Absolute Configuration of the Polyketide Natural Product (-)-Enterocin

The absolute configuration of the polyketide natural product (-)-enterocin was established by two independent approaches. In the first approach, synthetic enterocin with a defined configuration was compared to the natural product. While identical in all scalar properties, the compound displayed an opposite specific rotation and a different chiral HPLC retention time when compared with (-)-enterocin. In a second approach, the vibrational circular dichroism (VCD) of the natural product was measured and shown to be opposite to the calculated VCD of its enantiomer.

Automated summary

The absolute configuration of the polyketide natural product (-)-enterocin was determined using two independent approaches. By comparing synthetic enterocin with a defined configuration to the natural product, and by measuring the vibrational circular dichroism (VCD), the absolute configuration of (-)-enterocin was confirmed.