Absolute Configurations of (¡¾)-Glabridin Enantiomers

Bulletin of the Korean chemical society

Soo Un Kim¹  Mihyang Kim¹  Jaehong Han¹  Yong ung Kim¹ 

关键词: Absolute configuration;    Circular dichroism (CD);    Flavonoids;    Glabridin;    Isoflavan;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

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.

【 授权许可】

Unknown