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Determination of the absolute configurations of synthetic daunorubicin analogues using vibrational circular dichroism spectroscopy and density functional theory
Author(s) -
Yang Guochun,
Tran Ha,
Fan Eric,
Shi Wei,
Lowary Todd L.,
Xu Yunjie
Publication year - 2010
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20825
Subject(s) - chemistry , vibrational circular dichroism , density functional theory , conformational isomerism , circular dichroism , spectroscopy , absolute configuration , chirality (physics) , time dependent density functional theory , spectral line , absorption spectroscopy , computational chemistry , crystallography , molecule , stereochemistry , organic chemistry , chiral symmetry , physics , nambu–jona lasinio model , quantum mechanics , astronomy , quark
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. Chirality, 2010. © 2010 Wiley‐Liss, Inc.