AI Article Synopsis
- Biocatalysis is now being used for reactions traditionally handled by synthetic catalysts, particularly in carbene transfer chemistries like olefin cyclopropanation.
- Using thermophilic bacterial globins, researchers developed new hemoprotein catalysts that can facilitate a unique reaction producing cyclopropyl ketones.
- The cyclopropyl ketone created can be further transformed into a crucial intermediate for the synthesis of grazoprevir, a drug for treating hepatitis C.
Article Abstract
Reactions that were once the exclusive province of synthetic catalysts can increasingly be addressed using biocatalysis. Through discovery of unnatural enzyme reactions, biochemists have significantly expanded the reach of enzymatic catalysis to include carbene transfer chemistries including olefin cyclopropanation. Here we describe hemoprotein cyclopropanation catalysts derived from thermophilic bacterial globins that react with diazoacetone and an unactivated olefin substrate to furnish a cyclopropyl ketone, a previously unreported reaction for enzyme catalysts. We further demonstrate that the resulting cyclopropyl ketone can be converted to a key cyclopropanol intermediate that occurs en route to the anti-hepatitis C drug grazoprevir.
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| http://dx.doi.org/10.1002/cbic.201800652 | DOI Listing |
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