The crystal structure of 18-alpha-glycyrrhetinic acid (trans junction of the D/E rings) has been determined in order to compare its stereochemical features with those of the known 18-beta form (cis junction of the D/E rings). The two stereoisomers exhibit different physiological actions. A comparison of their common moieties shows significant differences between the conformations of the unsaturated C ring, with some torsion angles differing by more than ten degrees. Further differences involve the convexity of the ABCD region, which in the alpha-form is smaller than that observed in the beta-isomer, and smaller than that reported for the mean steroid configuration.
The crystal structure of 18α-glycyrrhetinic acid (trans junction of the D/E rings) has been determined in order to compare its stereochemical features with those of the known 18β form (cis junction of the D/E rings). The two stereoisomers exhibit different physiological actions. A comparison of their common moieties shows significant differences between the conformations of the unsaturated C ring, with some torsion angles differing by more than ten degrees. Further differences involve the convexity of the ABCD region, which in the α form is smaller than that observed in the β isomer, and smaller than that reported for the mean steroid configuration.
Crystal and molecular structure of 18α-glycyrrhetinic acid / Antolini, L; Vampa, G; Benvenuti, Stefania; Pecorari, P.. - In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS II. - ISSN 0300-9580. - STAMPA. - 1:1(1992), pp. 65-67. [10.1039/P29920000065]
Crystal and molecular structure of 18α-glycyrrhetinic acid
BENVENUTI, Stefania;
1992
Abstract
The crystal structure of 18α-glycyrrhetinic acid (trans junction of the D/E rings) has been determined in order to compare its stereochemical features with those of the known 18β form (cis junction of the D/E rings). The two stereoisomers exhibit different physiological actions. A comparison of their common moieties shows significant differences between the conformations of the unsaturated C ring, with some torsion angles differing by more than ten degrees. Further differences involve the convexity of the ABCD region, which in the α form is smaller than that observed in the β isomer, and smaller than that reported for the mean steroid configuration.
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