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Artificial Metalloenzymes for Asymmetric Allylic Alkylation on the Basis of the Biotin–Avidin Technology

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  • This research was supported by the Canton of Neuchâtel, the Swiss National Science Foundation (grants FN 200021-105192 and 200020-113348), the Roche Foundation, and the FP6 Marie Curie Research Training Network (IBAAC MRTN-CT-2003-505020). Umicore Precious Metals Chemistry is acknowledged for a loan of palladium, and Belovo for a generous gift of avidin. We thank Prof. C. R. Cantor for providing us with the streptavidin gene.

Abstract

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Palladium in the active site: The incorporation of a biotinylated palladium diphosphine within streptavidin yielded an artificial metalloenzyme for the title reaction (see scheme). Chemogenetic optimization of the catalyst by the introduction of a spacer (red star) between biotin (green triangle) and palladium and saturation mutagenesis at position S112X afforded both R- and S-selective artificial asymmetric allylic alkylases.

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