High-Resolution Capillary Gel Electrophoresis of Reducing Oligosaccharides Labeled with 1-Aminopyrene-3,6,8-trisulfonate

Guttman, András; Chen, Fu Tai A.; Evangelista, Ramon A.; Cooke, Nelson

doi:10.1006/abio.1996.0034

Cited by 179 publications

(133 citation statements)

References 16 publications

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“…24) in the presence of mannoheptose (100 pmol) as internal standard (26). After drying under vacuum, the reaction products were mixed with 0.4 l of 0.2 M 1-aminopyrene-3,6,8-trisulfonate (APTS; Interchim, Montluçon, France) in 15% acetic acid and 0.4 l of a 1 M sodium cyanoborohydrure solution dissolved in tetrahydrofuran (27). The reaction was performed for 90 min at 55°C and was quenched by addition of 20 l of water.…”

Section: Ce and Mannooligosaccharide Cap Quantificationmentioning

confidence: 99%

Mannosylated Lipoarabinomannans Inhibit IL-12 Production by Human Dendritic Cells: Evidence for a Negative Signal Delivered Through the Mannose Receptor

Nigou

Zelle‐Rieser

Gilleron

et al. 2001

The Journal of Immunology

370

336

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IL-12 is a key cytokine in directing the development of type 1 Th cells, which are critical to eradicate intracellular pathogens such as Mycobacterium tuberculosis. Here, we report that mannose-capped lipoarabinomannans (ManLAMs) from Mycobacterium bovis bacillus Calmette-Guérin and Mycobacterium tuberculosis inhibited, in a dose-dependant manner, the LPS-induced IL-12 production by human dendritic cells. The inhibitory activity was abolished by the loss of the mannose caps or the GPI acyl residues. Mannan, which is a ligand for the mannose receptor (MR) as well as an mAb specific for the MR, also inhibited the LPS-induced IL-12 production by dendritic cells. Our results indicate that ManLAMs may act as virulence factors that contribute to the persistence of M. bovis bacillus Calmette-Guérin and M. tuberculosis within phagocytic cells by suppressing IL-12 responses. Our data also suggest that engagement of the MR by ManLAMs delivers a negative signal that interferes with the LPS-induced positive signals delivered by the Toll-like receptors.

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Section: Ce and Mannooligosaccharide Cap Quantificationmentioning

confidence: 99%

Mannosylated Lipoarabinomannans Inhibit IL-12 Production by Human Dendritic Cells: Evidence for a Negative Signal Delivered Through the Mannose Receptor

Nigou

Zelle‐Rieser

Gilleron

et al. 2001

The Journal of Immunology

370

336

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“…Equilibrium Dialysis Studies-3Ј-SO 4 -Lewis X and a glucose pentasaccharide (Glc5) prepared from dextran by mild acid hydrolysis (10) were derivatized with 9-aminopyrene-1,4,6-trisulfonic acid (APTS) by reductive amination as described (11). Binding was performed in a two-chamber Teflon Micro-Equilibrium dialyzer (Amika, Inc.) utilizing ultrathin 10,000-dalton cut-off membranes (The Nest Group, Inc.).…”

Section: Materials-man/galnac-4-somentioning

confidence: 99%

The Mannose/N-Acetylgalactosamine-4-SO4Receptor Displays Greater Specificity for Multivalent than Monovalent Ligands

