title: First synthesis of a pentasaccharide moiety of ganglioside GAA-7 containing unusually modified sialic acids through the use of N-Troc-sialic acid derivative as a key unit.
abstract: The pentasaccharide part of the potent neuritogenic ganglioside GAA-7 has been synthesized for the first time. The unique branched terminus constituting partially modified sialic acids and N-acetylgalactosamine was successfully established by stereoselective double-sialylation using 8-O-methyl-N-Troc-sialic acid as a donor. The final 4 + 1 coupling reaction provided a high yield of pentasaccharide, which was deprotected to deliver the target molecule.
authors.affiliation: Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan.
authors.forename: Hideki
authors.initials: H
authors.lastname: Tamai
authors.forename: Hiromune
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: D005732:Gangliosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012794:Sialic Acids / Q000737:chemistry*
chemical_list: D005732:Gangliosides; D011134:Polysaccharides; D012794:Sialic Acids; C578920:ganglioside GAA-7