Branched Monosialo Gangliosides of the Lacto-Series Isolated from Bovine Erythrocytes: Characterization of a Novel Ganglioside, NeuGc-Isooctaosylceramide

Dasgupta, Somsankar; Hogan, Edward L.; Glushka, John; Vanhalbeek, H.

doi:10.1006/abbi.1994.1181

Cited by 16 publications

(10 citation statements)

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“…Two additional ␣-anomeric signals were observed with respect to QN.1 in the NMR spectrum recorded at 300 K (data not shown) at ␦ 4.912 and 5.146. The resonance at ␦ 4.912 corresponded to H-1 of Man-B (28), and the signal at ␦ 5.146 originated from H-1 of the Hex(␣1-)Gal structure (32,33). In the TOCSY spectrum (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…The non-sulfated analog has been found on the N-linked glycans of mouse oocyte ZP3 (60), porcine thyroglobulin (31), and IgG1 antibodies produced by murine and transfectoma cell subclones (61) and has also been observed on gangliosides (33). The Gal(␣1-3) linkage to the reducing terminal GalNAc in O-linked glycans was found to be present in significant quantities only in brain (62) and nervous tissue glycoproteins (63).…”

Section: Characterization Of N-glycans Of Bovine Peripheral Myelin P0mentioning

confidence: 99%

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Epitope Diversity of N-Glycans from Bovine Peripheral Myelin Glycoprotein P0 Revealed by Mass Spectrometry and Nano Probe Magic Angle Spinning 1H NMR Spectroscopy

Gallego¹,

Blanco²,

Zuylen³

et al. 2001

Journal of Biological Chemistry

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The carbohydrate structures present on the glycoproteins in the central and peripheral nerve systems are essential in many cell adhesion processes. The P0 glycoprotein, expressed by myelinating Schwann cells, plays an important role during the formation and maintenance of myelin, and it is the most abundant constituent of myelin. Using monoclonal antibodies, the homophilic binding of the P0 glycoprotein was shown to be mediated via the human natural keller cell (HNK)-1 epitope (3-O-SO 3 H-GlcUA(␤1-3)Gal(␤1-4)GlcNAc) present on the N-glycans. We recently described the structure of the N-glycan carrying the HNK-1 epitope, present on bovine peripheral myelin P0 (Voshol, H., van Zuylen, C. W. E. M., Orberger, G., Vliegenthart, J. F. G., and Schachner, M. (1996) J. Biol. Chem. 271, 22957-22960). In this study, we report on the structural characterization of the detectable glycoforms, present on the single N-glycosylation site, using state-of-the-art NMR and mass spectrometry techniques. Even though all structures belong to the hybrid-or biantennary complex-type structures, the variety of epitopes is remarkable. In addition to the 3-Osulfate present on the HNK-1-carrying structures, most of the glycans contain a 6-O-sulfated N-acetylglucosamine residue. This indicates the activity of a 6-Osulfo-GlcNAc-transferase, which has not been described before in peripheral nervous tissue. The presence of the disialo-, galactosyl-, and 6-O-sulfosialyl-Lewis X epitopes provides evidence for glycosyltransferase activities not detected until now. The finding of such an epitope diversity triggers questions related to their function and whether events, previously attributed merely to the HNK-1 epitope, could be mediated by the structures described here.The P0 glycoprotein consists of a single immunoglobulin-like domain in its extracellular part, a transmembranous domain, and a cytoplasmic tail. It is the most abundant protein constituent of peripheral myelin. P0 contains a single N-glycosylation site and heterogeneity in its glycosylation pattern that originates from variable contents of fucose, galactose, and sialic acid residues; sulfate; and the HNK-1 carbohydrate epitope (1-4). P0 appears at the initial stage of myelination and contributes to the formation and maintenance of myelin compaction as an adhesion molecule (5). The essential functional role of P0 in the processes of myelination has been demonstrated by creating P0 knockout mice, which show severe hypomyelination and myelin degeneration (5, 6). In humans, several neurological disorders such as Charcot-Marie-Tooth disease, Dejerine-Sottas disease, and congenital hypomyelination have been associated with mutations in the P0 gene (7).It has been reported that the glycan moiety of P0 plays an important role in cell-cell adhesion via homophilic binding. This homophilic binding has been mapped to the SDNGT sequence composing amino acids 91-95, which harbors the single N-glycosylation site on P0 (8). Thus, it was observed that this glycopeptide fragment inhibits cell adhesion t...

