Synthesis of Chiral 5‐Aryl‐2‐oxazolidinones via Halohydrin Dehalogenase‐Catalyzed Enantio‐ and Regioselective Ring‐Opening of Styrene Oxides
Nan‐Wei Wan, Xiaoying Zhou, Ran Ma, Jiawei Tian, Huihui Wang, Bao‐Dong Cui, Wen‐Yong Han, Yong‐Zheng Chen
Abstract
Abstract An efficient biocatalytic approach for enantio‐ and regioselective ring‐opening of styrene oxides with cyanate was developed by using the halohydrin dehalogenase HheC from Agrobacterium radiobacter AD1, generating the corresponding chiral 5‐aryl‐2‐oxazolidinones in up to 47% yield and 90% ee. Additionally, the origin of enantioselectivity and regioselectivity of the HheC‐catalyzed cyanate‐mediated ring‐opening process was uncovered by single enantiomer bioconversions and molecular docking study. magnified image
Topics & Concepts
RegioselectivityChemistryCyanateArylEnantiomerStyreneRing (chemistry)Combinatorial chemistryCatalysisStereochemistryOrganic chemistryCopolymerPolymerAlkylEnzyme Catalysis and ImmobilizationMicrobial Metabolic Engineering and BioproductionMicrobial bioremediation and biosurfactants