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Engineered heme proteins can build chiral cyclopropenes and bicyclobutanes by transferring carbene units to carbon–carbon bonds. In a 2018 Science study, researchers used directed evolution to give these proteins a non-natural reaction that makes compact, highly strained carbon rings—an advance in laboratory synthesis, not an established industrial process.
How can an enzyme make a bicyclobutane?
The team repurposed heme proteins, which contain an iron–porphyrin cofactor, to transfer carbene units onto unsaturated carbon–carbon bonds. A carbene addition can form a cyclopropene; successive additions can build a bicyclobutane. The study describes cyclopropene-forming enzymes as producing putative intermediates on the route to bicyclobutanes.
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This was not a known natural biological pathway. The researchers used directed evolution to develop and improve the enzymes’ new activity. The genetically encoded proteins also functioned in Escherichia coli, providing a biological setting for the engineered chemistry.
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The enzymes produced chiral products, so their ability to control stereochemistry was part of the achievement. The primary research record reports high efficiency and selectivity across structurally diverse substrates, along with a biotransformation that was readily performed at preparative scale. The products could also be derivatized, meaning they could be chemically modified for further synthesis.
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Chemistry World reported in 2018 that the researchers synthesized 25 different compounds. That figure describes the breadth reported in that news account; it is not evidence of commercial-scale production. The study establishes a useful synthetic approach, but does not show that it outperforms every conventional route.
What makes these rings “super strained”?
Small rings force their atoms into bonding arrangements that are less comfortable than those in many larger, more flexible structures. The resulting ring strain can make these compounds challenging to construct, while also making them useful starting points: reactions that release strain can open routes to other molecular frameworks.
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Chen and colleagues give approximate ring-strain energies of about 54 kcal/mol for cyclopropenes with an endocyclic double bond and around 66 kcal/mol for bicyclo[1.1.0]butanes. These are estimates for the highlighted ring systems, not exact values that apply identically to every substituted molecule.
What the result does—and does not—mean
The work shows that engineered proteins can perform non-natural carbene-transfer chemistry with useful selectivity and can make strained carbocycles at preparative scale. It is a laboratory research result, not proof of an established industrial process or a consumer product. Caltech’s research record described research access to the enzyme-encoding plasmids under a material transfer agreement and disclosed a patent application by three of the study’s authors; those historical statements do not establish current availability, patent status, or licensing terms.
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