Direct structural analysis of 2-aminoacridone derivatized oligosaccharides by high-performance liquid chromatography/mass spectrometric detection

Camilleri, Patrick; Tolson, David; Birrell, Helen

doi:10.1002/(sici)1097-0231(19980214)12:3<144::aid-rcm133>3.0.co;2-7

Cited by 30 publications

(18 citation statements)

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“…In this respect, a large number of derivatization procedures for mono-and oligosaccharides have been described in the literature, most of which have been detailed in a recent review [4]. For example, 2-aminoacridine (2-AMAC) as a sensitive fluorophore, has been used for the detection of monosaccharides, and of neutral and charged oligosaccharides by electrospray ionization (ESI) and matrix-assisted laser desorption/ionization (MALDI) MS [5,6]. Another reagent, 3-acetamido-6-aminoacridine (AAAc), has been used for analysis of N-linked glycans at the picomole level and yielded in higher sensitivities then AMAC [7].…”

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confidence: 99%

Influence of the labeling group on ionization and fragmentation of carbohydrates in mass spectrometry

Lattová

Snovida

Perreault

et al. 2005

J. Am. Soc. Mass Spectrom.

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The ionization and fragmentation behaviors of carbohydrate derivatives prepared by reaction with 2-aminobenzamide (AB), 1-phenyl-3-methyl-5-pyrazolone (PMP), and phenylhydrazine (PHN) were compared under identical mass spectrometric conditions. It has been shown that the intensities of signals in MS spectra depend on the kind of saccharides investigated and reducing end labels used. PMP sialyllactose, when ionized by ESI/MALDI, produced a mixture of ϩ ions. PMP-and reduced AB-sialyllactose produced only Y-type fragment ions under both MS/MS sources. In the electrospray ionization (ESI)-MS/MS spectrum of PHN-sialyllactose, abundant ions corresponded to B, Z cleavages and in its MALDI-MS/MS spectrum, the abundant ions were consistent with Y glycosidic cleavages with the concurrence of B, C, and cross-ring fragment ions. In the MALDI-MS spectra of oligosaccharides acquired immediately after derivatization, it was possible to detect only PHN derivatives. After purification, spectra of all three types of derivatives showed high signal-to-noise ratios with the most abundant ions observed for AB reduced saccharides. [M ϩ Na] ϩ ions were the dominant products and their fragmentation patterns were influenced by the type of the labeling and the kind of oligosaccharide considered. In the MALDI-PSD and -MS/MS spectra of AB-derivatized glycans, higher m/z fragment ions corresponded to B and Y cleavages and the loss of bisecting GlcNAc appeared as a weak signal or was not detected at all. Fragmentation patterns observed in the spectra of hybrid/complex PHN and PMP glycans were more comparable-higher m/z fragments corresponded to B and C glycosidic cleavages. For PHN glycans, the abundance of ions resulting from the loss of bisecting GlcNAc depended on the number of residues linked to the 6-positioned mannose. Also, PHN and PMP derivatives produced cross-ring cleavages with abundances higher than observed in the spectra of AB derivatized oligosaccharides. For high-mannose glycans, the most informative cleavages were provided by AB and PHN type of labeling. Glycosylation is also highly sensitive to alterations of cellular function, and altered protein glycosylation is diagnostic of a number of disease states including, for example, rheumatoid arthritis and cancer [3]. Therefore, the growing interest in understanding the biological functions of carbohydrates has stimulated the development of methods for their improved analysis.In order to detect saccharides by UV/fluorescence and also to ease their characterization by mass spectrometry (MS), introducing a chromophore into the molecules has received increasing attention. In this respect, a large number of derivatization procedures for mono-and oligosaccharides have been described in the literature, most of which have been detailed in a recent review [4]. For example, 2-aminoacridine (2-AMAC) as a sensitive fluorophore, has been used for the detection of monosaccharides, and of neutral and charged oligosaccharides by electrospray ionization (ESI) and matrix-

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confidence: 99%

Influence of the labeling group on ionization and fragmentation of carbohydrates in mass spectrometry

