Determination of the absolute configurations of synthetic daunorubicin analogues using vibrational circular dichroism spectroscopy and density functional theory.
The absolute configurations of three synthesized anthracycline analogues have been determined using vibrational circular dichroism (VCD) spectroscopy and the density functional theory (DFT) calculations. The experimental VCD spectra of the three compounds have been measured for the first time in the film state, prepared from their CDCl(3) solutions. Conformational searches for the monomers and some dimers of the three compounds have been performed at the DFT level using the B3LYP functional and the 6-311G** and 6-311++G** basis sets. The corresponding vibrational absorption and VCD spectra have been calculated. The good agreement between the experimental and the calculated spectra allows one to assign the absolute configurations of the three compounds with high confidence. In addition, the dominant conformers of the three compounds have also been identified.
Yang
Guochun
G
Department of Chemistry and Alberta Ingenuity Centre for Carbohydrate Science, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.
Tran
Ha
H
Fan
Eric
E
Shi
Wei
W
Lowary
Todd L
TL
Xu
Yunjie
Y
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D002942:Circular Dichroism; D003630:Daunorubicin / Q000031:analogs & derivatives* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D011789:Quantum Theory; D014732:Vibration
D000970:Antineoplastic Agents; D003630:Daunorubicin