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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

7.6K
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.
7.6K
Alkyl Halides02:45

Alkyl Halides

20.2K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
20.2K
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

5.8K
Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
5.8K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

12.3K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
12.3K
Mass Spectrometry: Alkyl Halide Fragmentation01:22

Mass Spectrometry: Alkyl Halide Fragmentation

1.6K
Chlorine isotopes exist as 35Cl and 37Cl in a 3:1 ratio, while bromine isotopes exist as 79Br and 81Br in a 1:1 ratio. The mass spectrum of alkyl halides typically produces two distinct molecular ion peaks, the molecular ion peak, [M], and the molecular ion plus two, [M + 2] peak. The relative heights of these two peaks are proportional to the isotopic abundance ratios of the halide. For example, 2‐chloropropane and 1‐bromopropane display two peaks with relative peak heights in a 3:1 and...
1.6K
Conversion of Alcohols to Alkyl Halides02:48

Conversion of Alcohols to Alkyl Halides

8.5K
This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...
8.5K

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Related Experiment Video

Updated: Feb 14, 2026

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

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Bioconjugation through Mesitylene Thiol Alkylation.

Iván Ramos-Tomillero1,2, Gema Perez-Chacon3, Beatriz Somovilla-Crespo4

  • 1Institute for Research in Biomedicine , 08028 - Barcelona , Spain.

Bioconjugate Chemistry
|February 14, 2018
PubMed
Summary
This summary is machine-generated.

Researchers developed a new mesitylene scaffold linker for bioconjugation, enhancing antibody drug conjugate preparation. This method efficiently links antibodies, preserving their integrity and binding affinity for therapeutic applications.

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Area of Science:

  • Macromolecular chemistry
  • Bioconjugation chemistry
  • Immunoconjugation

Background:

  • Bioconjugation is crucial for developing therapeutic conjugates.
  • Efficient, selective, and safe conjugation methods are needed.
  • Antibody drug conjugates (ADCs) show therapeutic promise.

Purpose of the Study:

  • To evaluate a bis(bromomethyl)benzene scaffold as a linker for bioconjugation.
  • To specifically assess its utility in antibody conjugation.
  • To develop a method for creating antibody drug conjugates.

Main Methods:

  • Monothioalkylation of 1,3,5-tris(bromomethyl)benzene to create reactive derivatives.
  • Thiol bis-alkylation using bis(Cys)-containing peptides or antibodies.
  • Partial reduction of antibody disulfide bonds prior to conjugation.
  • Characterization using mass spectrometry, UV-vis spectroscopy, and SDS-PAGE.
  • Assessment of antibody-antigen binding affinity via flow cytometry.

Main Results:

  • The mesitylene scaffold effectively linked peptides and monoclonal antibodies (anti-CD4, anti-CD13).
  • Conjugation preserved antibody integrity and antigen-binding capabilities.
  • Analytical techniques confirmed successful bioconjugation and linker performance.

Conclusions:

  • The mesitylene scaffold is a suitable linker for thiol-based bioconjugation.
  • This method shows potential for future antibody drug conjugate preparation.
  • The developed linker offers a promising approach for creating novel therapeutic macromolecules.