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Structure elucidation and proton and carbon-13 assignment of a pentasaccharide glycoside from Agave americana

✍ Scribed by Geeta Pant; Mahesh C. Purohit; Gareth A. Morris; Adam G. W. Halstead; Robert I. G. Thompson

Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
491 KB
Volume
32
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

A glycoside extracted from the rhizomes of Agave americana was identified as 3‐O‐[{{β‐D‐xylosyl(1 → 3)}{β‐D‐xylosyl(1 → 3) ‐ β ‐ D ‐ glucopyranosyl(1 → 2)} ‐ β ‐ D ‐ glucopyranosyl(1 → 4)} ‐ β ‐ D ‐ galactopyranosyl] ‐ (25__R__) ‐ 5α ‐ spirostan‐3β‐ol by concerted use of proton and carbon‐13 2D NMR methods. Complete assignments for the sugar resonances were obtained with standard methods, but the presence of chemical shift degeneracies prevented an unequivocal determination of two of the glycosidic linkage points by the HMBC experiment. Further two‐dimensional experiments failed to resolve the ambiguity, but a clear identification of the linkages was obtained using a selective reverse INEPT experiment with homonuclear double resonance.

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