Spectral analysis of the configuration and solution conformation of dihydrodigoxigenin epimers.
The C20 configuration and solution conformation of each epimer of dihydrodigoxigenin has been studied by circular dichroism (CD) and NMR spectroscopy. Results from the CD spectra indicate that the two epimers have opposite orientations of the beta-carbon in the lactone ring. This finding, together with X-ray crystallographic data from a separate study on the minor epimer, establishes the C20 configuration of the minor epimer as S and of the major epimer as R. NMR evidence indicates that the average lactone rotamer for the minor epimer has the C22 position located on the C12 side of the steroid nucleus, whereas the average lactone rotamer for the major epimer has the C21 position located on the C12 side of the steroid nucleus. Molecular models indicate that these are the least-hindered positions for the respective rotamers. Physical data characterizing the two epimers are provided.
D003460:Crystallization; D004076:Digoxigenin / Q000031:analogs & derivatives*; D004077:Digoxin / Q000031:analogs & derivatives*; D006868:Hydrolysis; D007783:Lactones / Q000032:analysis; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011522:Protons; D012996:Solutions; D013237:Stereoisomerism
D007783:Lactones; D011522:Protons; D012996:Solutions; C037826:20,22-dihydrodigoxigenin; D004077:Digoxin; D004076:Digoxigenin