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In this study, we constructed a taxadiene overproduction platform and identified a cytochrome P450, CYP701A8, that activates the inert C–H bonds in taxadiene to produce three oxidized products (1–3). Compound 1 possesses a newly identified 1 (15→11) abeotaxane skeleton, while 3 features a distinctive 6/10-fused carbocyclic core with an α,β-unsaturated ketone moiety. Our quantum computations suggested a carbocation-driven rearrangement in the formation of 1. These results support CYP701A8 as a promising biocatalyst for the generation of novel taxane diterpenoids.
Xiao et al. (Wed,) studied this question.