Absolute Configurations of (±)-Glabridin Enantiomers

Concerned with ambiguous stereochemistry assignment of natural (+)-glabridin, absolute configurations of (${\pm}$)-glabridin enantiomers were studied with synthetic glabridin. Synthetic glabridin enantiomers were separated by semi-preparative Sumi-chiral column chromatography, and characterized by U...

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Published inBulletin of the Korean Chemical Society Vol. 30; no. 2; pp. 415 - 418
Main Authors Kim, Mi-Hyang, Kim, Soo-Un, Kim, Yong-Ung, Han, Jae-Hong
Format Journal Article
LanguageKorean
Published 2009
Subjects
Isoflavan
Flavonoids
Glabridin
Absolute configuration
Circular dichroism (CD)
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Summary:Concerned with ambiguous stereochemistry assignment of natural (+)-glabridin, absolute configurations of (${\pm}$)-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.
Bibliography:KISTI1.1003/JNL.JAKO200902727212111
ISSN:0253-2964
1229-5949