Infrared Multiphoton Dissociation of O-Linked Mucin-Type Oligosaccharides

Zhang, Jinhua; Schubothe, Katherine M.; Li, Bensheng; Russell, Scott C.; Lebrilla, Carlito B.

doi:10.1021/ac0489824

Cited by 72 publications

(97 citation statements)

References 56 publications

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“…Several lower molecular weight glycosidic and cross-ring cleavage product ions were observed only following IRMPD. Although IRMPD and lowenergy CAD are both low-energy vibrational excitation techniques, Lebrilla and coworkers have shown that the fragmentation efficiency in IRMPD is greater than that in CAD for larger oligosaccharides [56]. An alternative explanation for the absence of low molecular weight species following CAD is the time-of-flight effect when transferring ions from the external hexapole to the ICR cell.…”

Section: Ms/ms Of Neutral Oligosaccharidesmentioning

confidence: 99%

Electron detachment dissociation of neutral and sialylated oligosaccharides

Adamson

Håkansson

2007

J. Am. Soc. Mass Spectrom.

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Electron detachment dissociation (EDD) has recently been shown by Amster and coworkers to constitute a valuable analytical approach for structural characterization of glycosaminoglycans. Here, we extend the application of EDD to neutral and sialylated oligosaccharides. Both branched and linear structures are examined, to determine whether branching has an effect on EDD fragmentation behavior. EDD spectra are compared to collisional activated dissociation (CAD) and infrared multiphoton dissociation (IRMPD) spectra of the doubly and singly deprotonated species. Our results demonstrate that EDD of both neutral and sialylated oligosaccharides provides structural information that is complementary to that obtained from both CAD and IRMPD. In all cases, EDD resulted in additional cross-ring cleavages. In most cases, cross-ring fragmentation obtained by EDD is more extensive than that obtained from IRMPD or CAD. Our results also indicate that branching does not affect EDD fragmentation, contrary to what has been observed for electron capture dissociation (ECD). . Unlike most biomolecules, oligosaccharides often exist as several isomeric forms with diverse linkages, and may form linear or branched structures. Complete structural characterization of oligosaccharides requires the determination of constituent monosaccharides, their linkage, sequence, and branching patterns. Given their diversity and structural complexity, structural elucidation of oligosaccharides often relies upon a wide range of analytical methodologies, of which nuclear magnetic resonance spectroscopy and mass spectrometry are two vital techniques. Tandem mass spectrometry (MS/MS) is widely used for glycan structural characterization [5][6][7], due to the advent of instruments that provide high-quality spectra from even low-abundance molecular species.Tandem mass spectra of oligosaccharides consist mainly of glycosidic and cross-ring product ions. Glycosidic cleavage occurs between monosaccharide units and provides information regarding saccharide sequence and branching. Cross-ring cleavages can provide valuable information regarding saccharide linkage, particularly when occurring at branching residues. Several factors are known to affect oligosaccharide fragmentation and the degree of cross-ring fragmentation, such as the ionizing cation, the lifetime of the ion before detection, and the energy deposited into the ion.Typically, neutral oligosaccharides are analyzed in positive-ion mode, by their protonated forms or through metal ion adduction. In addition, chemical derivatization such as permethylation is widely used to increase sensitivity, reduce molecular ion lability, and produce structurally diagnostic product ions [8 -10]. Low-energy activation methods, such as collisional activated dissociation (CAD) and infrared multiphoton dissociation (IRMPD), applied to protonated oligosaccharides results in predominantly glycosidic cleavages. However, oligosaccharides ionized with alkali, alkaline earth, and transition metals often fragment to yield more cro...

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Section: Ms/ms Of Neutral Oligosaccharidesmentioning

confidence: 99%

Electron detachment dissociation of neutral and sialylated oligosaccharides

Adamson

Håkansson

2007

J. Am. Soc. Mass Spectrom.

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“…Alternatively, other activation techniques have been used for the structural characterization of glycans, including infrared multiphoton dissociation (IRMPD) [40 -43] and electron capture dissociation (ECD) [44,45]. Although IRMPD and CID are both low-energy vibrational excitation techniques, Lebrilla and coworkers [42] have shown that the fragmentation efficiency of IRMPD increases with increasing oligosaccharide size. Recent efforts in the fragmentation of various metal-cationized oligosaccharides by ECD have provided structural information complementary to IRMPD [45].…”

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confidence: 99%

Identification of isomeric N-glycan structures by mass spectrometry with 157 nm laser-induced photofragmentation

