Two-dimensional 1H-N.M.R. studies of cello-oligosaccharides: The utility of multiple-relay chemical-shift-correlated spectroscopy

doi:10.1016/0008-6215(87)80159-3

Carbohydrate Research

Volume 163, Issue 1, 1 June 1987, Pages 1-8

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Abstract

500-MHz, ¹H-n.m.r. spectra of cello-oligosaccharides were studied. The resonance assignments for cellotriose were made by combined use of multiple-relayed, coherence-transfer chemical-shift-correlated spectroscopy (multiple-RELAY-COSY). Spectra of a mixture of the α and β anomers of d-glucose were completely separated into the respective spectra by four-fold-RELAY-COSY. Resonance assignments for cellulose were made on the basis of the results for cello-oligosaccharides.

References (16)

B. Capon et al.
Carbohydr. Res.
(1979)
J.C. Gast et al.
Carbohydr. Res.
(1980)
P.H. Bolton
J. Magn. Reson.
(1982)
A. Bax et al.
J. Magn. Reson.
(1985)
A. Bax et al.
J. Magn. Reson.
(1981)
K. Nagayama et al.
Biochem. Biophys. Res. Commun.
(1977)
L. Braunschweiler et al.
J. Magn. Reson.
(1983)
A. Heyraud et al.
Biopolymers
(1979)

There are more references available in the full text version of this article.

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Two-dimensional 1H-N.M.R. studies of cello-oligosaccharides: The utility of multiple-relay chemical-shift-correlated spectroscopy

Abstract

Carbohydr. Res.

Carbohydr. Res.

J. Magn. Reson.

J. Magn. Reson.

J. Magn. Reson.

Biochem. Biophys. Res. Commun.

J. Magn. Reson.

Biopolymers

Two-dimensional ¹H-N.M.R. studies of cello-oligosaccharides: The utility of multiple-relay chemical-shift-correlated spectroscopy