Synthesis of allyl 6-O-(3-deoxy-alpha- and -beta-D-manno-oct-2- ulopyranosylonic acid)-(1----6)-2-deoxy-2-[(3R)-3-hydroxytetradecanamido]- beta-D-glucopyranoside 4-phosphate and of the copolymer of the alpha anomer with acrylamide.
The title disaccharides were synthesized by mercuric cyanide-catalyzed condensation of methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl bromide)onate and allyl 2-[(3R)-3-acetoxy-tetradecanamido]-3-O-benzyl-2-deoxy-beta-D- glucopyranoside, followed by phosphorylation of the alcoholic function of the amino sugar. The phosphorylated anomers were separated by chromatography and deprotected by conventional methods. Polymeric material was obtained by copolymerisation, catalyzed by peroxosulphate and N,N,N',N'-tetramethylethylenediamine, of the alpha anomer with acrylamide; it contained ca. one disaccharide unit for 18 acrylamide residues.
Auzanneau
F I
FI
Equipe Endotoxines du Centre National de la Recherche Scientifique, Université de Paris-Sud, France.
Mondange
M
M
Charon
D
D
Szabó
L
L
D020106:Acrylamide; D000178:Acrylamides / Q000276:immunology; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000276:immunology; D004731:Endotoxins / Q000737:chemistry; D000939:Epitopes / Q000276:immunology; D007536:Isomerism; D008070:Lipopolysaccharides / Q000737:chemistry; D008969:Molecular Sequence Data; D013403:Sugar Phosphates / Q000138:chemical synthesis* / Q000276:immunology
D000178:Acrylamides; D004187:Disaccharides; D004731:Endotoxins; D000939:Epitopes; D008070:Lipopolysaccharides; D013403:Sugar Phosphates; C076313:allyl 6-O-(3-deoxyoct-2-ulopyranosylonic acid)-(1-6)-2-deoxy-2-(3-hydroxytetradecanamido)glucopyranoside 4-phosphate; D020106:Acrylamide