Buagafuran is a novel drug candidate derived from natural product.Its absolute configuration has been confirmed by electronic circular dichroism combined with modern quantum-chemical calculation using time-dependent d...Buagafuran is a novel drug candidate derived from natural product.Its absolute configuration has been confirmed by electronic circular dichroism combined with modern quantum-chemical calculation using time-dependent density functional theory.The predicted UV absorbance peak is underestimated by several nanometers compared with the experimental data.The applicability of empirical rule for the C=C-C-O system in Buagafuran has also been discussed.Our results show that electronic circular dichroism could be a useful tool for the absolute configuration assignment of chiral drugs,especially for the oily or semisolid substances,whose crystal structures are impossible to obtain.展开更多
Since two asymmetric centres are usually present in the bisbenzylisoquinolines,the circular dichroism is known to be an important method to elucidate their stereochemistry.We studied the relationships of the CD spectr...Since two asymmetric centres are usually present in the bisbenzylisoquinolines,the circular dichroism is known to be an important method to elucidate their stereochemistry.We studied the relationships of the CD spectra with the stereochemistry of synthetic RR-(1),SS-(2),RS-daurisoline(3) and SR-daurisoline(4).By comparision of the CD spectrum of natural daurisoline(1)from Menis- permum dauricum(Menispermaceae)with those of synthetic enantiomers,the absolute configuration was established as RR-daurisoline(1).展开更多
基金supported by the Fundamental Research Funds for the Central Institutes(No.2012ZD03)
文摘Buagafuran is a novel drug candidate derived from natural product.Its absolute configuration has been confirmed by electronic circular dichroism combined with modern quantum-chemical calculation using time-dependent density functional theory.The predicted UV absorbance peak is underestimated by several nanometers compared with the experimental data.The applicability of empirical rule for the C=C-C-O system in Buagafuran has also been discussed.Our results show that electronic circular dichroism could be a useful tool for the absolute configuration assignment of chiral drugs,especially for the oily or semisolid substances,whose crystal structures are impossible to obtain.
基金This work was supported by the National Natural Science Foundation of China.
文摘Since two asymmetric centres are usually present in the bisbenzylisoquinolines,the circular dichroism is known to be an important method to elucidate their stereochemistry.We studied the relationships of the CD spectra with the stereochemistry of synthetic RR-(1),SS-(2),RS-daurisoline(3) and SR-daurisoline(4).By comparision of the CD spectrum of natural daurisoline(1)from Menis- permum dauricum(Menispermaceae)with those of synthetic enantiomers,the absolute configuration was established as RR-daurisoline(1).
