Synthesis of a tetrasaccharide representing a minimal epitope of an arabinogalactan.
The hydrophobic alkyl chain-containing tetrasaccharide, dodecyl beta-D-galactopyranosyl-(1-->6)-beta-D-galactopyranosyl-(1-->6)-[alpha-L - arabinofuranosyl-(1-->2)]-beta-D-galactopyranoside, was synthesized efficiently using a convergent strategy. In coupling reactions, protected trichloroacetimidates proved to be better donors than their corresponding bromides in the preparation of the dodecyl disaccharide and trisaccharide. Zemplén deacylation provided the target tetramer in good overall yield.
Du
Y
Y
Research Center for Eco-Environmental Sciences, Academia Sinica, Beijing, China.
Pan
Q
Q
Kong
F
F
D002240:Carbohydrate Sequence; D002845:Chromatography; D004187:Disaccharides / Q000737:chemistry; D000939:Epitopes; D005685:Galactans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008969:Molecular Sequence Data; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000276:immunology
D004187:Disaccharides; D000939:Epitopes; D005685:Galactans; D011134:Polysaccharides; C005653:arabinogalactan