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1H and 13C NMR analysis of D-amygdalin: Oligosaccharide assignment and sequencing

✍ Scribed by Anthony A. Ribeiro

Book ID
102951447
Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
683 KB
Volume
28
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

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.

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