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2.6.1.5.2 Engineered Cytochrome P450 Epoxidation of Styrene and Substituted Styrenes

DOI: 10.1055/sos-SD-215-00272

Li, A. T.; Li, Z.Science of Synthesis: Biocatalysis in Organic Synthesis, (20152495.

Recently, protein engineering and directed evolution have been applied to create P450 enzyme mutants with improved enzyme activity and enantioselectivity. Several P450BM3 mutants have been obtained that produce the R-epoxides with significantly improved enantioselectivity. For instance, epoxidation of styrene (20, Ar1 = Ph) and 3-chlorostyrene (20, Ar1 = 3-ClC6H4) with the P450 BM3-F87G (Phe87Gly) mutant gives the corresponding R-epoxides 21 in 92 (Ar1 = Ph) and 94.6% (Ar1 = 3-ClC6H4) enantiomeric excess, respectively (Scheme 11).[‌99‌,‌100‌]

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References


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