124477-24-3Relevant academic research and scientific papers
Synthetic studies on sialoglycoconjugates 89: Synthesis of ganglioside GM3 and KDN-GM3 containing different carbon-chain length fatty acyl groups at the ceramide residue
Hasegawa, Akira,Suzuki, Naomi,Kozawa, Fumitaka,Ishida, Hideharu,Kiso, Makoto
, p. 639 - 648 (1996)
Ganglioside GM3 and KDN-ganglioside GM3, containing hexanoyl, decanoyl, and hexadecanoyl groups at the ceramide moiety have been synthesized. Selective reduction of the azido group in O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2- nonulopyranosylonate)-(2→3)-O-(2,4-di-O-acetyl-6-O-benzoyl-β-D- galactopyranosyl)-(1→4)-O-(3-O-acetyl-2,6-di-O-benzoyl-β-D- glucopyranosyl)-(1→1)-(2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (1) and O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2- nonulopyranosylonate)-(2→3)-O-(2,4-di-O-acetyl-6-O-benzoyl-β-D- galactopyranosyl)-(1→4)-O-(3-O-acetyl-2,6-di-O-benzoyl-β-D- glucopyranosyl)-(1→1)-(2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (2), coupling with hexanoic, decanoic, and hexadecanoic acids, O-deacylation, and de-esterification gave the title gangliosides GM3 (11～13) and KDN-GM3 (14～16) in good yields. On the other hand, O-deacylation of 1 and subsequent de-esterification gave 2-azido-sphingosine containing-GM3 analogue 17, which was converted into lyso-GM3, in which no fatty acyl group was substituted at the sphingosine residue, by selective reduction of the azido group.
