Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Absolute Configurations of (±)-Glabridin Enantiomers

  • Kim, Mi-Hyang (Program in Applied Life Chemistry, Department of Agricultural Biotechnology and Research Institute for Agriculture and Life Sciences, Seoul National University) ;
  • Kim, Soo-Un (Program in Applied Life Chemistry, Department of Agricultural Biotechnology and Research Institute for Agriculture and Life Sciences, Seoul National University) ;
  • Kim, Yong-Ung (Department of Herbal Pharmaceutical Engineering, Daegu Haany University) ;
  • Han, Jae-Hong (Metalloenzyme Research Group and Department of Biotechnology, Chung-Ang University)
  • Published : 2009.02.20
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Abstract

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.

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References

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