Determination of the Absolute Configurations of Synthetic Daunorubicin Analogues Using Vibrational Circular Dichroism Spectroscopy and Density Functional Theory

作者：Yang Guochun; Tran Ha; Fan Eric; Shi Wei; Lowary Todd L; Xu Yunjie^*

来源：Chirality, 2010, 22(8): 734-743.

DOI：10.1002/chir.20825

• vibrational circular dichroism
• vibrational absorption
• density functional calculations
• anthracycline analogues
• film technique

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 CDCl3 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 6-31111G** 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. Chirality 22: 734-743, 2010.

• 出版日期2010-8