Synthesis of novel ganglioside GM4 analogues containing N-deacetylated and lactamized sialic acid: probes for searching new ligand structures for human L-selectin.
Novel ganglioside GM4 analogues, which contain N-deacetylated or lactamized sialic acid instead of usual N-acetylneuraminic acid, were synthesized in a highly efficient manner. (Methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-alpha-D-galacto-2-nonulopyranosylonate)-(2-->3)-4,6-di-O-acetyl-2-O-benzoyl-D-galactopyranosyl trichloroacetimidate was coupled with 2-(tetradecyl)hexadecanol to give the desired beta-glycoside in high yield. Successive O- and N-deacylation, and saponification of the methyl ester group afforded the N-deacetylated sialyl derivative that was converted by treatment with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in Me2SO into the lactamized sialic acid-containing ganglioside GM4 analogue.
Otsubo
N
N
Department of Applied Bioorganic Chemistry, Gifu University, Japan.
Ishida
H
H
Kiso
M
M
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005732:Gangliosides / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D019041:L-Selectin / Q000737:chemistry; D007769:Lactams / Q000737:chemistry; D008024:Ligands; D015335:Molecular Probes / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D019158:N-Acetylneuraminic Acid / Q000737:chemistry; D009438:Neuraminic Acids / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular
D005732:Gangliosides; D007769:Lactams; D008024:Ligands; D015335:Molecular Probes; D009438:Neuraminic Acids; D019041:L-Selectin; C028253:ganglioside, GM4; D019158:N-Acetylneuraminic Acid