Absolute configuration determination of isoflavan-4-ol stereoisomers

作者：Kim Mihyang; Won Dongho; Han Jaehong^*

来源：Bioorganic & Medicinal Chemistry Letters, 2010, 20(15): 4337-4341.

DOI：10.1016/j.bmcl.2010.06.074

• ECD
• Equol
• Flavonoids
• Stereochemistry
• TD-DFT
• VCD

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.

• 出版日期2010-8-1