Konformationsanalyse, XXIV. Bestimmung der Konformationen von Tri‐ und Tetrasaccharid‐Sequenzen der Core‐Struktur von N‐Glycoproteinen. Problem der (1 → 6)‐glycosidischen Bindung

Paulsen, Hans; Peters, Thomas; Sinnwell, Volker; Lebuhn, Rolf; Meyer, Bernd

doi:10.1002/jlac.198419840514

Cited by 58 publications

(21 citation statements)

References 34 publications

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“…In modelling the 3D structure of the whole oligosaccharide part of globotriaosylceramide using the GESA programme [32], a good agreement with the results just discussed was obtained. This was rather surprising in view of the roughness of the HSEA model [31] underlying GESA.…”

Section: Calculated With Eqn Rij = R K L ( O K L / O T J ) 1 'supporting

confidence: 73%

“…The study of native, undeuterated, glycosphingolipids puts to use important long-range interactions involving hydroxyl protons, which provide a broader basis for a reliable determination of the solution conformation of the oligosaccharide segments. The 4, y representation of the trisaccharides studied was obtained exclusively from NOE-derived distance constraints and was compared with that obtained by molecular mechanics [30] and HSEA [31] computations (using programme GESA [32]). In the case of the Gal(a1-4)GalP linkage of 1 both computational methods predicted two energy minima which are in very good agreement with NOE-derived conformations.…”

Section: Discussionmentioning

confidence: 99%

“…The energy-minimum calculations were done using the GESA programme [32] and molecular mechanics programme MM2(85) [30] running on the same computer. In the case of MM2 calculations for the Gal(al-4)Galp disaccharide segment a full grid search in 4, y space was done in 10' steps.…”

Section: Conjormutional Calculationsmentioning

confidence: 99%

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Three‐dimensional structure of the oligosaccharide terminus of globotriaosylceramide and isoglobotriaosylceramide in solution

Poppe

Dąbrowski

Lieth

et al. 1990

European Journal of Biochemistry

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Spatial structures of the oligosaccharide parts of globotriaosylceramide, Gal(al-4)Gal(fll-4)Glc(fl1-1)Cer (Cer = ceramide) and isoglobotriaosylceramide, Gal(al-3)Gal(/3l-4)Glc(/l1-1)Cer were investigated in (C2H3)2S0 solution by means of laboratory and rotating frame NOE, hydroxyl protons being used as long-range sensors defining the distance constraints. Both oligosaccharides were found to exist in more than one conformation interconverting rapidly on the NMR time scale. The conformation of the Gal(al-4)Gal(~1-4)Glc/3 trisaccharide dissolved in 2 H 2 0 appeared to be the same as that of the corresponding part of the glycosphingolipid in (C2H3)2S0 solution.Globotriaosylceramide Gal(~1-4)Glc(/31 -l)Cer; I] and isoglobotriaosylceramide Gal(/ll-4)Glc(fl1-1)Cer; 21 belong to the globo series of glycosphingolipids found in many different mammalian tissues [I]. The former was recognized as an antigen of the P blood group system, whilst 2 was found to be associated with malignant neoplasms [I, 21. Recent findings have shown that the Gal(a1-4)GalB segment of many glycosphingolipids can act as an attachment site for bacteria, bacterial toxins and viruses [3,4]. The importance of the three-dimensional (3D) structure of this epitope in relation to its biological role has been highlighted [3,4] and a detailed conformational investigation of the corresponding disaccharide, galabiose, has been published [5].The spatial structure of oligosaccharides can be determined, in principle, from experimental data (NOE, coupling constants, chemical shifts) and/or from theoretical calculations. Since the latter are still far from being able to deliver unequivocal solutions, experimental approaches remain the main source of structural information. It must be realized, however, that an experimentally derived conformation does not necessarily correspond to a single state, but may result rather as an average of many, or even an infinite number, of states [6, 71. Apart from possible, but not very likely, radical progress in computational methods, reliable verification of one-state vs multiple-state conformational models requires a Correspondence to J. Dabrowski, Max-Planck-Institut fur Medizinische Forschung, Jahnstrasse 29, D-6900 Heidelberg, Federal Republic of Germany Abbreviations. Cer, ceramide; COSY, correlation spectroscopy; ID, 2D and 3D. one-, two-and three-dimensional; DANTE, delays alternating with nutations for tailored excitation; FID, free induction decay; GESA, geometry of saccharides programme; HOHAHA spectroscopy, homonuclear Hartmann-Hahn spectroscopy; HSEA, hardsphere exo-anomeric method; ROE, rotating frame nuclear Overhauser effect; ROESY, 2D ROE spectroscopy; TOCSY, total correlation spectroscopy ; TPPI, time-proportional phase incrementation. greater number of experimentally based constraints, in fact more than can presently be obtained with the aid of NMR spectroscopy. In particular, NOE contacts, which are found to be abundant and highly effective as constraints in the conformational analysis of proteins, oligopeptid...

