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Complete 1 H and 13 C Resonance Assignments of Glycosidic Conjugates of Hyodeoxycholic Acid by Two‐Dimensional NMR Techniques
Author(s) -
Momose Toshiaki,
Iida Takashi,
Mushiake Kumiko,
Goto Junichi,
Nambara Toshio
Publication year - 1996
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199609)34:9<681::aid-omr952>3.0.co;2-q
Subject(s) - chemistry , heteronuclear molecule , glycosidic bond , two dimensional nuclear magnetic resonance spectroscopy , homonuclear molecule , glycoside , stereochemistry , proton nmr , carbon 13 nmr , nuclear overhauser effect , nuclear magnetic resonance spectroscopy , organic chemistry , molecule , enzyme
1 H and 13 C 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 1D NMR and several homonuclear and heteronuclear shift‐correlated 2D NMR techniques ( 1 H– 1 H COSY, 1 H– 1 H NOESY, 1 H– 1 H HOHAHA, 1 H– 13 C HETCOR, long‐range 1 H– 13 C HETCOR). The 1 H and 13 C 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.