title: Efficiently synthesizing lacto-ganglio-series gangliosides by using a glucosyl ceramide cassette approach: the total synthesis of ganglioside X2.
abstract: The first total synthesis of the hybrid ganglioside X2, which consisted of a highly branched octasaccharide and ceramide moieties, was accomplished by using a glucosyl ceramide cassette approach. With a disaccharyl donor, the heptasaccharide could not be constructed by glycosylation of the C4 hydroxy group of galactose at the reducing end of the pentasaccharide. In contrast, through an alternative approach with two branched glycan units, a GM2-core trisaccharide, and a lacto-ganglio tetrasaccharide, the heptasaccharyl donor could be prepared and subsequently joined with a glucosyl ceramide cassette to afford the protected ganglioside, X2. Finally, global deprotection completed the synthesis, thus affording the pure ganglioside X2.
authors.affiliation: Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan.
authors.forename: Shinya
authors.initials: S
authors.lastname: Nakashima
authors.forename: Hiromune
authors.initials: H
authors.lastname: Ando
authors.forename: Risa
authors.initials: R
authors.lastname: Saito
authors.forename: Hideki
authors.initials: H
authors.lastname: Tamai
authors.forename: Hideharu
authors.initials: H
authors.lastname: Ishida
authors.forename: Makoto
authors.initials: M
authors.lastname: Kiso
mesh_terms: D000690:Amyotrophic Lateral Sclerosis / Q000378:metabolism; D000818:Animals; D002518:Ceramides / Q000138:chemical synthesis / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000191:economics / Q000379:methods; D005732:Gangliosides / Q000138:chemical synthesis* / Q000737:chemistry; D005963:Glucosylceramides / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D002518:Ceramides; D005732:Gangliosides; D005963:Glucosylceramides; D009844:Oligosaccharides