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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 2
BKCSDE 30(2)
February 20, 2009 

Absolute Configurations of (±)-Glabridin Enantiomers
Mihyang Kim, Soo Un Kim, Yong ung Kim, Jaehong Han*
Absolute configuration, Circular dichroism (CD), Flavonoids, Glabridin, Isoflavan
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 1H 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.
415 - 418
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