Configuration of the acetal carbon atom of pyruvic acid acetals in some bacterial polysaccharides

Garegg, Per J.; Jansson, Per‐Erik; Lindberg, Bengt; Lindh, Frank; Lōnngren, Jörgen; Kvarnström, Ingemar; Nimmich, Wolfgang

doi:10.1016/s0008-6215(00)83666-6

Cited by 152 publications

(38 citation statements)

References 23 publications

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“…Garegg et al (58) have recently determined the orientation of the 3,4-and 4,6-pyruvylated-oGal in various Klebsiella polysaccharides by nuclear magnetic resonance measurements. K30 and K33 with 3,4 pyruvate are both in the S configuration, whereas K21 and Rhizobium trifolii U226 with 4,6 pyruvate were in the R form; however, in the 4,6 polysaccharides, the orientation of the methyl group was equatorial and in the 3,4 compounds was endo relative to the acetal ring so that they all have the same conformation despite the different linkage.…”

Section: Discussionmentioning

confidence: 99%

“…It is of significance that all of the pyruvylated polysaccharides that reacted with IgM wzA and IgM M^v are known to have the methyl group of the pyruvate moiety equatorial and the carboxyl group axial to the plane of the acetal ring (58) and that this is also the orientation in the R forms of methyl 4,6pyDGala and 4,6pyDGalfl. Thus, the precipitation and inhibition involve the same spatial relationships of the determinant and inhibitors.…”

Section: Discussionmentioning

confidence: 99%

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Human monoclonal macroglobulins with specificity for Klebsiella K polysaccharides that contain 3,4-pyruvylated-D-galactose and 4,6-pyruvylated-D-galactose.

Kabat¹,

Liao²,

Bretting³

et al. 1980

The Journal of Experimental Medicine

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Two human IgM myeloma proteins, IgMWEA and IgMMAY, were found to react with agar and Klebsiella polysaccharides that contain pyruvylated D-galactose (DGal). Quantitative precipitin data and precipitin inhibition studies with methyl alpha- and beta-glycosides of 4,6-pyruvylated-D-galactose showed their combining sites to be different, although each was directed against the pyruvylated-D-Gal, one reacting most specifically with Klebsiella polysaccharides with terminal nonreducing beta-linked 2,4 pyruvylated-D-Gal, whereas the other reacted equally well with Klebsiella polysaccharides that contain 3,4 beta-linked and 4,6 alpha-linked terminal nonreducing pyruvylated-DGal. Inhibition studies showed that both sites are directed toward one of the two space isomers of 3,4- or 4,6-pyruvylated DGal, the form in which the methyl group of the pyruvate is equatorial, or endo, and its carboxyl group axial, or exo, to the plane of the acetal ring. Coprecipitation studies showed the combining site of IgMWEA to be located on an (Fab')2 fragment and not on the (Fc)5mu fragment. The monoclonal peak in the serum of IgMMAY was specifically precipitated by Klebsiella polysaccharide. Myeloma proteins with specificities of this type may occur with reasonable frequency in humans and may be a consequence of clonal expansion from inapparent infection, carrier states, or disease produced by various Klebsiella organisms.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Human monoclonal macroglobulins with specificity for Klebsiella K polysaccharides that contain 3,4-pyruvylated-D-galactose and 4,6-pyruvylated-D-galactose.

Kabat¹,

Liao²,

Bretting³

et al. 1980

The Journal of Experimental Medicine

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“…3A). The chemical shift of 1.439 ppm of the acetal methyl group shows that the configuration at the acetal carbon atom is in the S-form in FGL-V [14]. (Fig.…”

Section: Carbohydrate Composition Of the Acid Methanolysates Of Fgl-vmentioning

confidence: 96%

Novel phosphonoglycosphingolipids containing pyruvylated galactose from the nervous system of Aplysia kurodai

