Gas-Liquid Chromatography of Partially Methylated Alditols as their Acetates.

Björndal, Håkan; Lindberg, Bengt; Svensson, Sigfrid; Norin, Torbjörn; Eriksson, G.; Blinc, R.; Paušak, S.; Ehrenberg, L.; Dumanović, J.

doi:10.3891/acta.chem.scand.21-1801

Cited by 343 publications

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“…Qualitative determination of monosaccharides by paper chromatography, electrophoresis and gas liquid chromatography of acetylated alditols [7] on column A were performed after acid hydrolysis with 1 M hydrochloric acid at 100 "C for 4 h followed by evaporation and drying the residue in vacuo over sodium hydroxide. Simultaneous quantitative determination of neutral monosaccharides and hexosamines was carried out according to modified procedure [8] for determination of hexosamines by gas-liquid chromatography.…”

Section: Determination Of Monosaccharide Compositionmentioning

confidence: 99%

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

et al. 1975

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On mild acid hydrolysis of lipolysaccharide from Shigella dysenteriae, type 3 the O‐specific polysaccharide (hapten) was obtained which appeared to be acidic branched hexosaminoglycan. The repeating unit of this polysaccharide represents a pentasaccharide composed of two d‐galactose residues, N‐acetyl‐d‐galactosamine, d‐glucose and unidentified acidic component. On the basis of methylation analysis, periodate oxidation, partial acid hydrolysis and chromic anhydride oxidation it is concluded that the structure of the chemical repeating unit of polysaccharide is where Glcp, is glucopyranose, Galp is galactopyranose, Galf is galactofuranose, GalNAcp is 2‐acetamido‐2‐deoxygalactopyranose and where the configuration of galactofuranoside glycosidic linkage and the structure of the acidic monosaccharide A are not known.

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Section: Determination Of Monosaccharide Compositionmentioning

confidence: 99%

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

et al. 1975

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“…The f d y methylated polysaccharide was hydrolyzed, the mixture of methylated sugars transformed into their alditol acetates and analyzed by gas liquid chromatography [25] and mass spectrometry [26]. I n order to facilitate the mass spectrometrical identifications, the reduction was performed with sodium borodeuteride in deuterium oxide.…”

Section: Methylation Analysis Of the Lipopolysaccharidesmentioning

confidence: 99%

Structural Investigations on the Core Polysaccharide of Salmonella typhimurium and the Mode of Attachment of the O-Specific Chains

1970

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Two lipopolysaccharides were analyzed comparatively : the lipopolysaccharide derived from a Salmonella typhimurium SR mutant, containing single repeating units linked to the core polysaccharide, and a lipopolysaccharide derived from a corresponding Ra mutant containing core polysaccharide only. Partial hydrolysis of these lipopolysaccharides led to the formation of a group of oligosaccharides occurring in both lipopolysaccharides. Their structural analysis provided information for the reconstruction of the hexose region of the core. From the SR lipopolysaccharide, four oligosaccharides were identified which were absent from the Ra lipopolysaccharide: (a) Man-al,4-rhamnose (derived from the repeating units) ; (b) Gal-j31,4-Glc ; (c) Gal-B1,4-(GlcNAc-a1,Z-)Glc ; (d) Gal-f?l,4-Glc-ccl,2-Gal. Oligosaccharides (b), (c), and (d) are derived from the linkage region between the repeating unit and the core. Methylation studies which were performed on the SR and Ra lipopolysaccharides led to the identification of the sugar linkages. On the basis of the present investigation, the partial structure of the SR lipopolysaccharide can be drawn as shown below, which confirms and extends previous results. The findings are discussed in regard to the biosynthesis and immunochemistry of SR and S form lipopolysaccharides. Abe-OAcGlcNAc (Glc) GalMan-ccl,4-Rha-~l,3-Gal-~l,4-Glc-al,2-Gal-ccl,3-Glc ------ Fig. 1). Glucose 11, therefore, represents a branching point ; it is substituted a t positions 2 and 4 [2], carrying N-acetylglucosamine as a small side chain (Fig. 1). The work described in this paper was performed with the aim of obtaining more information on the structure of Salmonella lipopolysaccharides, and, especially, on the linkage between 0-specific chains and the core. For this purpose, the lipopolysaccharides of two S. typhimurium mutants were compared :(a) The Ra mutant his 386, which is a deletion mutant defective in the rfb locus and which, therefore, produces a lipopolysaccharide containing, besides lipid A, only the complete core polysaccharide [3]. (b) The SR mutant SH777, which is defective in the rfc locus, and which produces a lipopolysaccharide containing the complete core, to which is attached one single 0-specific repeating unit (in contrast to the wild form lipopolysaccharide, which contains a sequence of repeating units linked to the core) [4].The analysis of oligosacchafide fragments, obtained by partial hydrolysis of the two lipopolysaccharides, as well as the results of methylation studies, confirmed the previously proposed structures of the core [5] and of the linkage region between the repeating unit and the core [2]. Furthermore, the results led to certain new details regarding sugar linkages in these lipopolysaccharides. It was found that in the SR lipopolysaccharide, the glucose I1 residue carries the N-acetylglucosamine residue a t position 2, and the terminal reducing galactose residue of the repeating unit a t position 4. Further-

