Synthesis of the methyl glycosides of a tri- and a tetra-saccharide related to heparin and heparan sulphate.
The methyl glycoside of a tetrasaccharide isolated from heparin, methyl O-(alpha-L-idopyranosyluronic acid)-(1-->4)-O-(2-acetamido-2-deoxy-alpha-D- glucopyranosyl)-(1-->4)-O-(beta-D-glucopyranosyluronic acid)-(1-->3)-O-beta-D-galactopyranoside disodium salt and a trisaccharide derivative thereof, methyl O-(alpha-L-idopyranosyluronic acid)-(1-->4)-O-(2-acetamido-2- deoxy-alpha-D-glucopyranosyl)-(1-->4)-O-beta-D-glucopyranosyluronic acid disodium salt, were synthesized using a block-type strategy. A suitable protected disaccharide block of iduronic acid and glucosamine (IdoA-GlcN) was used as a key intermediate for the syntheses and was glycosidated with a protected galactose derivative and a disaccharide block of glucuronic acid and galactose (GlcA-Gal) to give tri- and tetra-saccharide derivatives, respectively. Deprotection gave the target compounds.
Nilsson
M
M
Organic Chemistry, Kabi Pharmacia AB, Stockholm, Sweden.
Svahn
C M
CM
Westman
J
J
D002240:Carbohydrate Sequence; D006031:Glycosylation; D006493:Heparin / Q000737:chemistry*; D006497:Heparan Sulfate / Q000737:chemistry; D008759:Methylglycosides / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D014312:Trisaccharides / Q000138:chemical synthesis*
D006493:Heparin; D006497:Heparan Sulfate; D008759:Methylglycosides; D009844:Oligosaccharides; D014312:Trisaccharides