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The ionization of a molecule into a molecular ion inside the mass spectrometer causes instability in the molecule's structure due to the loss of an electron. This eventually leads to the fragmentation or breaking of some bonds in the molecule. The fragmentation occurs predominantly at specific bonds to yield relatively stable fragments.
One type of fragmentation pattern is the cleavage of a single bond in the molecular ion. The cleavage leads to a radical and a cation. The cleavage can occur at...
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The fragmentation patterns observed for compounds such as carboxylic acids, esters, and amides in the mass spectra include ⍺-cleavage and McLafferty rearrangement. Fragmentation by ⍺-cleavage preferentially occurs at the carbon-carbon bond at the ⍺-position next to the carboxylic group to generate a neutral radical and a cation. Long chain compounds with hydrogen at their γ-carbon undergo McLafferty rearrangement to give a radical cation and a neutral alkene.
For example, the...
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Mass Spectrometry: Long-Chain Alkane Fragmentation01:18

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The molecular ions of linear alkanes prefer to fragment at the carbon-carbon bond away from the end of the chain since the cleavage of an inner bond creates a stable carbocation and a stable radical. Consequently, the mass signals of linear alkanes feature intense peaks in the middle of the mass-to-charge ratio plot with weaker peaks on either end. The fragmentation of each carbon-carbon bond with the release of a methyl group in each splitting leads to prominent peaks in the mass spectra...
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In mass spectrometry, cycloalkanes exhibit distinct fragmentation patterns due to the inherent stability of their molecular ions compared to linear or branched alkanes. The ring structure of cycloalkanes provides additional stability to the molecular ions, often resulting in prominent ion peaks in the mass spectrum.
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The molecular ions of cycloalkenes undergo fragmentation via a retro-Diels–Alder reaction.
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Mass Spectrometry: Alkene Fragmentation00:59

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Alkenes lose one electron from the unsaturated π bond upon ionization and form stable molecular ions. Further fragmentation of alkenes occurs through three different reaction pathways. The most prominent fragmentation is the cleavage at the allylic position. The resultant allylic carbocation is resonance stabilized. In the mass spectra of terminal alkenes, this fragment appears at a mass-to-charge ratio of 41. In the internal alkenes, where there are two choices of allylic cleavage, the...
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Cationized Carbohydrate Gas-Phase Fragmentation Chemistry.

Benjamin J Bythell1, Maha T Abutokaikah2, Ashley R Wagoner2

  • 1Department of Chemistry and Biochemistry, University of Missouri, St. Louis, MO, 63121, USA. bythellb@umsl.edu.

Journal of the American Society for Mass Spectrometry
|November 30, 2016
PubMed
Summary

This study reveals key fragmentation pathways in cationized D-lactose using mass spectrometry and computation. Findings clarify glycosidic bond cleavage and cross-ring fragmentation mechanisms, refining carbohydrate analysis.

Keywords:
Collision-induced dissociationDensity functional theoryGlycansIon structureLabelingMass spectrometryMetals

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Area of Science:

  • Analytical Chemistry
  • Carbohydrate Chemistry
  • Computational Chemistry

Background:

  • Understanding carbohydrate fragmentation is crucial for structural elucidation.
  • Cationization significantly influences dissociation pathways in mass spectrometry.
  • Previous models for D-lactose fragmentation require refinement.

Purpose of the Study:

  • To investigate the fragmentation chemistry of cationized D-lactose.
  • To elucidate the mechanisms of glycosidic bond cleavage and cross-ring cleavages.
  • To compare fragmentation patterns across different cation types (proton, sodium).

Main Methods:

  • Tandem mass spectrometry (MS/MS)
  • Regioselective labeling
  • Computational chemistry (density functional theory)
  • Analysis of D-lactose fragmentation

Main Results:

  • Energetically favorable conformations of cationized D-lactose are similar.
  • Glycosidic bond cleavage proceeds via protonation of the glycosidic oxygen.
  • Calculations support sodiated 1,6-anhydrogalactose B_n ion structures for sodiated D-lactose.
  • Low-energy cross-ring cleavages occur via a retro-aldol mechanism in metal-cationized forms.
  • Consecutive fragmentation processes are important, especially for protonated species.

Conclusions:

  • The study provides a detailed mechanistic understanding of D-lactose fragmentation.
  • Results challenge previous proposals regarding B_n-Y_m fragmentation pathways.
  • The findings impact the prediction of fragmentation branching ratios.
  • Anomeric configuration influences fragmentation energies but not overall ranking.