Stereoselective olefin cyclopropanation under aerobic conditions with an artificial enzyme incorporating an iron-chlorin e6 cofactor.

ABSTRACT: Myoglobin has recently emerged as a promising biocatalyst for catalyzing carbene-mediated cyclopropanation, a synthetically valuable transformation not found in nature. Having naturally evolved for binding dioxygen, the carbene transferase activity of this metalloprotein is severely inhibited by it, imposing the need for strictly anaerobic conditions to conduct these reactions. In this report, we describe how substitution of the native heme cofactor with an iron-chlorin e6 complex enabled the development of a biocatalyst capable of promoting the cyclopropanation of vinylarenes with high catalytic efficiency (up to 6,970 TON), turnover rate (>2,000 turnovers/min), and stereoselectivity (up to 99% de and ee) in the presence of oxygen. The artificial metalloenzyme can be recombinantly express

SUBMITTER: Sreenilayam G 

PROVIDER: S-EPMC5863724 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature