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  • Title: Determination of the absolute configuration and solution conformation of gossypol by vibrational circular dichroism.
    Author: Freedman TB, Cao X, Oliveira RV, Cass QB, Nafie LA.
    Journal: Chirality; 2003 Feb; 15(2):196-200. PubMed ID: 12520512.
    Abstract:
    Vibrational circular dichroism (VCD) measurements and density functional theory (DFT) calculations were used to obtain the first definitive assignment of the absolute configuration for the polyphenolic binaphpthyl dialdehyde gossypol and a determination of the solution conformation in CDCl(3). VCD spectra recorded for the two resolved enantiomers are near mirror images and excellent agreement between the observed IR and VCD spectra and intensity calculations carried out at the DFT (B3LYP/6-31G*) level establish the absolute configurations of (+)-gossypol as P and (-)-gossypol as M, with two conformations in CDCl(3) solution that differ in isopropyl group orientation.
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