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Section: Calculated With Eqn Rij = R K L ( O K L / O T J ) 1 'supporting

confidence: 73%

Section: Discussionmentioning

confidence: 99%

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Three‐dimensional structure of the oligosaccharide terminus of globotriaosylceramide and isoglobotriaosylceramide in solution

Poppe

Dąbrowski

Lieth

et al. 1990

European Journal of Biochemistry

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“…No direct evidence allowed discrimination of the 'H and 13C resonances related to GalB1-6 and Galfil-4, except for the couples H-5/C-5 and H-6/C-6 which were finally identified by the two COSY spectra. Nevertheless, the Gal-G6 resonances observed at 72.07 ppm and 73.71 ppm appear to be shifted slowly upfield compared with the corresponding values of Gal-6' in the reference compound Galfil4GlcNAc~l-2Manctl-6Manfi1-4GlcNAc [15]. Moreover the Gal-G6H-4 resonance measured at 6 = 3.968 ppm shows a downfield shift effect ( + 0.030 ppm) in comparison with the H-4 signal of Gal-6' for the reference compound [14].…”

Section: Structural Determinationmentioning

confidence: 87%

Characterization of a novel type of chain‐terminator Galβ1–6Galβ1–4)GlcNAc in an oligosaccharide related to N‐glycosylated protein glycans isolated from GM₁ the urine of patients with gangliosidosis

Michalski

Lemoine

Wieruszeski

et al. 1991

European Journal of Biochemistry

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Two new oligosaccharides were isolated from the urine of a patient with G M gangliosidosis. Final purification of the oligosaccharides was accomplished by capillary supercritical fluid chromatography. Structural analysis was by chemical analysis, chemical-ionization mass spectrometry and 400-MHz H-NMR spectroscopy, leading to two primary structures. The first is derived from a classical triantennary N-acetyllactosamine-type glycan :Gal/31-4GlcNAc~1-4(Gal~1-4GlcNAc~1-2)Mancrl-3Man~1-4GlcNAc.The second is unusual with a terminal disaccharide GalPl-6Ga1, which had not yet been described for glycans of the N-acetyllactosamine type:Gal~~1-6Gal~1-4GlcNAc~1-2Man~l-6Man~1-4GlcNAc.Urine of patients suffering from glycoproteinosis contains a large amount of oligosaccharides or glycopeptides which originate from incomplete lysosomal catabolism of glycoprotein glycans [I -31. Isolation and structural analysis of compounds accumulated in this kind of diseases are of interest and importance since they provide valuable information on the broad spectrum of glycan structures which normally exist in human cellular glycoproteins [4,5]. In this context, studying minor oligosaccharides present in glycoproteinosis urine may provide structural information on some unusual carbohydrate determinants naturally occurring in glycoconjugate glycans. As a result of the P-galactosidase deficiency occuring in GM1 gangliosidosis [6], a number of different galactosyl oligosaccharides are excreted in the urine of patients [7-91. We report here detailed structural analysis of two minor urinary oligosaccharides, one of which presents a new type of galactosyl linkage never described before for the N-acetyllactosamine-type glycans. MATERIALS AND METHODS UrineUrine (8 1) was collected from a patient with G M I gangliosidosis type 1. The urine was chilled at -20 'T immediately after collection and was stored without preservatives. Ahhreviutions. SFC-CI, supercritical-fluid-chromatography chemical ionization; FAB-MS, fast-atom-bombardment mass spectrometry; Hex, hexose; HexNAc, 2-deoxy-N-acetylamino-~-hexose cosy; correlated spectroscopy. Isolation of neutral oligosaccharidesNeutral oligosaccharides were obtained as previously described [lo] and directly applied to an activated charcoalCelite (Sigma) column (10 cm x 100 cm). The column was washed with distilled water and adsorbed material stepwise eluted with 10 1 ethanol of increased concentration (1 .5 -50%).Further separation and purification of the oligosaccharides were carried out by descending paper chromatography (Whatman no 3 paper) using a solvent system of ethyl acetate/pyridine/acetic acid/water (5 : 5 : 1 : 3, by vol.), performed over 4 -12 days. Analytical proceduresThe molar ratios of hexoses and N-acetylhexosamines were determined by GLC analysis of the trifluoroacetyl derivatives obtained after methanolysis of oligosaccharides (methanol/ 0.5 M HC1; 24 h, 80°C). Methylation analysis was performed according to [Ill. Supercritical-fluid-chromatography mass spectrometryThe oligosaccharides w...

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“…The results emphasize that the globo-GSLs show different receptor properties in membranes as compared to artificial surfaces ( Fig. 1 (15). Ten panels, each with 11 lanes, are shown after spray detection with anisaldehyde (to the left), and after autoradiography from overlay with radiolabeled bacteria (Upper) and monoclonal antibodies (Lower) with specificity for GbO3 (PK002), GbO4 (MC-631), GbO5 (MAS 033b), and GgO3 (2D4).…”

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confidence: 86%

Saccharide orientation at the cell surface affects glycolipid receptor function.

