Vitreoscillahemoglobin: a natural carbene transfer catalyst for diastereo- and enantioselective synthesis of nitrile-substituted cyclopropanes

Abstract

we developed an environmentally friendly strategy that combines in situ generation of a diazo reagent with biocatalysis for the asymmetric cyclopropanation of olefins.

Efficient Synthesis of Pyrrole Disulfides Catalyzed by Lipase in Ethanol

“…Enzymes display a high degree of specificity toward the reactions they catalyze, a characteristic termed as "specificity". However, when studied outside their natural context, some enzymes can catalyze a variety of different chemical reactions or act on multiple substrates, such as hemoproteins [19,20], Baeyer-Villiger monooxygenase [21], transaminases [22] and laccase [23]. This phenomenon is referred to as "catalytic promiscuity".…”

Directed evolution of Escherichia coli surface-displayed Vitreoscilla hemoglobin as an artificial metalloenzyme for the synthesis of 5-imino-1,2,4-thiadiazoles

“…To circumvent the limitation of the directed evolution of VHb Co based on our previous studies, 34,35,46,47 we developed a new approach that uses E. coli surface-displayed method. We created a platform to display VHb Co on E. coli 's outer membrane (VHb SD-Co ) and established a whole-cell high-throughput screening strategy based on ultraviolet (UV) absorption for the in vivo directed evolution of VHb SD-Co with high catalytic reactivity for the synthesis of 5-imino-1,2,4-thiadiazoles.…”

Biocatalytic Enantioselective Reduction of Cyclopropenyl Esters and Ketones Using Ene-Reductases

“…The most classical methods to produce chiral cyclopropanes are the addition of active intermediates on alkenes (Simmons-Smith Furukawa cyclopropanation, the Corey-Chaykovsky cyclopropanation, metal-catalyzed decomposition of diazoesters), esters (Kulinkovich reaction), and formamides (De Meijere reaction). More recently the biocatalytic version of the Corey-Chaykovsky cyclopropanation has been reported, as well as the biocatalytic version of the addition of diazo compounds on olefins . Optically active cyclopropanes can also be obtained by intra- and intermolecular direct functionalization of achiral cyclopropanes by C–H bond activation .…”