Absolute configuration determination of isoflavan-4-ol stereoisomers.
Elucidation of the correct stereochemistry of the metabolite is essential for the mechanistic study of bioactive compounds. Isoflavan-4-ol has the same chiropical chromophore as THD, the biosynthetic precursor of the potent phytoestrogen S-equol. Interested in the correct absolute configuration of isoflavan-4-ol stereoisomers and to compare the available practical approaches for the absolute configuration determination, complete absolute configuration analysis of isoflavan-4-ol stereoisomers has been carried out with by means of ECD and VCD spectroscopy as well as modified Mosher method. Theoretical TD-DFT computations resulted in a poor simulation of the observed experimental ECD spectra, and thus inconclusive absolute configuration assignments of isoflavan-4-ol stereoisomers were obtained. However, DFT-assisted VCD spectroscopic analyses successfully determined correct absolute configurations, and further confirmed by modified Mosher method.
Kim
Mihyang
M
Metalloenzyme Research Group and Department of Biotechnology, Chung-Ang University, Anseong 456-756, Republic of Korea.
Won
Dongho
D
Han
Jaehong
J
D002942:Circular Dichroism; D007529:Isoflavones / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
D007529:Isoflavones