The Reactivity of α-Fluoroketones with PLP Dependent Enzymes: Transaminases as Hydrodefluorinases,ChemCatChem

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The Reactivity of α-Fluoroketones with PLP Dependent Enzymes: Transaminases as Hydrodefluorinases
ChemCatChem ( IF 3.8 ) Pub Date : 2021-07-19 , DOI: 10.1002/cctc.202100901
Marina García-Ramos ₁ , Aníbal Cuetos ₂ , Wolfgang Kroutil ₃ , Gideon Grogan ₂ , Ivan Lavandera ₄

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A chemical method for the treatment of harmful halogenated compounds that has recently become of interest is the reductive dehalogenation of carbon-halogen bonds. In the case of a fluorine atom, this process is called hydrodefluorination. While many transition metal-based approaches now exist to reductively defluorinate aromatic fluoroarenes, the cleavage of C−F bonds in aliphatic compounds is not so well-developed. Here we propose a biocatalytic approach exploiting a promiscuous activity exhibited by transaminases (TAs). Hence, a series of α-fluoroketones have been defluorinated with excellent conversions using Chromobacterium violaceum and Arthrobacter sp. TAs under mild conditions and in aqueous medium, using a stoichiometric amount of an amine (e. g. 2-propylamine) as reagent and formally releasing its oxidized form (e. g. acetone), with ammonia and hydrogen fluoride as by-products. It is also demonstrated that this process can be performed in a regio- or stereoselective fashion.

中文翻译：

α-氟酮与 PLP 依赖性酶的反应性：转氨酶作为氢化脱氟酶

最近引起关注的一种用于处理有害卤化化合物的化学方法是碳-卤键的还原脱卤。在氟原子的情况下，该过程称为加氢脱氟。虽然现在存在许多基于过渡金属的方法来对芳族氟芳烃进行还原脱氟，但脂肪族化合物中 C-F 键的裂解还没有得到很好的发展。在这里，我们提出了一种利用转氨酶 (TA) 表现出的混杂活性的生物催化方法。因此，一系列 α-氟酮已经使用紫色色杆菌和节杆菌属以优异的转化率脱氟。在温和条件下和水性介质中，使用化学计量的胺（例如. 2-丙胺）作为试剂并正式释放其氧化形式（例如丙酮），氨和氟化氢作为副产物。还证明了该过程可以以区域或立体选择性方式进行。

更新日期：2021-09-17

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