Devakumar

Mechref

Kang

et al. 2008

J. Am. Soc. Mass Spectrom.

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Characterization of structural isomers has become increasingly important and extremely challenging in glycobiology. This communication demonstrates the capability of ion-trap mass spectrometry in conjunction with 157 nm photofragmentation to identify different structural isomers of permethylated N-glycans derived from ovalbumin without chromatographic separation. The results are compared with collision-induced dissociation (CID) experiments. Photodissociation generates extensive cross-ring fragment ions as well as diagnostic glycosidic product ions that are not usually observed in CID MS/MS experiments. The detection of these product ions aids in characterizing indigenous glycan isomers. The ion trap facilitates MS n experiments on the diagnostic glycosidic fragments and cross-ring product ions generated through photofragmentation, thus allowing unambiguous assignment of all of the isomeric structures associated with the model glycoprotein used in this study. Photofragmentation is demonstrated to be a powerful technique for the structural characterization of glycans. , and protein regulations and interactions [6], is widely acknowledged [7]. To improve our understanding of these processes, it is important to explore glycan structure-function relationships. However, the detailed characterization of a glycan structure and its attributes remains a difficult task, given the microheterogeneity and diversity of these molecules. Importantly, the discrimination of numerous structural isomers differing in sequence, linkage, position, or branching features remains a challenging frontier of glycobiology.For years, the characterization of glycan structures has almost exclusively been accomplished by tandem mass spectrometry (MS/MS) [1,8,9] because of its high sensitivity and minimum sample requirements relative to nuclear magnetic resonance (NMR). Different combinations of ionization techniques, ion activation, and A glycan ion generally fragments in two ways: (1) glycosidic cleavages resulting from a bond rupture between two adjacent sugar residues and (2) cross-ring cleavages in which any two bonds on the same sugar unit are broken. Cross-ring fragment ions are commonly observed in high-energy collision-induced dissociation (CID) methods as demonstrated in the tandem TOF/TOF approach [34 -38]. A limitation of this technique, however, is its inability to perform multistage tandem mass spectrometry experiments. On the other hand, glycosidic cleavage ions are predominantly observed in low-energy activation methods and are mainly used to derive sequence and limited branching information. Most recently, demonstrated the use of low-energy activation to identify the structural isomers of glycans in complex mixtures with the help of sequential tandem mass spectrometry (MS n ). However, a disadvantage of CID is the decrease in both the degree and efficiency of dissociation with increasing mass and MS n events. Alternatively, other activation techniques have been used for Address reprint requests to Prof. James P.

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“…As the low-energy CID in the IT analyzers [32,34,44] or the PSD in MALDI/TOF MS instruments [45] is generally insufficient to accomplish this fragmentation task, we have chosen a MALDI/TOF/TOF MS with high-energy CID capabilities to furnish extensive fragmentation of model neutral [46][47][48][49][50] and acidic [46,51] glycans. An alternative approach pursued elsewhere for extensive fragmentation of glycans involves Fourier transform ion cyclotron resonance MS used in conjunction with sustained offresonance irradiation (SORI) [52], CID [52,53], IR multiphoton dissociation (IRMPD) [54][55][56], or electron capture dissociation (ECD) [54,55]. In our MALDI/TOF/TOF MS experiments, we were able to distinguish a subtle form of isomerism in the mannose-rich glycans [47] (Fig.…”

Section: Capillary Lc/maldi/tof/tof Ms: a Platform For Functional-glymentioning

confidence: 92%

New hyphenated methodologies in high‐sensitivity glycoprotein analysis

Novotný

Mechref

2005

J of Separation Science

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High-sensitivity glycoprotein analyses are of particular interest in modern biomedical and clinical research, as well as in the development of recombinant protein products. The evolution of new hyphenated methodologies in high-sensitivity glycoprotein analysis is highlighted in this thematic review. These methodologies include, in particular, capillary LC/MALDI/TOF/TOF MS in conjunction with online permethylation platform, and silica-based lectin microcolumns interfaced to MS. The potential of these methodologies in glycomic and glycoproteomic analysis is demonstrated for model glycoproteins as well as total glycomes and glycoproteomes derived from biological samples. Additionally, the applications of CE-MS, CEC, and nanoLC with graphitized carbon in the areas of glycomics and glycoproteomics are described.

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Infrared Multiphoton Dissociation of O-Linked Mucin-Type Oligosaccharides

Cited by 72 publications

References 56 publications

Electron detachment dissociation of neutral and sialylated oligosaccharides

Electron detachment dissociation of neutral and sialylated oligosaccharides

Identification of isomeric N-glycan structures by mass spectrometry with 157 nm laser-induced photofragmentation

New hyphenated methodologies in high‐sensitivity glycoprotein analysis

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