Solvent dependence of the rotamer population around the interglycosidic C(5)-C(6) bond of (1 ® 6)-b-linked digalactopyranosides

N.K. Vries, de, H.M. Buck

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Abstract

A 300-MHz 1H NMR study of the rotamer population around the interglycosidic C(5)C(6) bond of methyl 2,3,4-tri-O-methyl-6-O-(2,3,4,6-tetra-O-acetyl-ß-D-galactopyranosyl)-ß- (1) and --D-galactopyranoside (2) is reported. The existence of the (1¿6)-ß-linkage in these compounds is established by homo- and heteronuclear 2-D NMR techniques. It is shown that the dependence on solvent polarity of the population around the C(5)C(6) bond for the dissaccharides is almost identical to that for monosaccharides. The influences of stereoelectronic effects and solute–solvent interactions on the conformational properties of the interglycosidic linkage are discussed briefly.
Original languageEnglish
Pages (from-to)453-460
Number of pages8
JournalRecueil des Travaux Chimiques des Pays-Bas
Volume106
Issue number8
DOIs
Publication statusPublished - 1987

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