Profiling of 2-aminoacridone derivatised glycans by electrospray ionization mass spectrometry

Charlwood, Joanne; Langridge, J.; Tolson, David; Birrell, Helen; Camilleri, Patrick

doi:10.1002/(sici)1097-0231(19990130)13:2<107::aid-rcm463>3.0.co;2-p

Cited by 40 publications

(14 citation statements)

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“…Among these techniques, derivatization (e.g. permethylation11–13 or reducing‐terminal derivatization14–18) and metal adduction in combination with collision‐induced dissociation (CID)19–26 have proved to be useful in determining the linkage, sequence and branching of oligosaccharides. Interest in ESI tandem mass spectrometry (MS n ) using the negative ion mode for the establishment of sequences and branching patterns is also increasing in the structural analysis of underivatized carbohydrates 7, 27–32.…”

Section: Introductionmentioning

confidence: 99%

Evidence for linkage position determination in known feruloylated mono‐ and disaccharides using electrospray ion trap mass spectrometry

Quéméner

Ralet

2004

J. Mass Spectrom.

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Various feruloylated arabinose- and galactose-containing mono- and disaccharides with known linkage configurations (2-O-(trans-feruloyl)-L-arabinopyranose, 5-O-(trans-feruloyl)-L-arabinofuranose, O-[2-O-(trans-feruloyl)-alpha-L-arabinofuranosyl]-(1-->5)-L-arabinofuranose, and O-[6-O-(trans-feruloyl)-beta-D-galactopyranosyl]-(1-->4)-D-galactopyranose) were analyzed by electrospray ionization mass spectrometry using an ion trap or a quadrupole time-of-flight (Q-TOF) mass analyzer. Collision-induced dissociation (CID) experiments using the two mass analyzers generated similar tandem mass spectrometric (MS/MS) fragmentation patterns. However, the ester-bond cleavage ions were more abundant using the Q-TOF mass analyzer. Compared with the positive ion mode, the negative ion mode produces simpler and more useful CID product-ion patterns. For arabinose-containing feruloylated compounds, results obtained with both analyzers show that it is possible to assign the location of the feruloyl group to the O-2 or O-5 of arabinosyl residues. In the characterization of the 2-O-feruloyl and 5-O-feruloyl linkages, the relative abundance of the cross-ring fragment ions at m/z 265 (-60 u or -62 u after 18O-labelling) and at m/z 217 (-108 u or -110 u after 18O-labelling) play a relevant role. For galactose-containing feruloylated compounds, losses of 60, 90 and 120 Da observed in MS3 experiment correspond to the production of 0,2A1, 0,3A1 and (0,2A1-60 Da) cross-ring cleavage ions, respectively, fixing the location of feruloyl group at the O-6 of the galactose residue.

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Section: Introductionmentioning

confidence: 99%

Evidence for linkage position determination in known feruloylated mono‐ and disaccharides using electrospray ion trap mass spectrometry

Quéméner

Ralet

2004

J. Mass Spectrom.

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“…In structural analysis of carbohydrates, native and derivatized oligosaccharides have been analyzed by MALDI [5][6][7][8][9][10][11][12][13][14]. Metal ion coordinated [15,16] or chemically derivatized [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34] oligosaccharides have been used for ESI analysis. Among those approaches, the method based on MALDI time-of flight/time-offlight (TOF/TOF) tandem mass spectrometry provides good sensitivity and cross-ring cleavage because of the use of high-energy collision-induced dissociation (he-CID) [8 -14].…”

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confidence: 99%

Linkage and branch determination of N-linked oligosaccharides using sequential degradation/closed-ring chromophore labeling/negative ion trap mass spectrometry

Pai

Her

2007

J. Am. Soc. Mass Spectrom.

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A method based on sequential degradation, p-aminobenzoic ethyl ester (ABEE) closed-ring labeling, and negative ion electrospray ionization tandem mass spectrometry is presented for the study of linkage and branch determination for N-linked oligosaccharides. Closed-ring labeling provides greater linkage information than the more popular open-ring reductive amination approach. In addition, after high-performance liquid chromatography (HPLC) separation, closed-ring labeling allows for regeneration of the underivatized oligosaccharide, a requirement for alkaline sequential degradation. The analytical scheme presented here uses HPLC separation of closed-ring labeled oligosaccharides to resolve the mixture into individual forms that undergo subsequent structural analysis by negative ion tandem mass spectrometry. To facilitate complete structural analysis, particularly for larger sugars, the closed-ring labels are removed and the sugars are sequentially degraded by controlled alkaline hydrolysis. It is noteworthy that for sugars containing sialic acid moieties, a protecting group must be used to stabilize sialic acid groups during sequential alkaline degradation. This described approach was applied to two high mannose oligosaccharides M5G2, M6G2 cleaved from the ribonuclease B and a complex oligosaccharide A2 cleaved from transferrin. T he amino acid sequence alone is generally insufficient to describe protein function. The biologically active forms of mature proteins are often post-translationally modified and these modifications typically influence protein function. Glycosylation is a predominant modification mechanism. It has been estimated that 60 -90% of all mammalian proteins are glycosylated [1]. The carbohydrate chains play critical roles in numerous biological processes, including fertilization, immune response, viral replication, parasitic inflection, cell-cell adherence, degradation of blood clots, and inflammation, for example [1][2][3][4]. The structural diversity inherent in the sugar moieties of a glycoprotein enables subtle changes in protein shape, charge, and volume, which can affect function both temporally and spatially. To achieve a full understanding of the function of a glycoprotein, a detailed characterization of its glycan structure is imperative.Structural elucidation of complex carbohydrates requires determination of monosaccharide composition, sequence, branching pattern, glycosidic linkages, and anomeric configuration. Nuclear magnetic resonance (NMR) comes close to providing complete structural analysis, although the amount of sample required and difficulty with analyzing complex mixtures limits the utility of NMR, particularly for proteomics applications. In recent years, mass spectrometry (MS) has become a key tool for structural analysis of carbohydrates. Several mass spectrometric techniques have been proved to be useful analytical tools for the determination of oligosaccharide structure. All of these techniques have the advantages over traditional methods [5], such as low sample consu...

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“…Recently, several studies have appeared in which excellent fragmentation of carbohydrates has been recorded with Q‐Tof instruments 15–23. However, these studies have all involved electrospray ionisation which tends to produce doubly or multiply charged ions whose fragmentation is usually less informative than that obtained from singly charged species 23.…”

mentioning

confidence: 99%

Ionisation and fragmentation of complex glycans with a quadrupole time‐of‐flight mass spectrometer fitted with a matrix‐assisted laser desorption/ionisation ion source

Harvey

Bateman

Bordoli

et al. 2000

Rapid Commun. Mass Spectrom.

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Profiling of 2-aminoacridone derivatised glycans by electrospray ionization mass spectrometry

Cited by 40 publications

References 14 publications

Evidence for linkage position determination in known feruloylated mono‐ and disaccharides using electrospray ion trap mass spectrometry

Evidence for linkage position determination in known feruloylated mono‐ and disaccharides using electrospray ion trap mass spectrometry

Linkage and branch determination of N-linked oligosaccharides using sequential degradation/closed-ring chromophore labeling/negative ion trap mass spectrometry

Ionisation and fragmentation of complex glycans with a quadrupole time‐of‐flight mass spectrometer fitted with a matrix‐assisted laser desorption/ionisation ion source

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