Journal
SCIENCE
Volume 360, Issue 6384, Pages 71-+Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aar4239
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Funding
- NSF Division of Molecular and Cellular Biosciences [MCB-1513007]
- Ruth L. Kirschstein NIH Postdoctoral Fellowship [F32GM125231]
- NSF Graduate Research Fellowship [DGE-1144469]
- Donna and Benjamin M. Rosen Bioengineering Center
- Div Of Molecular and Cellular Bioscience
- Direct For Biological Sciences [1513007] Funding Source: National Science Foundation
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Small carbocycles are structurally rigid and possess high intrinsic energy due to their ring strain. These features lead to broad applications but also create challenges for their construction. We report the engineering of hemeproteins that catalyze the formation of chiral bicyclobutanes, one of the most strained four-membered systems, via successive carbene addition to unsaturated carbon-carbon bonds. Enzymes that produce cyclopropenes, putative intermediates to the bicyclobutanes, were also identified. These genetically encoded proteins are readily optimized by directed evolution, function in Escherichia coil, and act on structurally diverse substrates with high efficiency and selectivity, providing an effective route to many chiral strained structures. This biotransformation is easily performed at preparative scale, and the resulting strained carbocycles can be derivatized, opening myriad potential applications.
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