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.
Department of Chemistry, University of Alberta, Edmonton, Canada.
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D000606:Amino Sugars / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D005690:Galactose / Q000737:chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013463:Sulfuric Acid Esters / Q000138:chemical synthesis* / Q000737:chemistry
D000606:Amino Sugars; D004187:Disaccharides; D013463:Sulfuric Acid Esters; C000458:N-acetyllactosamine; D005690:Galactose