Synthesis and Antigenic Property of a Novel Sialyl 6-O-Sulfo Lewis X Neo-glycolipid Containing Lactamized Neuraminic Acid

摘要

Synthesis and antigenic property of a novel 6-O-sulfated sLe~x neo-glycolipid containing lactamized neuraminic acid are described. Coupling of methyl (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-g/ycero-alpha-D-galacto-2-nonulopyr-anosylonate)-(2 → 3)-4,6-di-O-acetyl-2-O-benzoyl-l-thio-beta-D-galactopyranoside (3) with 2-(tetradecyl)hexadecyl (2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-(l → 3)-2-acet-amido-2-deoxy-6-O-4-methoxyphenyl-beta-D-glucopyranoside (7) gave a protected sLe~x tetrasaccharide glycolipid (8). Removal of all the acyl protecting groups and subsequent lactamization afforded the lactamized sLe~x derivative(10), which was converted to the target compound (14) by selective removal of the 4-methoxyphenyl group and 6-O-sulfation of the GlcNAc residue, and removal of all protective groups under the basic conditions furnished the target molecule. The antigenic property of the synthesized neo-glycolipid was examined by TLC-immunostaining with G159 monoclonal antibody.