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Lipopolysaccharides from Serratia marcescens Possess One or Two 4‐Amino‐4‐deoxy‐ L ‐arabinopyranose 1‐Phosphate Residues in the Lipid A and D ‐ glycero ‐ D ‐ talo ‐Oct‐2‐ulopyranosonic Acid in the Inner Core Region
Author(s) -
Vinogradov Evgeny,
Lindner Buko,
Seltmann Guntram,
RadziejewskaLebrecht Joanna,
Holst Otto
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600186
Subject(s) - lipid a , chemistry , muramic acid , serratia marcescens , hydrolysis , acylation , acetic acid , electrospray ionization , nuclear magnetic resonance spectroscopy , mass spectrometry , acetic anhydride , strain (injury) , oligosaccharide , chromatography , stereochemistry , biochemistry , cell wall , bacteria , peptidoglycan , biology , genetics , escherichia coli , anatomy , gene , catalysis
The carbohydrate backbones of the core‐lipid A region were characterized from the lipopolysaccharides (LPSs) of Serratia marcescens strains 111R (a rough mutant strain of serotype O29) and IFO 3735 (a smooth strain not serologically characterized but possessing the O‐chain structure of serotype O19). The LPSs were degraded either by mild hydrazinolysis (de‐ O ‐acylation) and hot 4 M KOH (de‐ N ‐acylation), or by hydrolysis in 2 % aqueous acetic acid, or by deamination. Oligosaccharide phosphates were isolated by high‐performance anion‐exchange chromatography. Through the use of compositional analysis, electrospray ionization Fourier transform mass spectrometry, and 1 H and 13 C NMR spectroscopy applying various one‐ and two‐dimensional experiments, we identified the structures of the carbohydrate backbones that contained D ‐ glycero ‐ D ‐ talo ‐oct‐2‐ulopyranosonic acid and 4‐amino‐4‐deoxy‐ L ‐arabinose 1‐phosphate residues. We also identified some truncated structures for both strains. All sugars were D ‐configured pyranoses and α‐linked, except where stated otherwise.