Synthesis of a sialic acid alpha(2-3) galactose building block and its use in a linear synthesis of sialyl Lewis X.
[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.
Hanashima
Shinya
S
Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zurich, 8093 Zurich, Switzerland.
Castagner
Bastien
B
Esposito
Davide
D
Nokami
Toshiki
T
Seeberger
Peter H
PH
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
D009844:Oligosaccharides; D000080506:Sialyl Lewis X Antigen; D019158:N-Acetylneuraminic Acid; D005690:Galactose