(13)C-N.M.R. STUDIES OF D-GLUCOSE AND D-GALACTOSE MONOSULPHATES

Article abstract of DOI:10.1016/S0008-6215(00)80847-2

D-Galactose and D-glucose 2-, 3-, 4-, and 6-sulphates, 2,3,4,6-tetra-O-acetyl-β-D-glucose 1-sulphate, and 2-acetamido-2-deoxy-D-glucose 6-sulphate have been definitively synthesised, and the positions of the sulphate groups verified by (13)C-n.m.r. spectroscopy.New syntheses are given for D-galactose 3- and 4-sulphates and for D-glucose 4-sulphate.The (13)C-n.m.r. spectra showed downfield displacements, with respect to the parent sugar, of the shifts of carbon atoms carrying a sulphate group and smaller upfield shifts for adjacent carbon atoms.The technique of deuterium-induced, differential isotope shift (d.i.s.), (13)C-n.m.r. spectroscopy is shown to be valuable for the assignment of chemical shifts.