Radical mediated dissection of oligosaccharides

Zhang, Xing; Julian, Ryan R.

doi:10.1016/j.ijms.2014.07.045

Cited by 19 publications

(36 citation statements)

References 25 publications

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“…Oligosaccharide radical ions can also be generated by photodissociation of iodide derivatives. Zhang and Julian [49] covalently or noncovalently attached a radical-generating reagent to an oligosaccharide ion, and a radical can be generated by homolytic bond cleavage of specific carboniodine bonds in protonated systems by UVPD followed by radical transfer from the reagent to the analyte. Subsequent activation of the radical species generates information-rich spectra including a variety of cross-ring fragments.…”

Section: Radical Reaction Of Oligosaccharidesmentioning

confidence: 99%

Radical Reactions in the Gas Phase: Recent Development and Application in Biomolecules

Gao

Zhou

et al. 2014

Journal of Spectroscopy

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This review summarizes recent literature describing the use of gas phase radical reactions for structural characterization of complex biomolecules other than peptides. Specifically, chemical derivatization, in-source chemical reaction, and gas phase ion/ion reactions have been demonstrated as effective ways to generate radical precursor ions that yield structural informative fragments complementary to those from conventional collision-induced dissociation (CID). Radical driven dissociation has been applied to a variety of biomolecules including peptides, nucleic acids, carbohydrates, and phospholipids. The majority of the molecules discussed in this review see limited fragmentation from conventional CID, and the gas phase radical reactions open up completely new dissociation channels for these molecules and therefore yield high fidelity confirmation of the structures of the target molecules. Due to the extensively studied peptide fragmentation, this review focuses only on nonpeptide biomolecules such as nucleic acids, carbohydrates, and phospholipids.

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Section: Radical Reaction Of Oligosaccharidesmentioning

confidence: 99%

Radical Reactions in the Gas Phase: Recent Development and Application in Biomolecules

Gao

Zhou

et al. 2014

Journal of Spectroscopy

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“…Recently, free radical chemistry 46 has regained great attention in the field of biomolecular characterization. [47][48][49][50][51] Inspired by the achievement of electron activated dissociation (ExD) for glycan structure analysis, which usually involve fragmentation via low energy free radical dissociation pathways, we recently developed a novel free radical activation glycan sequencing reagent (FRAGS), along with a methylated free radical activated glycan sequencing reagent (Me-FRAGS) for glycan structural characterization. 26,52 Free radical-directed systematic glycan dissociation with high fragmentation efficiency has been obtained using these two free radical reagents.…”

Section: Introductionmentioning

confidence: 99%

“…However, such approaches require special instrumentation to allow for interaction of an electron source with targeted ions. Recently, free radical chemistry has regained great attention in the field of biomolecular characterization. − …”

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confidence: 99%

Resin and Magnetic Nanoparticle-Based Free Radical Probes for Glycan Capture, Isolation, and Structural Characterization

et al. 2019

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By combing the merits of solid supports and free radical activated glycan sequencing (FRAGS) reagents, we develop a multi-functional solid-supported free radical probe (SS-FRAGS), which enables glycan enrichment and characterization. SS-FRAGS comprises a solid support, free radical precursor, disulfide bond, pyridyl, and hydrazine moieties. Thioactivated resin and magnetic nanoparticles (MNPs) are chosen as the solid support to selectively capture free glycans via the hydrazine moiety, allowing for their enrichment and isolation. The disulfide bond acts as a temporary covalent linkage between the solid support and the captured glycan, allowing the release of glycans via the cleavage of the disulfide bond by dithiothreitol. The basic pyridyl functional group provides a site for the formation of a fixed charge, enabling detection by mass spectrometry and avoiding glycan rearrangement during collisional activation. The free radical precursor generates a nascent free radical upon collisional activation and thus simultaneously induces systematic and predictable fragmentation for glycan structure elucidation. A radical-driven glycan deconstruction diagram (R-DECON) is developed to visually summarize the MS 2 results and thus allow for the assembly of the glycan skeleton, making the differentiation of isobaric glycan isomers unambiguous. For application to a real-world sample, we demonstrate the efficacy of the SS-FRAGS by analyzing glycan structures enzymatically cleaved from RNase-B.

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“…Cold-ion infrared spectroscopy can be used for vibrational fingerprinting, , which can distinguish even the most similar compositional isomers, but the method also requires specialized equipment that is not widely available . Radical chemistry has also found utility in glycan characterization. − The Beauchamp group , reported excellent radical-based structural probing in conjunction with collisional activation, which also exhibited promising results for discrimination of several glycan isomers. These advances, and others, have positioned MS at the center of glycan profiling efforts even though complete characterization of all isomeric possibilities remains challenging …”

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confidence: 99%

Glycan Isomer Identification Using Ultraviolet Photodissociation Initiated Radical Chemistry

et al. 2018

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Glycans are fundamental biological macromolecules, yet despite their prevalence and recognized importance, a number of unique challenges hinder routine characterization. The multiplicity of OH groups in glycan monomers easily afford branched structures and alternate linkage sites, which can result in isomeric structures that differ by minute details. Herein, radical chemistry is employed in conjunction with mass spectrometry to enable rapid, accurate, and high throughput identification of a challenging series of closely related glycan isomers. The results are compared with analysis by collision-induced dissociation, higher-energy collisional dissociation, and ultraviolet photodissociation (UVPD) at 213 nm. In general, collision-based activation struggles to produce characteristic fragmentation patterns, while UVPD and radical-directed dissociation (RDD) can distinguish all isomers. In the case of RDD, structural differentiation derives from radical mobility and subsequent fragmentation. For glycans, the energetic landscape for radical migration is flat, increasing the importance of the three-dimensional structure. RDD is therefore a powerful and straightforward method for characterizing glycan isomers.

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Radical mediated dissection of oligosaccharides

Cited by 19 publications

References 25 publications

Radical Reactions in the Gas Phase: Recent Development and Application in Biomolecules

Radical Reactions in the Gas Phase: Recent Development and Application in Biomolecules

Resin and Magnetic Nanoparticle-Based Free Radical Probes for Glycan Capture, Isolation, and Structural Characterization

Glycan Isomer Identification Using Ultraviolet Photodissociation Initiated Radical Chemistry

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