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Related Concept Videos

Mass Spectrometry: Molecular Fragmentation Overview01:20

Mass Spectrometry: Molecular Fragmentation Overview

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...
Radical Formation: Overview01:03

Radical Formation: Overview

A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the latter, also known...
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired molecule. These three...
Mass Spectrometry: Carboxylic Acid, Ester, and Amide Fragmentation01:01

Mass Spectrometry: Carboxylic Acid, Ester, and Amide Fragmentation

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 fragmentation of...
Mass Spectrometry: Cycloalkene Fragmentation00:54

Mass Spectrometry: Cycloalkene Fragmentation

The molecular ions of cycloalkenes undergo fragmentation via a retro-Diels–Alder reaction.
Radical Formation: Abstraction00:47

Radical Formation: Abstraction

The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
Even though homolysis produces radicals, it is different from radical...

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Resin-Assisted Capture Coupled with Isobaric Tandem Mass Tag Labeling for Multiplexed Quantification of Protein Thiol Oxidation
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The cysteine radical cation: structures and fragmentation pathways.

Junfang Zhao1, K W Michael Siu, Alan C Hopkinson

  • 1Department of Chemistry and Centre for Research in Mass Spectrometry, York University, 4700 Keele Street, Toronto, Ontario, Canada.

Physical Chemistry Chemical Physics : PCCP
|January 24, 2008
PubMed
Summary
This summary is machine-generated.

This study explores the cysteine radical cation, revealing a stable Captodative-1 isomer due to electron donation and acceptance. Isomerization pathways and fragmentation routes are also detailed.

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Area of Science:

  • Computational Chemistry
  • Theoretical Chemistry
  • Biomolecular Ion Chemistry

Background:

  • Cysteine is a crucial amino acid with diverse biological roles.
  • Understanding the reactivity of radical cations is vital for fields like mass spectrometry and radiation chemistry.
  • The initial electronic state and potential transformations of the cysteine radical cation remain areas of theoretical interest.

Purpose of the Study:

  • To theoretically investigate the structures, energies, and reaction pathways of the cysteine radical cation.
  • To identify the most stable isomer and elucidate its stabilizing features.
  • To map isomerization reactions and fragmentation pathways from the canonical radical cation.

Main Methods:

  • Utilized hybrid density functional theory (B3LYP) for calculations.
  • Employed the 6-311++G(d,p) basis set for high accuracy.
  • Analyzed relative energies, isomerization barriers, and fragmentation pathways.

Main Results:

  • Identified a global minimum isomer, Captodative-1, stabilized by a captodative effect (NH2 donor, C(OH)2+ acceptor).
  • Determined relative enthalpies for key isomers: Captodative-1, Distonic-S-1, and Distonic-C-1.
  • Calculated activation enthalpies for isomerization from the canonical form to Captodative-1 and Distonic-S-1, revealing a lower barrier to Distonic-S-1.

Conclusions:

  • The Captodative-1 isomer represents the most stable structure for the cysteine radical cation.
  • Isomerization to the sulfur-centered radical cation (Distonic-S-1) is kinetically accessible.
  • The study provides a comprehensive theoretical framework for understanding cysteine radical cation chemistry and fragmentation.