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Synthesis and 1H NMR characterization of the six isomeric mono-O-sulfates of 8-methoxycarbonyloct-1-yl O-β-d-galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-β-d-glucopyranoside

✍ Scribed by Robert A. Field; Albin Otter; Wenyi Fu; Ole Hindsgaul

Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
831 KB
Volume
276
Category
Article
ISSN
0008-6215

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✦ Synopsis

All six isomeric mono-O-sulfates of fl-D-Galp-(1-~4)-fl-D-GlcpNAc-O-(CH2)sCOOMe (LacNAc-MCO) have been chemically synthesized and characterized by high resolution 1H NMR spectroscopy. Sulfation causes characteristic substitution-site-specific downfield shifts of I H NMR signals. The 4C 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.

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