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Photoinduced promiscuity of cyclohexanone monooxygenase for the enantioselective synthesis of α-deuterated carbonyl compounds
Molecular Catalysis ( IF 3.9 ) Pub Date : 2023-11-25 , DOI: 10.1016/j.mcat.2023.113709
Yongzhen Peng , Kongchen Xia , Qi Wu

The direct asymmetric synthesis of deuterium compounds has gained increasing attention. Here we report the engineered cyclohexanone monooxygenase from Acinetobacter sp. NCIMB 9871 for the synthesis of chiral α-deuterated carbonyl compounds via enantioselective reductive dehalogenation. The engineered CHMO exhibited good chemoselectivity, stereoselectivity and d-incorporation (up to 92% yield, 98% e.e. and 96% d-incorporation) toward a series of α-halogen carbonyl compounds. This method was also used for the synthesis of deuterated drugs, which demonstrated its promising application in synthetic chemistry.



中文翻译:

环己酮单加氧酶的光诱导混杂用于对映选择性合成α-氘代羰基化合物

氘化合物的直接不对称合成越来越受到人们的关注。在这里,我们报道了来自不动杆菌属的工程环己酮单加氧酶。NCIMB 9871 用于通过对映选择性还原脱卤合成手性 α-氘代羰基化合物。工程化的 CHMO对一系列 α-卤代羰基化合物表现出良好的化学选择性、立体选择性和 d-掺入(高达 92% 产率、98% ee和 96% d-掺入)。该方法还用于合成氘代药物,这证明了其在合成化学中的广阔应用前景。

更新日期:2023-11-26
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