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- W4386826512 abstract "Abstract The stereocontrolled cationic cyclization cascade is a vital step in the modular biogenesis of terpenes, as it defines the carbon skeleton's three-dimensional structure in one atom-economical step. While nature has adopted this strategy for eons, state-of-the-art synthetic routes to asymmetrically access cyclic terpenes still rely predominantly on sequential multi-step scaffold remodelling of a few abundant precursors. Herein, we bridge this long-standing methodological gap and demonstrate the target-oriented synthesis ability of the squalene-hopene cyclase. Our mechanistic insights show that the biocatalytic head-to-tail cyclization is highly customizable by mechanism-guided enzyme engineering and substrate-focused setup engineering. As a result, we demonstrate two- or three-step hybrid synthetic routes of pheromones, fragrances, and drug candidates by merging a stereocontrolled cyclization with interdisciplinary synthetic and catalytic methods. This biomimetic strategy significantly reduces the synthesis effort to terpenes and provides rapid access to thousands of head-to-tail-fused scaffolds." @default.
- W4386826512 created "2023-09-19" @default.
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- W4386826512 date "2023-09-18" @default.
- W4386826512 modified "2023-09-27" @default.
- W4386826512 title "Biocatalytic stereocontrolled head-to-tail cyclizations as a tool for streamlined hybrid synthesis of terpenes" @default.
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- W4386826512 doi "https://doi.org/10.21203/rs.3.rs-3207290/v1" @default.
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