Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 15, Pages 4711-4715Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201601056
Keywords
amination; biocatalysis; cytochrome P450; directed evolution; nitrene transfer
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Funding
- National Science Foundation, Division of Molecular and Cellular Biosciences [MCB-1513007]
- Resnick Sustainability Institute
- Ruth L. Kirschstein National Research Service Award [F32GM108143]
- NSF Graduate Research Fellowship
- Direct For Biological Sciences
- Div Of Molecular and Cellular Bioscience [1513007] Funding Source: National Science Foundation
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Sigmatropic rearrangements, while rare in biology, offer opportunities for the efficient and selective synthesis of complex chemical motifs. A P411 serine-ligated variant of cytochrome P450(BM3) has been engineered to initiate a sulfimidation/[2,3]-sigmatropic rearrangement sequence in whole E. coli cells, a non-natural function for any enzyme, providing access to enantioenriched, protected allylic amines. Five mutations in the enzyme substantially enhance its activity toward this new function, demonstrating the evolvability of the catalyst toward challenging nitrene transfer reactions. The evolved catalyst additionally performs the highly enantioselective imidation of non-allylic sulfides.
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