Cytochrome P450-Mediated Skeleton Rearrangement of Taxadiene in an Engineered <i>Escherichia coli</i> System

Abstract

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.

Topics & Concepts