title: Absolute configuration determination of isoflavan-4-ol stereoisomers.
abstract: 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.
authors.affiliation: Metalloenzyme Research Group and Department of Biotechnology, Chung-Ang University, Anseong 456-756, Republic of Korea.
authors.forename: Mihyang
authors.initials: M
authors.lastname: Kim
authors.forename: Dongho
authors.initials: D
authors.lastname: Won
authors.forename: Jaehong
authors.initials: J
authors.lastname: Han
mesh_terms: D002942:Circular Dichroism; D007529:Isoflavones / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D007529:Isoflavones