wei Wan,Run-Ping Miao,Cheng-Li He,Yong‐Zheng Chen,Zhi‐Qiang Liu,Yu‐Guo Zheng
标识
DOI:10.1002/anie.202205790
摘要
We report the discovery of an unusual halohydrin dehalogenase, HHDHamb, that can work under relatively low acidic conditions and extremely low temperatures for the bio-nitration of epoxides using nitrite as a nitrating agent. The bio-nitration strategy exhibits high chemo-, regio-, and enantioselectivity, catalyzing the kinetic resolution of various epoxides to enantiopure β-nitroalcohols with nitro-bearing stereocenters in up to 41 % isolated yield and >99 % enantiomeric excess (ee). Additionally, the bio-nitration method displays a high reaction efficiency and can be performed on a gram scale. We also solved the crystal structure of HHDHamb to understand the possible structural determinants of chemoselectivity control in the bio-nitration reaction.
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