The native chlorination function of Chloroperoxidase (CPO) is accompanied by a wide spectrum of additional catalytic activities. The stereoselective epoxidations of olefins attract attention as chiral epoxides are useful synthons for practical purposes. We present a study of CPO-catalyzed epoxidation of cis-�-methylstyrene (CBMS). In the presence of hydrogen peroxide CBMS is converted by CPO into 1S2R and 1R2S epoxide products with a 96:4 ratio. Our previous study of the CPO/CBMS complex showed that 1S2R and 1R2S binding wells do not provide significant differentiation to explain the enantiomeric excess. The enatiospecificity therefore, is likely to be caused by the active site effects on the transition states. Using quantum and classical mechanics methods we have studied the CPO/CBMS 1S2R transition state (TS). Key interaction/structure motifs were identified for the TS bound into the active site. The results presented should prove useful for further studies on the enantiospecificity of the CPO-catalyzed epoxidations.

Molecular dynamic study of 1S2R transition state in Chloroperoxidase-catalyzed epoxidation of Cis-β-Methylstyrene

243rd National Meeting (2012)

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