Somatic Antigen of Shigella dysenteriae Type 3. Structural Features of Specific Polysaccharide Chain

Dmitriev, Boris A.; Backinowsky, Leon V.; Львов, В Л; Kochetkov, Nikolay K.; Hofman, Irihna L.

doi:10.1111/j.1432-1033.1975.tb09894.x

Cited by 60 publications

(31 citation statements)

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“…Paper chromatography and paper electrophoresis followiiig acid hydrolysis showed that the polysaccharide from E. coli 0124 consisted of glucose, galactose, galactosamine and an acidic component which had the same chromatographic mobility as the acidic coniponent found in Sh. dysenteriae type 3 [6]. The latter has recently been identified as 4-0-(1-carboxyethyl)-D-glucopyranose (glucolactilic acid) [7].…”

Section: Isolation and Characterization Of The 0-specific Polj~sacchamentioning

confidence: 99%

“…In paper electrophoresis [6] The proton magnetic resonance spectrum of polysaccharide 11, recorded at I00 MHz (Fig. 3) exhibited signals of the C-methyl group of glucolactilic acid (6 = 1.4 ppm; 3 protons; J = 6 Hz; doublet), of the acetamido group of N-acetylgalactosamine (6 = 2.05 ppm; 3 protons; singlet) and five signals corresponding to five anomeric protons (4.40,4.50,4.76 ppm, doublet; J = 6 Hz; 4.94 ppm, doublet, J = 3 Hz; 5.06 ppm).…”

Section: Physical Characterizationmentioning

confidence: 99%

“…Isolation of oligosaccharides by elution from Dowex 1x8 resin with a gradient of acetic acid and analysis of the individual oligosaccharides by sugar analysis, methylation analysis and oxidation with bromine was described previously [6].…”

Section: Partial Hydrolysis Of the Polysaccharide And Identification mentioning

confidence: 99%

“…Gas chromatography mass spectrometry was performed on a Varian MAT Gnom 11 1 instrument with columns A and B [6].…”

Section: Methylation Analysismentioning

confidence: 99%

“…E. coli 0124 is known to cross react with Shigellu dysenferiue type 3 [1,5]. The structure of type 3 lipopolysaccharide was elucidated recently [6]. It was found to contain 4-0-( 1 -carboxyethyl)-D-glucopyranose (glucolactilic acid), a new type of carbohydrate component [7].…”

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Cell-Wall Lipopolysaccharide of the 'Shigella-Like' Escherichia coli 0124. Structure of the Polysaccharide Chain

et al. 1976

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From Escherichiu coli 0124 two lipopolysaccharide preparations were obtained with phenol/water extraction and cetavlon precipitation. Polyacrylamide gel electrophoresis in the presence of sodium dodecylsulfate and chemical analysis showed that the two preparations differed only in the extent of the 0-specific polysaccharide moiety. In passive haemagglutination and gel precipitation the two lipopolysaccharide preparations from E. coli 0124 and the corresponding preparations from Shigellu dysenteriur type 3 reacted alike.The 0-specific polysaccharide moiety was characterized with proton magnetic resonance spectroscopy, optical rotation and paper electrophoresis. The constituents were determined by gas chromatography and ion-exchange chromatography. The polysaccharide contained glucose (Glc), galactose (Gal), galactosamine (GalN) and 4-0-( 1 '-carboxyethy1)-D-glucopyranose (glucolactilic acid, GlcLA) in the molar ratios of 1 : 2: 1 : 1. Glucolactilic acid, which has a structure similar to muramic acid, was first found in Sh. dysenteriue. The polysaccharide from E. coli 0124 and oligosaccharides obtained from it by partial acid hydrolysis were subjected to methylation analysis using the method of combined gas chromatography-mass spectrometry. The results indicated that the pentasaccharide repeating unit of the polysaccharide is GlcLA 1-14, Glc

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Section: Isolation and Characterization Of The 0-specific Polj~sacchamentioning

confidence: 99%

Section: Physical Characterizationmentioning

confidence: 99%

Section: Partial Hydrolysis Of the Polysaccharide And Identification mentioning

confidence: 99%

“…Gas chromatography mass spectrometry was performed on a Varian MAT Gnom 11 1 instrument with columns A and B [6].…”

Section: Methylation Analysismentioning

confidence: 99%

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Cell-Wall Lipopolysaccharide of the 'Shigella-Like' Escherichia coli 0124. Structure of the Polysaccharide Chain

et al. 1976

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Bausteine von Oligosacchariden, XXXII. Synthese der verzweigten Pentasaccharid‐Einheit der O‐spezifischen Seitenkette des Lipopolysaccharides von Shigella Dysenteriae

Paulsen

Bünsch

1981

Chem. Ber.

