GoKawiilEngineered haemproteins turn simple alkenes into chiral oxazolidinones
Researchers developed a haemprotein biocatalyst that performs aziridination followed by ring expansion, directly converting unactivated alkenes into enantioselective oxazolidinones. This approach installs the previously hard-to-achieve 5-stereocentre in these heterocycles, which are key scaffolds in next-generation tuberculosis antibiotics. The method extends haemprotein nitrene-transfer chemistry beyond conjugated substrates like styrenes to simple, unactivated alkenes.
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By enabling enantioselective synthesis from simple starting materials, this biocatalytic route could simplify production of oxazolidinone-based drug candidates that currently depend on complex chiral-pool synthesis. The researchers' computational analysis attributes the enzyme's selectivity to specific mutations from directed evolution, suggesting a rational path to further engineer such biocatalysts for other challenging heterocycle targets. This could broaden the toolkit for synthesizing antibiotics aimed at drug-resistant tuberculosis.
- A haemprotein catalyst performs aziridination/ring-expansion to make chiral oxazolidinones from unactivated alkenes
- The method installs the difficult 5-stereocentre relevant to next-gen tuberculosis antibiotic scaffolds
- Directed evolution mutations, analyzed computationally, explain the enzyme's enantioselectivity
Source: nature.com — Li, 2026-09-23
Published there as: “Chiral oxazolidinones <i>via</i> biocatalytic aziridination of unactivated alkenes”
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