High-Resolution 1H-Nuclear Magnetic Resonance Spectroscopy of Oligosaccharide-Alditols Released from Mucin-Type O-Glycoproteins

Kamerling, Johannis P.; Vliegenthart, Johannes F.G.

doi:10.1007/978-1-4757-9474-8_1

Cited by 75 publications

(61 citation statements)

References 112 publications

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“…As observed in Table 1, these data give more reliable information about the nature of the core structure and permit to unambiguously discriminate between cores 1, 2 and 3, as well as their eventual sialylated counterparts present in the analysed components. These attributions were in good agreement with structural reporter groups already published for GalNAc-ol substituted in C-3 position by β-Gal or β-GlcNAc and substituted in C-6 by β-GlcNAc or a-NeuAc/Gc residues [8].…”

Section: Isolation Of Oligosaccharide-alditolssupporting

confidence: 83%

“…2 to 9) and NMR parameters of all compounds are shown in Tables 1-8. Systematic analyses revealed that 28 components presented well known structures, which have been already described and will not be further discussed [8]. In contrast, 31 compounds (22, 25, 27 and 31 to 58) exhibited original sequence structures that appear as characteristic of the Triturus alpestris species.…”

Section: Isolation Of Oligosaccharide-alditolsmentioning

confidence: 86%

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Structure elucidation of NeuAc, NeuGc and Kdn-containing O-glycans released from Triturus alpestris oviductal mucins

et al. 2006

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Eggs from Amphibia are surrounded by several layers of jelly that are needed for proper fertilization. Jelly coat is composed of highly glycosylated mucin-type glycoproteins containing up to 60% of carbohydrates, which display a remarkable species-specificity. This material obtained from Triturus alpestris was submitted to reductive beta-elimination and the released oligosaccharide-alditols were further fractionated by HPLC. Structural characterization was performed through a combination of two dimensional (1)H-(1)H and (1)H-(13)C NMR and ESI-MS/MS analysis. Numerous carbohydrate chains are characterized by the presence of the Cad (Sd(a)) determinant, including respectively NeuAc, NeuGc or Kdn as a sialic acid. But the most significant O-glycan sequences which mark the difference between the jelly of T. alpestris and other studies amphibian jellies are polymers of GalNAc(beta 1-4)GlcNAc (LacdiNAc) which form part of the following sequence: HSO(3)(4)(GalNAcbeta 1-4GlcNAcbeta 1-3)(1-3)GalNAcbeta 1-4(GlcNAcbeta 1-3)(0-1)GlcNAcbeta 1-6GalNAc-ol.

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Section: Isolation Of Oligosaccharide-alditolssupporting

confidence: 83%

Section: Isolation Of Oligosaccharide-alditolsmentioning

confidence: 86%

Structure elucidation of NeuAc, NeuGc and Kdn-containing O-glycans released from Triturus alpestris oviductal mucins

et al. 2006

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“…4A). Resulting oligosaccharide fractions were analyzed by MALDI-MS, which demonstrated that all of them still comprised heterogeneous (40,62). c (ϩ) to ϩϩϩϩϩ; 0 -1,600, 1,601-4,000, 4,001-8,000, 8,001-12,000, 12,001-16,000, and 16,001-20,000 area counts, respectively.…”

Section: Isolation Of Klh Oligosaccharides Sharing Carbohydrate Epitomentioning

confidence: 99%

Identification and Characterization of Keyhole Limpet Hemocyanin N-Glycans Mediating Cross-reactivity with Schistosoma mansoni

