SYNTHESIS AND H-1 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-GLUCOPYRANOSID E

摘要

All six isomeric mono-O-sulfates of beta-D-Galp-(1-->4)-beta-D-GlcpNAc-O-(CH2)(8)COOMe (LacNAc-MCO) have been chemically synthesized and characterized by high resolution (1)HNMR spectroscopy. Sulfation causes characteristic substitution-site-specific downfield shifts of H-1 NMR signals. The C-4(1) 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. [References: 34]