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“…3 and Table 2) and gas chromatography mass spectrometry. In the gas chromatogram, two peaks were detected, and relative retention times of the corresponding alditol acetates relative to 1,5-di-O-acetyl-2,3,4,6-tetra-O-methyl glucitol were calculated and were identified by a comparison with the retention times which were previously reported by Aspinall (I) and Bjorndal et al (3). The ratio of peak areas of the two components was calculated to be 1.46: 1.00 (II :111).…”

Section: Methylation Analysis and Smith Degradationmentioning

confidence: 99%

The Klebsiella O3 Lipopolysaccharide Isolated from Culture Fluid

Hasegawa

Ohta

Mori

et al. 1983

Microbiology and Immunology

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In a series of our earlier studies, the 03 antigen isolated from culture supernatant of Klebsiella pneumoniae strain Kasuya (03:KI) (K03) was shown to exhibit very strong adjuvant activity in mice. K03 obtained was homogeneous in analyses by either gel filtration or ultracentrifugation. Its molecular weight determined by ultracentrifugal analysis was greater than 2 X 10 6 • It contained 37.9% C, 6.20% H, 0.24% N, and less than 0.1 % P. K03 was degraded into the polysaccharide moiety and lipid moiety (about 20%) by hydrolysis with I % acetic acid at 100 C for I hr. The molecular weight of the polysaccharide moiety obtained by the hydrolysis was 16,200 as determined by the Somogyi-Nelson method. Chemical analyses using methylation analysis and Smith degradation as the principal methods indicated that the polysaccharide moiety consisted of a mannan which has a pentasaccharide repeating unit of a-mannosyl-I ,3-a-mannosyl-1 ,2-a-mannosyl-1 ,2· a-mannosyl-I ,2-amannose joined through a-I,3-mannosyl linkages. The number of repetitions was less than 20. The fact that minor components such as 2-keto-3-deoxyoctonate and glucose were detected suggests the presence of a core oligosaccharide, but its precise structure is unknown.Previous studies in our laboratories have shown that the polysaccharide-rich fraction isolated from the culture supernatant of Klebsiella pneumoniae strain Kasuya (03 :Kl) exhibits a strong adjuvant effect on antibody response of mice to various antigens (12,14,15,18), and that its effect is much stronger than that of other known adjuvants including Freund's complete adjuvant and lipopolysaccharides (LPS) of Escherichia coli 0111 and 055 (12,16,17). The polysaccharide-rich fraction isolated from culture supernatant of K. pneumoniae is usually fractionated into an acidic polysaccharide (type-specific capsular antigen) and a neutral polysaccharide (13). Further studies have revealed that the substance capable of exhibiting this strong adjuvant effect is the neutral polysaccharide (13) and is serologically identical to the 03 antigen of Klebsiella (10), and that its polysaccharide moiety consists mainly of mannose (21). The 03 antigen of Klebsiella isolated from culture supernatant also exhibited a very strong adjuvant action in the induction of delayed-type hyper-683

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Gas-Liquid Chromatography of Partially Methylated Alditols as their Acetates.

Cited by 343 publications

References 0 publications

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

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

Structural Investigations on the Core Polysaccharide of Salmonella typhimurium and the Mode of Attachment of the O-Specific Chains

The Klebsiella O3 Lipopolysaccharide Isolated from Culture Fluid

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