Geyer

Wuhrer

Resemann

et al. 2005

Journal of Biological Chemistry

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Keyhole limpet hemocyanin (KLH) of the mollusc Megathura crenulata is known to serologically cross-react with Schistosoma mansoni glycoconjugates in a carbohydrate-dependent manner. To elucidate the structural basis for this cross-reactivity, KLH glycans were released from tryptic glycopeptides and fluorescently labeled. Cross-reacting glycans were identified using a polyclonal antiserum reacting with soluble S. mansoni egg antigens, isolated by a threedimensional fractionation scheme and analyzed by different mass spectrometric techniques as well as linkage analysis and exoglycosidase treatment. The results revealed that cross-reacting species comprise ϳ4.5% of released glycans. They all represent novel types of N-glycans with a Fuc(␣1-3)GalNAc(␤1-4)[Fuc(␣1-3)]GlcNAc motif, which is known to occur also in schistosomal glycoconjugates. The tetrasaccharide unit is attached to the 3-linked antenna of a trimannosyl core, which can be further decorated by galactosyl residues, a xylose residue in 2-position of the central mannose and/or a fucose at the innermost N-acetylglucosamine. This study provides for the first time detailed structural data on the KLH carbohydrate entities responsible for cross-reactivity with glycoconjugates from S. mansoni.Hemocyanins act as oxygen-transporting proteins in many arthropod and mollusc species (1). In addition to this biochemical function, the hemocyanin of the Californian giant keyhole limpet Megathura crenulata, a marine gastropod, is known to be a potent immunoactivator (for reviews, see Refs. 2 and 3). Due to these immunostimulatory properties, keyhole limpet hemocyanin (KLH) 2 is widely used in research and clinical studies. Present fields of application are, for example, immunotherapy of bladder cancer (4 -7), based on the assumed expression of Gal(␤1-3)GalNAc determinants as cross-reacting epitopes (8), and its use as a carrier of polysialic acid or low molecular weight haptens, such as synthetic oligosaccharides, gangliosides, or (glyco)peptides, designed for potential application in anticancer therapy (9 -14). Intriguingly, KLH has been further demonstrated to exhibit a carbohydrate-based cross-reactivity with glycoconjugates from Schistosoma mansoni (15) thus allowing the diagnosis of S. mansoni (6, 7, 16), Schistosoma hematobium (17), and Schistosoma japonicum (18) infections by enzymelinked immunosorbent assay (ELISA). Hence, KLH has also been discussed as a potential candidate for vaccination against schistosomiasis (15). On the other hand, agarose beads coated with KLH or KLH-glycopeptides have been shown to mimic in a carbohydrate-dependent manner the hepatic granuloma formation mediated by S. mansoni eggs (19). Therefore, KLH may also be regarded as a model antigen to study the immunopathological mechanisms of schistosome infections.Although it is generally accepted that the oligosaccharide constituents of KLH are of prime significance for its antigenicity and biomedical properties (2), knowledge on the carbohydrate structure of this glycoprotein is still incomp...

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“…While computer calculations such as molecular dynamics simulations describe the conformation on the basis of a set of approximations, experimental information about the actual conformation and dynamic aspects of these molecules is obtained from different types of spectra (Kaptein et al, 1988;Karplus and Pestko, 1990). Structural analysis of oligoand polysaccharides has been carried out successfully with numerous one-, two-and threedimensional NMR methods (Vuister et al, 1989;Hhrd and Vliegenthart, 1993;Kamerling and Vliegenthart, 1993;Siebert et al, 1993;Dabrowski, 1994;Homans, 1995). The most valuable information about conformations obtainable from NMR experiments is based on the measurement of the Nuclear Overhauser Effect (NOE).…”

Section: Free-state Conformationmentioning

confidence: 99%

Carbohydrate–Protein Interaction

Siebert¹,

Lieth²,

Gilleron³

et al. 1996

Glycosciences

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High-Resolution 1H-Nuclear Magnetic Resonance Spectroscopy of Oligosaccharide-Alditols Released from Mucin-Type O-Glycoproteins

Cited by 75 publications

References 112 publications

Structure elucidation of NeuAc, NeuGc and Kdn-containing O-glycans released from Triturus alpestris oviductal mucins

Structure elucidation of NeuAc, NeuGc and Kdn-containing O-glycans released from Triturus alpestris oviductal mucins

Identification and Characterization of Keyhole Limpet Hemocyanin N-Glycans Mediating Cross-reactivity with Schistosoma mansoni

Carbohydrate–Protein Interaction

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