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Section: Resultsmentioning

confidence: 99%

Section: Characterization Of N-glycans Of Bovine Peripheral Myelin P0mentioning

confidence: 99%

Epitope Diversity of N-Glycans from Bovine Peripheral Myelin Glycoprotein P0 Revealed by Mass Spectrometry and Nano Probe Magic Angle Spinning 1H NMR Spectroscopy

Gallego¹,

Blanco²,

Zuylen³

et al. 2001

Journal of Biological Chemistry

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“…2) and HMBC spectra (see supplementary data, Fig. S1)) obtained on the de-O-acetylated PS sample, combined with literature data (Bock et al 1984;Strecker et al 1989;Breg et al 1988;Grönberg et al 1989Grönberg et al , 1992Dasgupta et al 1994) of carbohydrate chains containing similarly linked monosaccharide residues, helped to identify the sugar constituents and assign proton and carbon resonances (Table 1). Thus, residue A was determined to be the →2,3)-D-Galp-(1→ unit, residue A′ was assigned to the →3)-D-Galp-(1→ unit, while both residues B and B′ belonged to the →4)-D-GlcpNAc-(1→.…”

Section: Resultsmentioning

confidence: 99%

Discovery and characterization of a fructosylated capsule polysaccharide and sialylated lipopolysaccharide in a virulent strain ofActinobacillus suis

Deutschmann

Boncheff

MacInnes

et al. 2011

Biochem. Cell Biol.

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We are developing a serotyping system for Actinobacillus suis based on its capsule (K) and lipopolysaccharide O-chain (O) structures. Previously, we have shown that less virulent strains of this swine pathogen express a (1→6)-β-D-glucan as both K- and O-chain polysaccharides and were serologically classified as K:1/O:1. Here, we show that representative A. suis strains with a high (H91-0380; serotype K:2/O:2) and intermediate (C84; serotype K:2/O:1) degree of virulence possess a capsule polysaccharide (K:2) composed of an O-acetylated diglycosyl phosphate repeat decorated with fructose: [→4)-3-O-Ac-β-D-GlcpNAc-(1→3)-[β-D-Fruf-(2→2)]-α-D-Galp-(1→PO(4)(-)→]. In addition, the serotype O:2 lipopolysaccharide was shown to express a sialylated O-chain [→3)-β-D-Galp-(1→4)-[Neu5Ac-(2→3)-α-D-Galp-(1→6)]-β-D-Glcp-(1→6)-β-D-GlcpNAc-(1→]. As (1→6)-β-D-glucan is ubiquitous in the environment, low levels of antibodies in the animals are predicted to prevent disease by K:1/O:1 strains. The greater potential associated with K:2/O:2 and K:2/O:1 strains is most likely due to the absence of (1→6)-β-D-glucan as the K antigen and, in the case of K:2/O:2, the presence of sialic acid in the lipopolysaccharide, a nonulosonic acid known to promote evasion of host recognition.

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“…The signal marked by an asterisk is attributed to an impurity in the sample . of the lactose portion at the reducing terminus of ceramide glycanase-released glycolipid oligosaccharides are well documented (compare Dasgupta et al ., 1994) .…”

Section: Resultsmentioning

confidence: 99%

Chemical and Immunological Characterization of Galactosyl‐β1‐3‐Globoside in Bovine, Human, and Rat Brain

Dasgupta

Hogan

Halbeek

1995

Journal of Neurochemistry

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Our studies of bovine brain neutral glycosphingolipids (Ngsls) have revealed the presence of several short‐chain (containing ‐CHO 1–4) and previously uncharacterized long‐chain (−CHO > 4–5) Ngsls. We reported the structural characterization of brain GgOse4Cer (GA1) and have now purified another brain Ngsl to homogeneity. The purified Ngsl migrated close to standard GgOse4Cer and nLcOse5Cer on a TLC plate employing two different solvent systems. The carbohydrate molar composition indicated the presence of Gal/Glc/GalNAc in a ratio of 2.8:1.0:0.9. Five permethylated alditol acetate peaks were characterized as 2,3,4,6‐OMe4Gal, 2,4,6‐OMe3Gal, 2,3,6‐OMe3Gal, 2,3,6‐OMe3Glc, and 4,6‐OMe2GalNAcMe by gas chromatography‐mass spectrometry. The anomeric carbohydrate sequence has been determined by specific exoglycosidase digestion. Six‐hundred megahertz 1H NMR spectroscopy of the oligosaccharide released by ceramide glycanase hydrolysis confirmed the structure of the Ngsl as Galβ1‐3GalNAcβ1‐3Galα1‐4Galβ1‐4Glc\1‐1Cer or IV3GalGbOse4Cer. Using the immunooverlay technique with anti‐stage‐specific embryonic antigen 3 antibody, it was found in bovine, rat, and normal adult human brain and bovine myelin, but not in human or rat myelin.

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Branched Monosialo Gangliosides of the Lacto-Series Isolated from Bovine Erythrocytes: Characterization of a Novel Ganglioside, NeuGc-Isooctaosylceramide

Cited by 16 publications

References 0 publications

Epitope Diversity of N-Glycans from Bovine Peripheral Myelin Glycoprotein P0 Revealed by Mass Spectrometry and Nano Probe Magic Angle Spinning 1H NMR Spectroscopy

Epitope Diversity of N-Glycans from Bovine Peripheral Myelin Glycoprotein P0 Revealed by Mass Spectrometry and Nano Probe Magic Angle Spinning 1H NMR Spectroscopy

Discovery and characterization of a fructosylated capsule polysaccharide and sialylated lipopolysaccharide in a virulent strain ofActinobacillus suis

Chemical and Immunological Characterization of Galactosyl‐β1‐3‐Globoside in Bovine, Human, and Rat Brain

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