氟
黄素组
组合化学
酶
化学
激进的
有机化学
立体化学
作者
Mao‐Lin Li,Yujie Yuan,Wesley Harrison,Zhengyi Zhang,Huimin Zhao
出处
期刊:Science
[American Association for the Advancement of Science (AAAS)]
日期:2024-07-26
卷期号:385 (6707): 416-421
被引量:1
标识
DOI:10.1126/science.adk8464
摘要
Enzymes capable of assimilating fluorinated feedstocks are scarce. This situation poses a challenge for the biosynthesis of fluorinated compounds used in pharmaceuticals, agrochemicals, and materials. We developed a photoenzymatic hydrofluoroalkylation that integrates fluorinated motifs into olefins. The photoinduced promiscuity of flavin-dependent ene-reductases enables the generation of carbon-centered radicals from iodinated fluoroalkanes, which are directed by the photoenzyme to engage enantioselectively with olefins. This approach facilitates stereocontrol through interaction between a singular fluorinated unit and the enzyme, securing high enantioselectivity at β, γ, or δ positions of fluorinated groups through enzymatic hydrogen atom transfer-a process that is notably challenging with conventional chemocatalysis. This work advances enzymatic strategies for integrating fluorinated chemical feedstocks and opens avenues for asymmetric synthesis of fluorinated compounds.
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