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Absolute Configurations of (+/-)-Glabridin Enantiomers
- Authors
- Kim, Mihyang; Kim, Soo-Un; Kim, Yong-ung; Han, Jaehong
- Issue Date
- Feb-2009
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- Absolute configuration; Circular dichroism (CD); Flavonoids; Glabridin; Isoflavan
- Citation
- BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.30, no.2, pp 415 - 418
- Pages
- 4
- Journal Title
- BULLETIN OF THE KOREAN CHEMICAL SOCIETY
- Volume
- 30
- Number
- 2
- Start Page
- 415
- End Page
- 418
- ISSN
- 1229-5949
1229-5949
- Abstract
- Concerned with ambiguous stereochemistry assignment of natural (+)-glabridin, absolute configurations of (+/-)-glabridin enantiomers were studied with synthetic glabridin. Synthetic glabridin enantiomers were separated by semi-preparative Sumi-chiral column chromatography, and characterized by UV-Vis and NMR spectroscopy. Three-dimensional molecular structure of glabridin was obtained as equatorial Ph-3 half chair chroman ring from semi-empirical PM3 calculation, and refined by coupling constants in H-1 NMR spectrum. Finally, absolute configurations of two enantiomers were determined by circular dichroism spectroscopy based on the empirical helicity rules. Absolute configuration of natural (+)-glabridin was confirmed as (R)-glabridin, as known.
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