title: A first total synthesis of a hybrid-type ganglioside associated with amyotrophic lateral sclerosis-like disorder.
abstract: The hybrid ganglioside X1, which was identified in the bovine brain, was synthesized for the first time. Ganglioside X1 is believed to be involved in the development of amyotrophic lateral sclerosis-like disorders in patients with neurological disorders after treatment with bovine brain gangliosides. A convergent approach using two branched glycan units, the GM2-core trisaccharide and the lacto-ganglio tetrasaccharide, efficiently provided the highly branched heptasaccharide part of ganglioside X1, which was conjugated with the ceramide part to produce the protected ganglioside X1. Global deprotection delivered homogenous ganglioside X1, with which serum from the patient was reacted.
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: Akihiro
authors.initials: A
authors.lastname: Imamura
authors.forename: Nobuhiro
authors.initials: N
authors.lastname: Yuki
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; D001921:Brain / Q000378:metabolism; D002417:Cattle; D002518:Ceramides / Q000378:metabolism; D005732:Gangliosides / Q000097:blood / Q000138:chemical synthesis / Q000737:chemistry / Q000276:immunology; D006801:Humans; D009284:Naphthols; D019906:Nuclear Magnetic Resonance, Biomolecular; D014312:Trisaccharides / Q000097:blood / Q000737:chemistry
chemical_list: D002518:Ceramides; D005732:Gangliosides; D009284:Naphthols; D014312:Trisaccharides; C025917:4-chloro-1-naphthol