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1 H and 13 C NMR analysis of D ‐amygdalin: Oligosaccharide assignment and sequencing
Author(s) -
Ribeiro Anthony A.
Publication year - 1990
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/mrc.1260280907
Subject(s) - chemistry , amygdalin , disaccharide , chemical shift , oligosaccharide , nuclear magnetic resonance spectroscopy , two dimensional nuclear magnetic resonance spectroscopy , coupling constant , proton nmr , monosaccharide , nmr spectra database , crystallography , spectral line , analytical chemistry (journal) , stereochemistry , organic chemistry , physics , medicine , alternative medicine , pathology , particle physics , astronomy
The 1 H and 13 C NMR spectra of D‐amygdalin, a cyanogenetic disaccharide accumulated in food plants, were assigned using a combination of NMR techniques. Methods applied include standard 1 H– 1 H COSY, proton zero quantum coherence (ZQCOSY), 1D NOE, broad‐band decoupled 1 H– 13 C chemical shift correlation and long‐range 1 H– 13 C chemical shift correlation. ZQCOSY was especially useful in assigning the closely spaced sugar resonances, and long‐range 1 H‐ 13 C chemical shift correlation allowed sequencing of the monosaccharide rings. Coupling constants useful in conformational analysis are derived from highly digitized 1 H 1D spectra and 2D J ‐resolved spectroscopy. The 1 H and 13 C chemical shifts and coupling constants indicate that the β‐D‐glucopyranose rings of D‐amygdalin adopt a 4 C 1 chair conformation.