Araki

Abe

Satake

et al. 1991

European Journal of Biochemistry

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We have now isolated two other pyruvylated galactose-containing phosphonoglycosphingolipids, named FGL-V and FGL-IIa, from the nervous tissue of Aplysiu, and characterized them as [3,4-O-(S-l -carboxyethy1idene)lGalPl + 3GalNAcal --f 3[6'-0-(2-arninoethylphosphonyl)Galal + 21 (2-aminoethylphosphonyl + 6) GalBl + 4GlcP1 + 1 ceramide and [3,4,O-(S-1 -carboxyethylidene)]Gal/?l + 3GalNAc a1 + 3[6'-0-(2-aminoethylphosphony1)Galal 4 2lGalPI + 4Glcfi11 + ceramide, respectively.Their major aliphatic components are palmitic acid, octadeca-4-sphingenine and anteisononadeca-4-sphingenine.Thus, the nervous system of Aplysiu contains several pyruvylated phosphonoglycolipids.The marine mollusc Aplysia has been used successfully in studies on the cellular and molecular processes of neuronal functions.We have found a new family of phosphonoglycosphingolipids in the tissues of Aplysiu. Of these, six predominant glycolipids, tentatively named FGL-I, FGL-IIa, FGL-lib, FGL-V, F-9 and F-21, were found only in the nervous systemWe have reported the isolation of FGL-IIb and its characterization as [3,4-0-(1-carboxyethylidene)]Gal~1 + 3GalNAcal + 3(Fucal -+ 2)(2-aminoethylphosphonyl + 6). Antiserum raised against FGL-IIb reacted not only with FGL-IIb, but also with FGL-I, FGL-IIa, FGL-V and F-9 on thin-layer immunostaining [2]. These glycolipids seemed to have a pyruvic acid residue linked to galactose at their nonreducing end, because the immunochemical study suggested that the carboxyl group of pyruvic acid linked to the terminal galactose of FGL-IIb was an essential epitope for the binding of the antibody [3].In the present paper, we determined the structures of two related phosphonoglycosphingolipids, FGL-V and FGL-IIa, isolated from the nervous tissue of Aplysiu. EXPERIMENTAL PROCEDURES Fractionation and purijkation of glycolipids FGL-V and FGL-IIaTotal glycolipids (927 mg) were prepared from an acetone powder (100 g) of the nervous tissue (1 kg) of Aplysiu as Correspondence to S. Araki, Department of Neurochemistry, Brain Research Institute, Niigata University, Asahimachi 1, Niigata, Japan 951Abbreviations. 2-AEP, 2-aminoethylphosphonate; FAB-MS, fastatom-bombardment mass spectrometry; COSY, chemical-shift-correlated spectroscopy. described previously [4]. FGL-V and FGL-IIa were purified further by successive chromatography on an Iatrobeads column. The total glycolipid fraction (1 50 mg/run) was dissolved in 2 ml chloroform/methanol/water (60: 35 : 8, by vol.) and applied to a column of Iatrobeads (6RS-8060, Iatron Lab., Tokyo; 1.6 x 36.5 cm). Glycolipids were eluted with a discontinuous gradient of chloroform/methanol/water as described previously [4] and monitored by high-performance TLC using 1-propanol/concentrated ammonium hydroxide/ water (75 : 5 : 25, by vol.). Three glycolipid fractions were obtained by column chromatography. The third one, containing FGL-V, was re-chromatographed on another Iatrobeads column (1 .O x 45 cm) using 300 ml of a linear gradient of 1-propanol/concentrated ammonium hydroxidelwater (75 : 5 : 20 ...

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“…Spectra were recorded at 90 MHz and 335 K for de-0-acylated LPS (LPS,,,,) and the polysaccharide (PS), and at The 'H-NMR and "C-NMR spectra of de-0-acylated LPS were assigned using 'H,'H-correlation spectroscopy (COSY), COSY with one-step coherence transfer (COSY RCT), and 'H,"C-heteronuclear COSY methods (Figs 1 A and 2A, Tables 1 and 2). The spectra corresponded to a polymer with a tetrasaccharide repeating unit containing two N-acetylated amino sugars ("C-NMR, the signals of amino-group bearing carbon atoms at 52.5 ppm and 54.9 ppm, N-acetyl group signals at 23.3, 23.7, 174.8, and 175.0 ppm), one hexuronic acid (carboxyl group signal at 175.5 ppm), one hexose, and one pyruvate residue, the absolute configuration of which was ( R ) as shown by 6, (26.1 ppm) of its methyl group [18]. The vicinal proton coupling constants of the monosaccharide residues corresponded to two b-gluco-(GlcA residue A and GlcNAc residue C) and two bgalactopyranosides (Gal residue D and GalNAc residue B, see formula).…”

Section: Resultsmentioning

confidence: 98%

Structural and Serological Characterisation of the O‐Specific Polysaccharide from Lipopolysaccharide of Acinetobacter calcoaceticus Strain 7 (DNA Group 1)

Vinogradov

Pantophlet

Haseley

et al. 1997

European Journal of Biochemistry

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S‐form lipopolysaccharide was isolated by phenol/water extraction from a strain of Acinetobacter calcoaceticus (DNA group 1). The structure of the O‐antigenic polysaccharide was determined by compositional analysis and NMR spectroscopy of the de‐O‐acylated lipopolysaccharide. The isolated polysaccharide obtained after hydrolysis of lipopolysaccharide in 0.01 M trifluoroacetic acid has the following structure: in which Pyr is pyruvate. The O‐acetyl substitution of D‐Gal was non‐stoichiometric. The O‐antigen was specifically recognised in western blots by polyclonal rabbit antisera.

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Configuration of the acetal carbon atom of pyruvic acid acetals in some bacterial polysaccharides

Cited by 152 publications

References 23 publications

Human monoclonal macroglobulins with specificity for Klebsiella K polysaccharides that contain 3,4-pyruvylated-D-galactose and 4,6-pyruvylated-D-galactose.

Human monoclonal macroglobulins with specificity for Klebsiella K polysaccharides that contain 3,4-pyruvylated-D-galactose and 4,6-pyruvylated-D-galactose.

Novel phosphonoglycosphingolipids containing pyruvylated galactose from the nervous system of Aplysia kurodai

Structural and Serological Characterisation of the O‐Specific Polysaccharide from Lipopolysaccharide of Acinetobacter calcoaceticus Strain 7 (DNA Group 1)

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