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• W2019900359 abstract "The chemical structure of the phosphorylated lipopolysaccharide (LPS) of Escherichia coli J‐5 was investigated because it is of biomedical interest in the context of septic shock, a syndrome often encountered in nosocomial infections with gram‐negative pathogens. The successive de‐ O ‐acylation and de‐ N ‐acylation of J‐5 LPS yielded phosphorylated oligosaccharides which represent the complete carbohydrate backbone. Five compounds were separated by high‐performance anion‐exchange chromatography and analysed by one‐dimensional and two‐dimensional homonuclear and heteronuclear 1 H‐NMR, 13 C‐NMR and 31 P‐NMR spectroscopy. The main product was a nonasaccharide of the structure α‐ d ‐Glc p ‐(1→3)‐[α‐ d ‐Glc p N‐(1→7)‐α‐ l , d ‐Hep p ‐(1→7)]‐α‐ l , d ‐Hep p ‐(1→3)‐α‐ l , d ‐Hep p ‐4P‐(1→5)‐[α‐Kdo p ‐(2→4)]‐α‐Kdo p ‐(2→6)‐β‐ d ‐Glc p N‐4P‐(1→6)‐α‐ d ‐Glc p N‐1P wherein all sugars are present as d ‐pyranoses. Hep and Kdo represent l glycero d manno ‐heptose and 3‐deoxy‐ d manno ‐oct‐2‐ulosonic acid, respectively. In addition, two octasaccharides and two heptasaccharides were isolated that were partial structures of the nonasaccharide. In one octasaccharide the terminal α‐ d ‐Glc p N was missing and an additional phosphate group linked to O4 of the branched heptose was present, whereas in the other octasaccharide the side‐chain Kdo was missing. In both heptasaccharides the side‐chain α‐ d ‐Glc p N‐(1→7)‐ l ‐α‐ d ‐Hep p ‐disaccharide was absent; they differed in their phosphate substitution. Whereas both heptasaccharides contained two phosphates in the lipid‐A backbone (β‐1,6‐linked Glc p N‐disaccharide at the reducing end) and one phosphate group at O4 of the first heptose, only one of them was additionally substituted with phosphate at O4 of the second heptose." @default.
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• W2019900359 date "1999-02-05" @default.
• W2019900359 modified "2023-10-17" @default.
• W2019900359 title "Isolation and structural analysis of phosphorylated oligosaccharides obtained from Escherichia coli J-5 lipopolysaccharide" @default.
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• W2019900359 doi "https://doi.org/10.1046/j.1432-1327.1999.00134.x" @default.
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