Absolute configuration determination of isoflavan-4-ol stereoisomers
- Authors
- Kim, Mihyang; Won, Dongho; Han, Jaehong
- Issue Date
- Aug-2010
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Keywords
- ECD; Equol; Flavonoids; Stereochemistry; TD-DFT; VCD
- Citation
- BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, v.20, no.15, pp 4337 - 4341
- Pages
- 5
- Journal Title
- BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
- Volume
- 20
- Number
- 15
- Start Page
- 4337
- End Page
- 4341
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/22270
- DOI
- 10.1016/j.bmcl.2010.06.074
- ISSN
- 0960-894X
1464-3405
- 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. (C) 2010 Elsevier Ltd. All rights reserved.
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