title: A first total synthesis of a novel sulfated ganglioside, 3'-O-sulfo-GM1b.
abstract: A first total synthesis of a novel sulfated ganglioside, 3'-O-sulfo-GM1b, is described. The suitably protected gangliotriose (GgOSe3) derivative, 2-(trimethylsilyl)ethyl (2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-galactopyranosyl)-(1-->4)-(2,6-di-O-benzyl-3-O-p-methoxybenzyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside was glycosylated with the alpha-NeuAc-(2-->3)-galactose donor to give the protected GM1b oligosaccharide (95%). After proper manipulation of the protecting groups, the oligosaccharide was converted into the target ganglioside by the successive introduction of the ceramide and sulfo groups, followed by complete deprotection.
authors.affiliation: Department of Applied Bio-organic Chemistry, Gifu University, Gifu 501-1193, Japan.
authors.forename: Tatsuki
authors.initials: T
authors.lastname: Komori
authors.forename: Saori
authors.initials: S
authors.lastname: Kondo
authors.forename: Hironume
authors.initials: H
authors.lastname: Ando
authors.forename: Hideharu
authors.initials: H
authors.lastname: Ishida
authors.forename: Makoto
authors.initials: M
authors.lastname: Kiso
mesh_terms: D002240:Carbohydrate Sequence; D002518:Ceramides / Q000737:chemistry; D005677:G(M1) Ganglioside / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D005732:Gangliosides / Q000138:chemical synthesis*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013431:Sulfates / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C473134:3'-O-sulfo-ganglioside M1b; D002518:Ceramides; D005732:Gangliosides; D013431:Sulfates; D005677:G(M1) Ganglioside