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Award ID contains: 1513007

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  1. ; ; ; ; ; (, ACS Catalysis)
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  2. ; ; (, Journal of the American Chemical Society)
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  3. ; (, Journal of the American Chemical Society)
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  4. ; (, Nature Catalysis)
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  5. ; ; ; (, Journal of the American Chemical Society)
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  6. ; ; ; ; (, Nature Chemistry)
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  7. ; ; ; (, Journal of the American Chemical Society)
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  8. ; ; ; ; ; ; (, Synlett)
    Previous work has demonstrated that variants of a heme protein, Rhodothermus marinus cytochrome c (Rma cyt c), catalyze abiological carbene boron–hydrogen (B–H) bond insertion with high efficiency and selectivity. Here we investigated this carbon–boron bond-forming chemistry with cyclic, lactone-based carbenes. Using directed evolution, we obtained a Rma cyt c variant BORLAC that shows high selectivity and efficiency for B–H insertion of 5- and 6-membered lactone carbenes (up to 24,500 total turnovers and 97.1:2.9 enantiomeric ratio). The enzyme shows low activity with a 7-membered lactone carbene. Computational studies revealed a highly twisted geometry of the 7-membered lactone carbene intermediate relative to 5- and 6-membered ones. Directed evolution of cytochrome c together with computational characterization of key iron-carbene intermediates has allowed us to expand the scope of enzymatic carbene B–H insertion to produce new lactone-based organoborons. 
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  9. ; ; ; ; ; ; (, ACS Central Science)