title: Synthesis of a sialic acid alpha(2-3) galactose building block and its use in a linear synthesis of sialyl Lewis X.
abstract: [reaction: see text] The ubiquity of the sialic acid alpha(2-3) galactose linkage in oligosaccharides of biological relevance necessitates a building block for the incorporation of this motif into oligosaccharides prepared by modular synthesis. The linear synthesis of the sialyl Lewis X tumor-associated antigen (1) has been accomplished in good yield using a sialic acid alpha(2-3) galactose disaccharide building block. The disaccharide building block was synthesized efficiently from readily available galactal by a high-yielding and selective sialylation reaction.
authors.affiliation: Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zurich, 8093 Zurich, Switzerland.
authors.forename: Shinya
authors.initials: S
authors.lastname: Hanashima
authors.forename: Bastien
authors.initials: B
authors.lastname: Castagner
authors.forename: Davide
authors.initials: D
authors.lastname: Esposito
authors.forename: Toshiki
authors.initials: T
authors.lastname: Nokami
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
mesh_terms: D005690:Galactose / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D009844:Oligosaccharides / Q000737:chemistry*; D000080506:Sialyl Lewis X Antigen
chemical_list: D009844:Oligosaccharides; D000080506:Sialyl Lewis X Antigen; D019158:N-Acetylneuraminic Acid; D005690:Galactose