First total synthesis of ganglioside GT1a alpha.
A first total synthesis of ganglioside GT1a alpha (IV3III6II3Neu5AcGg4Cer) is described. The suitably protected sialyl alpha-(2-->6) ganglioside was glycosylated with the phenylthio glycoside of sialic acid in the presence of N-iodosuccinimide-(NIS)-trimethylsily trifluoromethanesulfonate (TMSOTf), followed by further glycosylation with the methyl thioglycoside promoted by dimethyl(methylthio)sulfonium triflate (DMTST), to give the heptasaccharide. The oligosaccharide obtained was converted into the title ganglioside by the introduction of ceramide and then complete deprotection.
Ito
H
H
Department of Applied Bioorganic Chemistry, Gifu University, Japan.
Ishida
H
H
Kiso
M
M
Hasegawa
A
A
D000954:Antigens, Surface / Q000737:chemistry; D002240:Carbohydrate Sequence; D005732:Gangliosides / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data
D000954:Antigens, Surface; D005732:Gangliosides; C084318:GT1aalpha ganglioside