Strömberg

Nyholm

Pascher

et al. 1991

Proc. Natl. Acad. Sci. U.S.A.

173

114

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Three allelic variants of P-pilus-associated G-adheslns (ectins) with different cell-binding properties were recently described. Here we have analyzed Eschenchia cofl HB101 strains expressing the recombinant G-adhesin variants for their ability to agglutinate erythrocytes from various species as this relates to the glycosphingolipid (GSL) MATERIALS AND METHODSBacteria, Growth Conditions, and Labeling. E. coli strain HB101 was used to express the P pilus-associated G-adhesins PapGJ96, PrsGJ96, and PapGAD1LO carried by the recombinant plasmids pPAP5, pPAP601, and pPIL110-35, respectively (10). Plasmid pPAP5 consists of the vector pBR322 and a 9.7-kilobase (kb) EcoRI/BamHI chromosomal fragment derived from E. coli J96 and encodes F13 P pili with the PapGJ96 adhesin (10). Plasmid pPAP601 is a pACYC184 derivative carrying another E. coli J96 chromosomal fragment encoding serologically identical F13 pili but having the PrsGJ% adhesin (10). Plasmid pPIL110-35 is a pACYC184 derivative containing a 16-kb EcoRI fragment of E. coli AD110 and encoding F72 P pili with the PapGAD110 adhesin (10).For the glycolipid binding assay, the bacteria were cultivated overnight at 37TC on Luria agar plates (10) supplemented with carbenicillin, chloramphenicol, and tetracycline (100, 20, and 10 jig/ml, respectively). Metabolically labeled bacteria were obtained by addition of [35S]methionine (600 Ci/mmol; 150-200 ,uCi per plate; 1 Ci = 37 GBq; Amersham). After growth, the bacteria were harvested by centrifugation, washed twice in phosphate-buffered saline (PBS) (pH 7.3), and resuspended in PBS.Hemagglutination Assay. For hemagglutination, 10 of fresh bacteria (109 cells per ml) and 10 of erythrocyte suspension (4%), both suspended in PBS at pH 7.3, were mixed on a glass slide. During gentle mixing for 5 min at room temperature, agglutination was visualized and scored (see Table 1).Erythrocyte Glycolipids. For the preparation of total acidic and neutral GSLs (10), fresh erythrocytes were washed twice in saline and 100 ml of erythrocyte concentrate was shaken continuously together with toluene and water (65 ml and 30 ml, respectively). After centrifugation (10,000 x g for 5 min), the purified membranes (10 g) at the toluene/water interface were extracted twice with methanol (100 ml), once with chloroform/methanol (2:1) (100 ml), and once with methanol (100 ml) for 25 min at 70TC. 9340The publication costs of this article were defrayed in part by page charge payment. This article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. §1734 solely to indicate this fact.

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Konformationsanalyse, XXIV. Bestimmung der Konformationen von Tri‐ und Tetrasaccharid‐Sequenzen der Core‐Struktur von N‐Glycoproteinen. Problem der (1 → 6)‐glycosidischen Bindung

Cited by 58 publications

References 34 publications

Three‐dimensional structure of the oligosaccharide terminus of globotriaosylceramide and isoglobotriaosylceramide in solution

Three‐dimensional structure of the oligosaccharide terminus of globotriaosylceramide and isoglobotriaosylceramide in solution

Characterization of a novel type of chain‐terminator Galβ1–6Galβ1–4)GlcNAc in an oligosaccharide related to N‐glycosylated protein glycans isolated from GM₁ the urine of patients with gangliosidosis

Saccharide orientation at the cell surface affects glycolipid receptor function.

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Konformationsanalyse, XXIV. Bestimmung der Konformationen von Tri‐ und Tetrasaccharid‐Sequenzen der Core‐Struktur von N‐Glycoproteinen. Problem der (1 → 6)‐glycosidischen Bindung

Cited by 58 publications

References 34 publications

Three‐dimensional structure of the oligosaccharide terminus of globotriaosylceramide and isoglobotriaosylceramide in solution

Three‐dimensional structure of the oligosaccharide terminus of globotriaosylceramide and isoglobotriaosylceramide in solution

Characterization of a novel type of chain‐terminator Galβ1–6Galβ1–4)GlcNAc in an oligosaccharide related to N‐glycosylated protein glycans isolated from GM1 the urine of patients with gangliosidosis

Saccharide orientation at the cell surface affects glycolipid receptor function.

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Characterization of a novel type of chain‐terminator Galβ1–6Galβ1–4)GlcNAc in an oligosaccharide related to N‐glycosylated protein glycans isolated from GM₁ the urine of patients with gangliosidosis