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• W1997566620 abstract "The selective oxyfunctionalization of isolated sp3 C–H bonds in complex molecules represents a formidable challenge in organic chemistry. Here, we describe a rational, systematic strategy to expedite the development of P450 oxidation catalysts with refined regio- and stereoselectivity for the hydroxylation of remote, unactivated C–H sites in a complex scaffold. Using artemisinin as model substrate, we demonstrate how a three-tier strategy involving first-sphere active site mutagenesis, high-throughput P450 fingerprinting, and fingerprint-driven P450 reactivity predictions enabled the rapid evolution of three efficient biocatalysts for the selective hydroxylation of a primary and a secondary C–H site (with both S and R stereoselectivity) in a relevant yet previously inaccessible region of this complex natural product. The evolved P450 variants could be applied to provide direct access to the desired hydroxylated derivatives at preparative scales (0.4 g) and in high isolated yields (>90%), thereby enabling further elaboration of this molecule. As an example, enantiopure C7-fluorinated derivatives of the clinical antimalarial drugs artesunate and artemether, in which a major metabolically sensitive site is protected by means of a C–H to C–F substitution, were afforded via P450-mediated chemoenzymatic synthesis." @default.
• W1997566620 created "2016-06-24" @default.
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• W1997566620 date "2012-11-02" @default.
• W1997566620 modified "2023-10-17" @default.
• W1997566620 title "Controlled Oxidation of Remote sp³ C–H Bonds in Artemisinin via P450 Catalysts with Fine-Tuned Regio- and Stereoselectivity" @default.
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• W1997566620 doi "https://doi.org/10.1021/ja3073462" @default.
• W1997566620 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/3498520" @default.
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