Lattová

Snovida

Perreault

et al. 2005

J. Am. Soc. Mass Spectrom.

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“…The use of ESI to study carbohydrates is well documented,7–16 and has been employed in conjunction with a range of mass analysers including time‐of‐flight (TOF),7,, 8,, 15,, 16 magnetic sector,11 Fourier transform ion cyclotron resonance (FT‐ICR),12 and ion trap (QIT) mass spectrometers,13,, 14 for the analysis of oligosaccharides,13,, 14 glycopeptides17 and glycolipids 12,. 18 A limitation of this technique, however, is that the hydrophilic character of oligosaccharides reduces the overall sensitivity of ESI‐MS; consequently, oligosaccharide samples require derivatizion19 or nanoelectrospray20 to improve the ionisation efficiency.…”

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confidence: 99%

Structural analysis of oligosaccharides by atmospheric pressure matrix‐assisted laser desorption/ionisation quadrupole ion trap mass spectrometry

Creaser

Reynolds

Harvey

2001

Rapid Comm Mass Spectrometry

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An ion source incorporating a fibre optic interface has been constructed for atmospheric pressure matrix-assisted laser desorption/ionisation quadrupole ion trap mass spectrometry. The configuration has been applied to the study of linear and complex oligosaccharides. Multi-stage tandem mass spectrometry (MSn, n = 2-4) experiments carried out in the ion trap enable extended fragmentation pathways to be investigated that yield structural information. Collisional activation of sodiated oligosaccharides, as demonstrated on the model compound maltoheptaose, produces primarily B and Y fragments resulting from cleavage of glycosidic bonds; fragments from cross-ring cleavages are also observed following further stages of tandem mass spectrometry, providing additional linkage information. The analyses of mixtures of complex oligosaccharides are demonstrated for N-linked glycans from chicken egg glycoproteins and a ribonuclease glycan mixture. Mass spectrometric and tandem mass spectrometric data for sugars with molecular weights up to 4000 Da is shown for mixtures of linear dextrans and N-linked glycans. The use of MSn (n = 3, 4) on these complex molecules enabled structural information to be elucidated that confirms data observed in the MS/MS spectra.

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“…The approach coupled a base-catalyzed β-elimination with a Borch reaction (reductive amidation) with 2-AMAC. This approach for carbohydrate analysis has been used extensively for the quantitation and compositional analysis via fluorescenceassisted carbohydrate electrophoresis [38,40,41] and adapted to HPLC and LCMS [42,43]. This report is the first, however, to use a synthetic standard to provide absolute quantitation for the AMAC-xylose on a biologically relevant scale.…”

Section: Discussionmentioning

confidence: 99%

Incomplete Elongation of the Chondroitin Sulfate Linkage Region on Aggrecan and Response to Interleukin-1β

Frankenberger

Borgia

Edirisinghe

et al. 2013

Connective Tissue Research

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Aggrecan is the prominent proteoglycan in cartilage and is modified with approximately 100 chondroitin sulfate (CS) chains through a tetrasaccharide linkage structure. In osteoarthritis (OA), the viscoelastic properties of cartilage are compromised on both the quantity and integrity of aggrecan core protein expressed as well as reduced overall CS chain length. Herein, we postulated that chronic low-level inflammation may also contribute to OA progression by promoting regulatory mechanisms in early CS biosynthesis that yield incomplete linkage structures on aggrecan. To test this idea, chondrocytes extracted from human tali were cultured in alginate beads and challenged with 5 ng/mL IL-1β as a model for chronic inflammation leading to OA progression. Novel mass spectrometry-based methods were devised to detect and quantify partially elongated linkage structures relative to control cultures. The total mole fraction of unelongated xylose residues per aggrecan was significantly less (p = 0.03) after IL-1β treatment compared to control cultures, with unelongated xylose residues constituting between 6% and 12% of the fraction of total CS measured. A portion (<1%) of the partially elongated linkage structures was found to be either phosphorylated or sulfated. These results establish quantitative mass spectrometry as a very sensitive and effective platform for evaluating truncated proteoglycan linkage structures. Our observations using this method suggest a possible role for aberrant linkage structure elongation in OA progression.

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Direct structural analysis of 2-aminoacridone derivatized oligosaccharides by high-performance liquid chromatography/mass spectrometric detection

Cited by 30 publications

References 9 publications

Influence of the labeling group on ionization and fragmentation of carbohydrates in mass spectrometry

Influence of the labeling group on ionization and fragmentation of carbohydrates in mass spectrometry

Structural analysis of oligosaccharides by atmospheric pressure matrix‐assisted laser desorption/ionisation quadrupole ion trap mass spectrometry

Incomplete Elongation of the Chondroitin Sulfate Linkage Region on Aggrecan and Response to Interleukin-1β

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