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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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The molecular ion peak of a molecule in the mass spectrum provides vital information for molecular identification. However, conventional electron impact ionization can lead to the rapid dissociation of some molecular ions before they reach the detector. A milder ionization method is required to increase the lifetime of such ionized analyte molecules. Chemical ionization (CI) is a gas-phase protonation reaction useful for mass-analyzing analyte molecules that are easily protonated to yield the...
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SN2 Reaction: Stereochemistry02:23

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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E1 Reaction: Kinetics and Mechanism02:46

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Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only...
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Reference-free thio-succinimide isomerization characterization by electron-activated dissociation.

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This study introduces a novel method to differentiate thio-succinimide hydrolysis isomers in antibody-drug conjugates (ADCs). The technique uses mass spectrometry to identify specific product ions, aiding ADC development.

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Area of Science:

  • Pharmaceutical Chemistry
  • Analytical Chemistry
  • Bioconjugation Chemistry

Background:

  • Isomerism is critical in pharmaceutical development, influencing drug pharmacology and molecular design.
  • Thio-succinimide hydrolysis in antibody-drug conjugates (ADCs) generates constitutional isomers: thio-aspartyl and thio-isoaspartyl.
  • Differentiating these isomers is essential for understanding ADC stability and efficacy.

Purpose of the Study:

  • To develop and validate a novel method for differentiating thio-succinimide hydrolysis isomers.
  • To investigate the isomerization process of thio-succinimide linkages in ADCs over time in plasma.
  • To establish a reliable approach for isomer identification without reference standards.

Main Methods:

  • A hybrid approach combining ligand binding assay (LBA) and liquid chromatography-tandem mass spectrometry (LC-MS/MS).
  • Utilized two orthogonal dissociation methods: collision-induced dissociation (CID) and electron-activated dissociation (EAD).
  • Analyzed MS/MS spectra generated by CID and EAD to identify unique isomer signatures.

Main Results:

  • Distinct MS/MS spectra were observed for thio-aspartyl and thio-isoaspartyl isomers using EAD.
  • Identified signature product ions, including [R1 + Thio + 57 + H]+, [R2 + Succ + H2O - 57 + H]+, and [R2 + Succ + H2O - 44 + 2H]2+.
  • A newly discovered [R2 + ThioSucc + H2O - 44 + 2H]2+ ion provided further evidence for isomer differentiation.

Conclusions:

  • Successfully identified thio-succinimide hydrolysis isomers without synthesized reference materials.
  • The developed method is applicable to various thio-succinimide-linked molecules.
  • Accurate isomer identification will advance the development and application of ADCs.