A New Example of Rearrangement Observed in the Tandem Mass Spectra of Oligosaccharides

Chizhov, Alexander O.; Filatov, Andrei V.; Perepelov, Andrei V.; Knirel, Yuriy A.

doi:10.1134/s1061934820140075

Cited by 2 publications

(3 citation statements)

References 9 publications

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“…On the downside, documentation regarding the possible rearrangements occurring on Li + or Na + species is scarce, but such reports are increasing in the recent literature. For instance, Bythell and co-workers recently investigated the fragmentation pathways of alkali-cationized oligosaccharides using the Fafoom genetic algorithm and Density Functional Theory. , It is also notable that gas-phase rearrangements of oligosaccharides that were previously considered impossible on alkali adducts, such as subunit migration and internal residue loss, were recently described for such ions . This questions whether other rearrangements described for protonated species can occur.…”

Section: Introductionmentioning

confidence: 99%

“…40,41 It is also notable that gasphase rearrangements of oligosaccharides that were previously considered impossible on alkali adducts, such as subunit migration and internal residue loss, were recently described for such ions. 42 This questions whether other rearrangements described for protonated species can occur. For example, pyranose-to-furanose isomerization was recently evidenced in protonated peptidoglycans.…”

Section: ■ Introductionmentioning

confidence: 99%

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Gas-Phase Behavior of Galactofuranosides upon Collisional Fragmentation: A Multistage High-Resolution Ion Mobility Study

Ollivier

Legentil

Yeni

et al. 2023

J. Am. Soc. Mass Spectrom.

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Carbohydrates are ubiquitous in nature but are among the least conserved biomolecules in life. These biopolymers pose a particular challenge to analytical chemists because of their high diversity and structural heterogeneity. In addition, they contain many isomerisms that complicate their structural characterization, notably by mass spectrometry. The tautomerism of the constitutive subunits is of particular interest. A given cyclized monosaccharide unit can take two forms: a most common 6membered ring (pyranose, p) and a more flexible 5-membered ring (furanose, f). The tautomers impact the biological properties of polysaccharides, resulting in interesting properties of the derived oligosaccharides. From an analytical point of view, the impact of tautomerism on the gas-phase behavior of ions has scarcely been described in the literature. In this work, we study the behavior of Galf-containing oligosaccharides, ionized as [M+Li] + species, under collisional dissociation (CID) conditions using high-resolution and multistage ion mobility (IMS) on a Cyclic IMS platform. In the first part of this work, we studied whether disaccharidic fragments released from Galf-containing (Gal) 1 (Man) 2 trisaccharides (and their Galp counterpart) would match the corresponding disaccharide standards, and�despite the fragments generally being a good match�we showed the possibility of Galf migrations and other unidentified alterations in the IMS profile. Next, we expanded on these unknown features using multistage IMS and molecular dynamics, unveiling the contributions of additional gas-phase conformers in the profile of fragments from a Galf-containing trisaccharide compared with the corresponding disaccharides.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Gas-Phase Behavior of Galactofuranosides upon Collisional Fragmentation: A Multistage High-Resolution Ion Mobility Study

Ollivier

Legentil

Yeni

et al. 2023

J. Am. Soc. Mass Spectrom.

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“…Although, as stated above, it is generally believed that internal residue losses such as those caused by fucose migration, are restricted to [M + H] + ions, a paper by Chizhov et al (2020) have reported that the internal rhamnose residue can be eliminated from both the [M + H] + and [M + Na] + ions from compound 160 (Scheme 9) under CID conditions. No similar elimination was observed from the [M – H] ‐ ion.…”

Section: Fragmentationmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2019–2020

Harvey

2023

Mass Spectrometry Reviews

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This review is the tenth update of the original article published in 1999 on the application of matrix‐assisted laser desorption/ionization (MALDI) mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2020. Also included are papers that describe methods appropriate to analysis by MALDI, such as sample preparation techniques, even though the ionization method is not MALDI. The review is basically divided into three sections: (1) general aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, fragmentation, quantification and the use of arrays. (2) Applications to various structural types such as oligo‐ and polysaccharides, glycoproteins, glycolipids, glycosides and biopharmaceuticals, and (3) other areas such as medicine, industrial processes and glycan synthesis where MALDI is extensively used. Much of the material relating to applications is presented in tabular form. The reported work shows increasing use of incorporation of new techniques such as ion mobility and the enormous impact that MALDI imaging is having. MALDI, although invented nearly 40 years ago is still an ideal technique for carbohydrate analysis and advancements in the technique and range of applications show little sign of diminishing.

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A New Example of Rearrangement Observed in the Tandem Mass Spectra of Oligosaccharides

Cited by 2 publications

References 9 publications

Gas-Phase Behavior of Galactofuranosides upon Collisional Fragmentation: A Multistage High-Resolution Ion Mobility Study

Gas-Phase Behavior of Galactofuranosides upon Collisional Fragmentation: A Multistage High-Resolution Ion Mobility Study

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2019–2020

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