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Structural investigation of the lipopolysaccharide from Proteus mirabilis R45 (Re-chemotype)

Division of Biochemical Microbiology, Forschungsinstitut Borstel, Institut für Experimentelle Biologie und Medizin, Borstel, Gennany, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Universiteit Utrecht, Utrecht, The Netherlands

J.E. Thomas-Oates

Division of Biochemical Microbiology, Forschungsinstitut Borstel, Institut für Experimentelle Biologie und Medizin, Borstel, Gennany, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Universiteit Utrecht, Utrecht, The Netherlands

H. Brade

Division of Biochemical Microbiology, Forschungsinstitut Borstel, Institut für Experimentelle Biologie und Medizin, Borstel, Gennany, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Universiteit Utrecht, Utrecht, The Netherlands

O. Holst

Division of Biochemical Microbiology, Forschungsinstitut Borstel, Institut für Experimentelle Biologie und Medizin, Borstel, Gennany, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Universiteit Utrecht, Utrecht, The Netherlands

Five phosphorylated saccharides were isolated from the deacylated then N-acetylated lipopolysaccharide (LPS) of Proteus mirabilis R45 (Re-chemotype) by anion-exchange chromatography. Their structures were determined by 1- and 2-dimensional ¹H- and ³C-nuclear magnetic resonance spectroscopy as -Kdo-(2-4)-[β-L-ArapNAc-(1-8)-]--Kdo-(2-6)-β-D-GIc pNAc-(1-6)--D-GIcpNAc 1-phosphate (1), -Kdo-(2-4)-[β-L-Ara pNAc-(1-8)-]--Kdo-(2-6)-β-D-GlcpNAc-(1-6)--D-Glc pNAc 1,4'-bisphosphate (2), -Kdo-(2-4)--Kdo-(2-6)-β-D-Glc pNAc-(1-6)--D-GlcpNAc 1-phosphate (3), -Kdo-(2-4)--Kdo-(2-6)-β-D-Glc pNAc-(1-6)--D-GlcpNAc 1,4'-bisphosphate (4), and β-L-Ara pNAc 1-phosphate (5) (ArapNAc, 4-acetamido-4-deoxy-L-arabinopyranose; Kdo, 3-deoxy-D-manno-octulopyranosonic acid). Compounds 1-5 were obtained from deacylated LPS in a molar ratio of ~1.1:0.8:1.1:1.0:0.6 as determined by high-performance anion-exchange chromatography. Although we cannot exclude that in the deacylated LPS (without N-acetylation) the molar ratio may be different, the result can be taken as indication that in LPS about 50% of the 4'-phosphates of lipid A are substituted by (β-L-AraN. Furthermore, our data prove that the first Kdo in the carbohydrate chain is partially substituted by a second residue of ArapN.

The de-O-acylated LPS was additionally investigated using fast atom bombardment and B/E linked scan mass spectrometry which confirmed the above findings and also identified minor amounts of another LPS species possessing a third pentosamine residue.

Journal of Endotoxin Research, Vol. 1, No. 4, 199-206 (1994)
DOI: 10.1177/096805199400100401


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