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Engineered heme proteins can build chiral cyclopropenes and bicyclobutanes by adding carbene units to carbon–carbon double bonds. In a 2018 study, researchers used directed evolution to give these proteins a non-natural catalytic activity, then demonstrated the reaction in living Escherichia coli and at preparative scale. The result is a laboratory synthesis method—not evidence of an industrial process or a consumer product.
How can an enzyme make a bicyclobutane?
The team repurposed heme proteins, which contain an iron–porphyrin cofactor, to transfer a carbene unit onto an unsaturated carbon–carbon bond. A carbene is a carbon-containing reactive unit that can add to the bond and close it into a small ring.
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One carbene addition can form a cyclopropene, a three-membered carbon ring containing a double bond. Successive additions can produce a bicyclobutane, a compact framework made of two fused three-membered rings. The paper describes cyclopropene-forming enzymes as producing putative intermediates on the route to bicyclobutanes.
This was not the discovery of a natural biological pathway. The researchers used directed evolution—repeatedly modifying and selecting proteins for improved activity—to develop enzymes that catalyze a reaction not known to occur in nature. The engineered proteins were genetically encoded and functional in E. coli. The 2018 Science paper describes the engineering of heme proteins for these reactions.
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What did the study demonstrate?
The authors reported that their enzymes worked on structurally diverse substrates with high efficiency and selectivity, and that the resulting products could be further derivatized. The products are chiral: they can exist in forms that are mirror images of one another. Enzyme control over which form is produced is an important part of the method.
Chemistry World’s 2018 report says the researchers synthesized 25 different compounds. That figure describes the reported substrate breadth; it should not be read as a count of commercial products or evidence of industrial-scale manufacture.
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The primary paper also describes the biotransformation as readily performed at preparative scale. That establishes a useful scale for preparing compounds for research and further chemistry, but it does not by itself establish commercial production or a broad advantage over conventional synthesis routes.
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Small carbon rings force bonds and bond angles into geometries that are less comfortable than those found in many larger rings. The resulting stored energy is called ring strain. The Science article gives approximate strain energies of 54 kcal/mol for cyclopropenes with an endocyclic double bond and about 66 kcal/mol for bicyclo[1.1.0]butanes. These are estimates for the highlighted ring systems, not fixed values for every substituted molecule.
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That strain is also useful. Reactions that release it can help chemists transform the rings into other molecular frameworks, making strained carbocycles potentially valuable intermediates for chemical and materials synthesis. The study demonstrates a way to construct such frameworks; it does not establish a specific downstream product or application.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.What the result does—and does not—mean
- Demonstrated: Engineered heme proteins catalyzed carbene additions that form chiral cyclopropenes and bicyclobutanes.
- Demonstrated: The proteins functioned in E. coli, and the authors reported diverse substrates, high efficiency and selectivity, and preparative-scale biotransformation.
- Not established by this study: Industrial adoption, commercial availability of a resulting product, or universal superiority to conventional synthetic methods.
Caltech’s research record states that plasmids encoding the enzymes were available for research purposes from Frances H. Arnold under a material transfer agreement, and that three authors were inventors on a Caltech patent application covering biocatalytic synthesis of strained carbocycles. Those are disclosures from the time of the record, not confirmation of present-day access, patent status, or licensing terms. Caltech’s research record provides that historical context.
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