title: Stereoselective synthesis of the trisaccharide moiety of ganglioside HLG-2.
abstract: The glycan portion of ganglioside HLG-2, which was identified in the extracts of the sea cucumber Holothuria leucospilota , was synthesized in a highly efficient and stereoselective manner. The unusual sequence of the trisaccharide moiety, α-N-glycolylsialyl-(2,4)-α-N-acetylsialyl-(2,6)-glucoside, was assembled by stereoselective coupling of a 5-N,4-O-carbonyl-protected sialyl phosphate donor, a N-2,2,2-trichloroethoxycarbonyl (Troc)-protected sialyl acceptor, and a (trimethylsilyl)ethyl-β-glucosyl acceptor in high yield. The synthesis featured the high-yielding construction of two α-sialyl linkages.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs and School of Pharmaceutical Sciences, Peking University , Xue Yuan Road No. 38, Beijing 100191, China.
authors.forename: Fei-Fei
authors.initials: FF
authors.lastname: Xu
authors.forename: Yue
authors.initials: Y
authors.lastname: Wang
authors.forename: De-Cai
authors.initials: DC
authors.lastname: Xiong
authors.forename: Xin-Shan
authors.initials: XS
authors.lastname: Ye
mesh_terms: D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005732:Gangliosides / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D013237:Stereoisomerism
chemical_list: C432904:1-O-((N-glycolylneuraminosyl)-(2-4)-(N-acetylneuraminosyl)-(2-6)glucopyranosyl)ceramide; D005732:Gangliosides