Synthesis of 2-deoxy-4-O-alpha- and -beta-D-mannopyranosyl-L-erythro-pentonic acids.
The title compounds, required for the identification of structural features of the Bordetella pertussis endotoxin, have been synthesised by condensation of benzyl 3-O-benzyl-2-deoxy-beta-L-erythro-pentopyranoside with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl bromide and with 4,6-di-O-acetyl-2,3-O-carbonyl-alpha-D-mannopyranosyl bromide, respectively, thus affording the fully protected alpha- and beta-linked disaccharides 7 and 12. Hypoiodite oxidation of the reducing disaccharides 9 and 14, obtained by conventional deprotection of 7 and 12, yielded the title compounds.
Szabó
P
P
Equipe Endotoxines du Centre National de la Recherche Scientifique (U.R.A. 1116), Université de Paris-Sud, Châtenay-Malabry, France.
Szabó
L
L
D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry; D004731:Endotoxins / Q000737:chemistry; D006090:Gram-Negative Bacteria / Q000737:chemistry; D008070:Lipopolysaccharides / Q000737:chemistry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D013400:Sugar Acids / Q000138:chemical synthesis* / Q000737:chemistry
D004187:Disaccharides; D004731:Endotoxins; D008070:Lipopolysaccharides; D013400:Sugar Acids; C073448:2-deoxy-4-O-mannopyranosyl-erythro-pentonic acid