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Anti-Markovnikov alkene oxidation by metal-oxo-mediated enzyme catalysis.
- Source :
-
Science (New York, N.Y.) [Science] 2017 Oct 13; Vol. 358 (6360), pp. 215-218. - Publication Year :
- 2017
-
Abstract
- Catalytic anti-Markovnikov oxidation of alkene feedstocks could simplify synthetic routes to many important molecules and solve a long-standing challenge in chemistry. Here we report the engineering of a cytochrome P450 enzyme by directed evolution to catalyze metal-oxo-mediated anti-Markovnikov oxidation of styrenes with high efficiency. The enzyme uses dioxygen as the terminal oxidant and achieves selectivity for anti-Markovnikov oxidation over the kinetically favored alkene epoxidation by trapping high-energy intermediates and catalyzing an oxo transfer, including an enantioselective 1,2-hydride migration. The anti-Markovnikov oxygenase can be combined with other catalysts in synthetic metabolic pathways to access a variety of challenging anti-Markovnikov functionalization reactions.<br /> (Copyright © 2017 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works.)
Details
- Language :
- English
- ISSN :
- 1095-9203
- Volume :
- 358
- Issue :
- 6360
- Database :
- MEDLINE
- Journal :
- Science (New York, N.Y.)
- Publication Type :
- Academic Journal
- Accession number :
- 29026041
- Full Text :
- https://doi.org/10.1126/science.aao1482