Journal
SCIENCE
Volume 339, Issue 6117, Pages 307-310Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.1231434
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- Division of Chemical Sciences, Geosciences, and Biosciences, Office of Basic Energy Sciences of the U.S. Department of Energy [DE-FG02-06ER15762]
- Ruth M. Kirschstein National Institutes of Health (NIH) from the National Institute of General Medical Sciences [F32GM087102]
- University of North Carolina Chapel Hill
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Transition metal-catalyzed transfers of carbenes, nitrenes, and oxenes are powerful methods for functionalizing C = C and C-H bonds. Nature has evolved a diverse toolbox for oxene transfers, as exemplified by the myriad monooxygenation reactions catalyzed by cytochrome P450 enzymes. The isoelectronic carbene transfer to olefins, a widely used C-C bond-forming reaction in organic synthesis, has no biological counterpart. Here we report engineered variants of cytochrome P450(BM3) that catalyze highly diastereo- and enantioselective cyclopropanation of styrenes from diazoester reagents via putative carbene transfer. This work highlights the capacity to adapt existing enzymes for the catalysis of synthetically important reactions not previously observed in nature.
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