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Die verzweigte Pentasaccharid-Sequenz 43, welche die repeating-unit der 0-spezifischen Seitenkette des Lipopolysaccharides von Shigella Dysenteriae der Serotype zwei darstellt, wurde synthetisiert. Dabei wird ein Trisaccharidhalogenid-Block aus drei 2-Azido-Zuckern rnit einem Disaccharid-Block zum Pentasaccharid verkniipft. Bei allen Verkniipfungsschritten werden stereoselektiv a-glycosidische Bindungen hergestellt. Das Azidverfahren, unsere Leitlinien zur a-Glycosidsynthese und die Halogenierungsmethode rnit Titantetrabrornid haben hierbei ihre Leistungsfahigkeit bewiesen. Building Units for Oligosaccharides, XXXIll) Synthesis of the Branched Pentasaccharide Unit of the 0-Specific Side Chain of the Lipopolysaccharide Obtained from Shigelh DysenteriaeThe branched pentasaccharide sequence 43 was synthesized. This is the repeating-unit of the 0-specific side chain belonging to the lipopolysaccharide obtained from Shigella Dysenteriae of serotype two. A trisaccharide halide block, obtained from three 2-azido-sugars, was combined with a disaccharide block to give the pentasaccharide. Each combination step of the synthesis gave a-glycosides stereoselectively. The efficiencies of the azide procedure, our routes to a-glycosides and the titanium tetrabromide halogenation method are shown here.Die gramnegativen Shigellu-Bakterien sind Erreger der Ruhr. Die auf ihrer Oberflache lokalisierten Lipopolysaccharide sind sehr wirksame Endotoxine. Serologisch unterteilt man die Shigellen in vier Subgruppen. Von der hier betrachteten Gruppe Shigella Dysenteriae sind bisher 10 Serotypen bekannt2).Die Struktur der Lipopolysaccharide der Shigellen ist denen der Salmonellen im Lipid-A-Teil und irn Kernpolysaccharid-Teil ahnlich3a4). Stark unterschiedlich sind dagegen die 0-spezifischen Seitenketten. Diese nach auRen stehenden Teile des Lipopolysaccharides sind jedoch die irnmundominanten Strukturen, die als Antigene die Bildung der gegen das Bakterium gerichteten Antikorper im Saugetierorganismus stimulieren konnen. Der Strukturaufklarung der 0-spezifischen Seitenkette und ihrer Synthese kornmt somit besondere Bedeutung zu. Durch Synthese ihrer Strukturen kame man zu synthetischen bakterienfreien Antigenen, die zu einer spezifischen Immunisierung geeignet sein sollten.

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Specific polysaccharides of the lipopolysaccharides of Gram-negative bacteria

Komandrova¹,

Gorshkova²,

Ovodov³

1986

Chem Nat Compd

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Somatic Antigen of Shigella dysenteriae Type 3. Structural Features of Specific Polysaccharide Chain

Cited by 60 publications

References 13 publications

Cell-Wall Lipopolysaccharide of the 'Shigella-Like' Escherichia coli 0124. Structure of the Polysaccharide Chain

Cell-Wall Lipopolysaccharide of the 'Shigella-Like' Escherichia coli 0124. Structure of the Polysaccharide Chain

Bausteine von Oligosacchariden, XXXII. Synthese der verzweigten Pentasaccharid‐Einheit der O‐spezifischen Seitenkette des Lipopolysaccharides von Shigella Dysenteriae

Specific polysaccharides of the lipopolysaccharides of Gram-negative bacteria

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