Roseman

Baenziger²

2001

Journal of Biological Chemistry

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Recognition of carbohydrates on glycosylated molecules typically requires multivalent interactions with receptors. Monovalent forms of terminal saccharides engaged by the receptor binding sites typically display weak affinities in the mM range and poor specificity. In contrast, multivalent forms of the same saccharides are bound with strong affinity (10 ؊7 -10 ؊9 M) and significantly greater specificity. Although multivalency can readily account for increased affinity, the molecular basis for enhanced specificity is not well understood. We have examined the specificity of the cysteine-rich domain of the mannose/GalNAc-4-SO 4 receptor using monovalent and multivalent forms of the trisaccharide GalNAc␤1,4GlcNAc␤1,2Man␣ (GGnM) sulfated at either the C4 (S4GGnM) or C3 ( We previously demonstrated that glycoproteins such as LH 1 and thyrotropin bearing N-linked oligosaccharides terminating with ␤1,4-linked GalNAc-4-SO 4 are recognized by a receptor located in hepatic endothelial cells, the Man/GalNAc-4-SO 4 receptor, and are rapidly removed from the circulation (1-4). Rapid clearance in conjunction with stimulated release from dense core storage granules in LH-producing cells located in the anterior lobe of the pituitary produce the episodic rise and fall in serum LH levels that is important for the expression of LH bioactivity in vivo. A novel feature of the Man/GalNAc-4-SO 4 receptor is its capacity to bind carbohydrate moieties terminating with Man and GalNAc-4-SO 4 at physically distinct domains that are not structurally related. The binding site for GalNAc-4-SO 4 is located in the cysteine-rich domain found at the N terminus of the Man/GalNAc-4-SO 4 receptor (5). The Cys-rich domain is a member of the ␤-trefoil family of proteins that includes proteins such as acidic fibroblast growth factor. The binding site is a neutral pocket that accommodates the sulfate group, which accounts for the major interactions with the protein (6). Inhibition and modeling studies with monovalent ligands have indicated that the binding site in the Cys-rich domain can also accommodate saccharides with terminal Gal or GalNAc when the sulfate is located at C3 rather than C4 (6, 7).The latter observations were unexpected because we had reported that bovine serum albumin substituted with 6 -8 molecules of SO 4 -4-GalNAc␤1,4GlcNAc␤1,2Man␣ (S4GGnM-BSA) is removed from the circulation at a rate that is at least 12-fold greater than that seen for bovine serum albumin substituted with 6 -8 molecules of SO 4 -3-GalNAc␤1,4GlcNAc␤1,2Man␣ (S3GGnM-BSA). Furthermore, isolated hepatic endothelial cells do not bind and internalize S3GGnM-BSA, and the purified Man/GalNAc-4-SO 4 receptor does not display significant binding of S3GGnM-BSA in precipitation assays (2, 3). We have recently determined that the Man/GalNAc-4-SO 4 receptor must be dimeric and engage at least two terminal GalNAc-4-SO 4 moieties on separate oligosaccharides to mediate uptake by hepatic endothelial cells with a K d of 1.63 ϫ 10 Ϫ7 M (8). These observations raise the possibility th...

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“…Glycosylation is one of the major and most complicated forms of post-translational modifications that plays essential roles in the activity and effector function of monoclonal antibodies [3] demanding improved glycoanalytical methods. Frequently 3/13 used techniques for carbohydrate analysis are mass spectrometry (MS) [4], liquid chromatography (LC) [5,6], capillary electrophoresis (CE) [7][8][9], some combination of them [10][11][12] and if necessary, nuclear magnetic resonance spectroscopy (NMR) [13,14].…”

Section: Introductionmentioning

confidence: 99%

“…Studies have shown that stronger acids were able to increase derivatization yield [29], but their use was associated with higher sialic acid loss [30]. Among the numerous sugar labeling dyes the 8-aminopyrene-1,3,6-trisulfonic acid (APTS) [7] and 8-aminonaphthalene-1,3,6-trisulfonic (ANTS) [31] are the mostly used fluorophores in sugar analysis using electric field mediated separation methods as they are multiply charged and provide high fluorescent yield [32].…”

Section: Introductionmentioning

confidence: 99%

Evaporative fluorophore labeling of carbohydrates via reductive amination

Reider

Szigeti

Guttman

2018

Talanta

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As analytical glycomics became to prominence, newer and more efficient sample preparation methods are being developed. Albeit, numerous reductive amination based carbohydrate labeling protocols have been reported in the literature, the preferred way to conduct the reaction is in closed vials. Here we report on a novel evaporative labeling protocol with the great advantage of continuously concentrating the reagents during the tagging reaction, therefore accommodating to reach the optimal reagent concentrations for a wide range of glycan structures in a complex mixture. The optimized conditions of the evaporative labeling process minimized sialylation loss, otherwise representing a major issue in reductive amination based carbohydrate tagging. In addition, complete and uniform dispersion of dry samples was obtained by supplementing the low volume labeling mixtures (several microliters) with the addition of extra solvent (e.g., THF).Evaporative labeling is an automation-friendly glycan labeling method, suitable for standard open 96 well plate format operation. Graphical abstract 2/13

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High-Resolution Capillary Gel Electrophoresis of Reducing Oligosaccharides Labeled with 1-Aminopyrene-3,6,8-trisulfonate

Cited by 179 publications

References 16 publications

Mannosylated Lipoarabinomannans Inhibit IL-12 Production by Human Dendritic Cells: Evidence for a Negative Signal Delivered Through the Mannose Receptor

Mannosylated Lipoarabinomannans Inhibit IL-12 Production by Human Dendritic Cells: Evidence for a Negative Signal Delivered Through the Mannose Receptor

The Mannose/N-Acetylgalactosamine-4-SO4Receptor Displays Greater Specificity for Multivalent than Monovalent Ligands

Evaporative fluorophore labeling of carbohydrates via reductive amination

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