Complete ¹H and ¹³C Resonance Assignments of Glycosidic Conjugates of Hyodeoxycholic Acid by Two-Dimensional NMR Techniques

¹H and ¹³C NMR signals were completely assigned for six 3α- and 6α-O-β-D-glycosidic conjugates (glucosides, glucuronides and N-acetylglucosaminides) of hyodeoxycholic (3α,6α-dihydroxy-5β-cholanoic) acid as their methyl ester-acetate derivatives (three being 3-glycosides and three corresponding 6-analogues). The signal assignments were performed using conventional ID NMR and several homonuclear and heteronuclear shift-correlated 2D NMR techniques (¹H-¹H COSY, ¹H-¹H NOESY, ¹H-¹H HOHAHA, ¹H-¹³C HETCOR, long-range ¹H-¹³C HETCOR). The ¹H and ¹³C signals serving to characterize each of the bile acid glycosides were identified and used in the structural elucidation of these types of biologically important compounds.