Synthesis and 1H NMR characterization of the six isomeric mono-O-sulfates of 8-methoxycarbonyloct-1-yl O-beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-beta-D-glucopyran oside.

All six isomeric mono-O-sulfates of beta-D-Galp-(1-->4)-beta-D-GlcpNAc-O-(CH2)8COOMe (LacNAc-MC) have been chemically synthesized and characterized by high resolution 1H NMR spectroscopy. Sulfation causes characteristic substitution-site-specific downfield shifts of 1H NMR signals. The 4C1 chair conformation of both pyranose residues of LacNAc are unaffected by mono-O-sulfation, and, with the exception of the 3-O-sulfate derivative, glycosidic torsion angles are also unaffected.