TY - JOUR
T1 - Synthesis of simple sea cucumber ganglioside analogs
AU - Higuchi, Ryuichi
AU - Mori, Takeshi
AU - Sugata, Tetsuji
AU - Yamada, Koji
AU - Miyamoto, Tomofumi
PY - 1999/11
Y1 - 1999/11
N2 - Two simple sea cucumber ganglioside analogs 8 (NeuAcα2→6 Glcβ 1→1 docosanol) and 9 (NeuAcβ2→6 Glcβ 1→1 docosanol), containing a long-chain alcohol as a mimic of ceramide, have been synthesized. Coupling of the methyl 2-thioglycoside derivative of N-acetylneuraminic acid S with docosyl glucoside derivative 3 afforded the protected ganglioside analogs 6 and 7, which were deprotected to give the corresponding ganglioside analogs 8 and 9, respectively. The 13C-NMR data obtained for these anomers 8 and 9 should prove useful for the determination of anomeric configurations of sialic acid residues in gangliosides.
AB - Two simple sea cucumber ganglioside analogs 8 (NeuAcα2→6 Glcβ 1→1 docosanol) and 9 (NeuAcβ2→6 Glcβ 1→1 docosanol), containing a long-chain alcohol as a mimic of ceramide, have been synthesized. Coupling of the methyl 2-thioglycoside derivative of N-acetylneuraminic acid S with docosyl glucoside derivative 3 afforded the protected ganglioside analogs 6 and 7, which were deprotected to give the corresponding ganglioside analogs 8 and 9, respectively. The 13C-NMR data obtained for these anomers 8 and 9 should prove useful for the determination of anomeric configurations of sialic acid residues in gangliosides.
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U2 - 10.1002/(sici)1099-0690(199911)1999:11<3175::aid-ejoc3175>3.0.co;2-o
DO - 10.1002/(sici)1099-0690(199911)1999:11<3175::aid-ejoc3175>3.0.co;2-o
M3 - Article
AN - SCOPUS:0032698889
SP - 3175
EP - 3178
JO - Justus Liebigs Annalen der Chemie
JF - Justus Liebigs Annalen der Chemie
SN - 1434-193X
IS - 11
ER -