1. Absolute configuration determination of isoflavan-4-ol stereoisomers
- Author
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Kim, Mihyang, Won, Dongho, and Han, Jaehong
- Subjects
- *
ORGANIC compounds , *STEREOISOMERS , *STEREOCHEMISTRY , *METABOLITES , *BIOACTIVE compounds , *BIOSYNTHESIS , *PHYTOESTROGENS , *THERAPEUTICS - Abstract
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. [Copyright &y& Elsevier]
- Published
- 2010
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