Planta Med 2013; 79 - PO14
DOI: 10.1055/s-0033-1348794

Recent Applications of Vibrational Circular Dichroism (VCD) in Determination of Absolute Configurations of Chiral Natural Products

Y He 1, B Wang 1, RK Dukor 1, LA Nafie 2, C Salomon 3
  • 1BioTools Inc., 17546 Beeline Hwy, Jupiter, FL 33458
  • 2Department of Chemistry, 1 – 014 CST, Syracuse University, Syracuse, NY 13244
  • 3Center for Drug Design, University of Minnesota, MMC 204, 462a VFW Cancer Research Bldg., 406 Harvard St. SE, Minneapolis, MN 55455

Determination of absolute configuration (AC) of chiral molecules is an important step in any field related to chirality, especially in the pharmaceutical industry. Vibrational circular dichroism (VCD) has become a powerful tool for the determination of absolute configuration of chiral molecules in solution state after 30 years of evolution. VCD offers a novel alternative to X-ray crystallography, permitting AC determinations on neat liquid, oil, and solution samples. By comparing the sign and intensity of the experimental VCD spectrum with the ab initio DFT calculated VCD of a chosen configuration, one can unambiguously assign the absolute configuration of a chiral molecule. Comparing measured VCD spectra with calculated VCD spectra of all the conformers can also provide solution-state conformational populations. In this poster several recent application of VCD to the determination of absolute configuration of chiral natural product molecules are presented. In the case of Colomitide study, the absolute configuration of the single enantiomer natural product molecule with five unknown chiral centers was successfully determined by VCD method.