Preferred Conformation about the C5-C6 Bond of N-Acetylneuraminyl(2-6)-D-galacto- and D-glucopyranosides in Solution

Article abstract of DOI:10.1021/jo00005a015

Diastereoselective deuteration and 1H NMR spectroscopy were applied in a conformational study of the C5-C6 bond in four stereoisomeric methyl N-acetylneuraminyl(2-6)-β-D-hexopyranosides .In aqueous solution, NeuNAcα(2-6)Gal prefers a gt conformer (gg:gt:tg = ca. 20:60:20), NeuNAc(2-6)Glc isomers prefer a gg (gg:gt:tg = 60:40:0), and NeuNAcβ(2-6)Gal exists equally in the three conformers.