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

Autor: Akiko Kanamori, Masanori Yamaguchi, Makoto Kiso, Hideharu Ishida, Reiji Kannagi
Rok vydání: 2004
Předmět:
Zdroj: Journal of Carbohydrate Chemistry. 23:201-215
ISSN: 1532-2327
0732-8303
DOI: 10.1081/car-200030039
Popis: Synthesis and antigenic property of a novel 6‐O‐sulfated sLex 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‐glycero‐α‐D‐galacto‐2‐nonulopyranosylonate)‐(2→3)‐4,6‐di‐O‐acetyl‐2‐O‐benzoyl‐1‐thio‐β‐D‐galactopyranoside (3) with 2‐(tetradecyl)hexadecyl (2,3,4‐tri‐O‐benzyl‐α‐L‐fucopyranosyl)‐(1→3)‐2‐acetamido‐2‐deoxy‐6‐O‐4‐methoxyphenyl‐β‐D‐glucopyranoside (7) gave a protected sLex tetrasaccharide glycolipid (8). Removal of all the acyl protecting groups and subsequent lactamization afforded the lactamized sLex 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. #Synthetic Studies o...
Databáze: OpenAIRE
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