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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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Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

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Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...
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Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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Peptide Bonds02:43

Peptide Bonds

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A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...
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Preparation of Amides01:29

Preparation of Amides

3.2K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Related Experiment Video

Updated: Aug 24, 2025

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center.

Chunli Song1, Zhanfeng Hou2, Zijun Jiao1

  • 1Pingshan Translational Medicine Center, Shenzhen Bay Laboratory.

Journal of Visualized Experiments : Jove
|October 24, 2022
PubMed
Summary
This summary is machine-generated.

This study presents an efficient method for synthesizing cyclic peptides using on-resin bisalkylation. This approach utilizes cysteine and methionine for novel cyclic peptide drug discovery applications.

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis

Background:

  • Cyclic peptides are gaining prominence in drug discovery due to their potent biological activities and clinical applications.
  • Developing efficient synthesis strategies is crucial for expanding the use of cyclic peptides in medicine.

Purpose of the Study:

  • To report a detailed and efficient protocol for synthesizing cyclic peptides.
  • To establish a robust method for cyclic peptide generation via bisalkylation.

Main Methods:

  • Solid-phase peptide synthesis was employed, coupling cysteine (Cys) and methionine (Met) simultaneously.
  • Cyclic peptides were formed through on-resin or intramolecular bisalkylation between Met and Cys using a tunable tether and sulfonium center.
  • A propargyl group on Met initiated thiol-yne addition for cyclization, followed by purification via HPLC and characterization using LC-MS and 1H NMR.

Main Results:

  • An efficient three-step protocol was developed for cyclic peptide synthesis: Cys deprotection, linker coupling, and Cys-Met cyclization.
  • The method demonstrated successful synthesis of cyclic peptides via bisalkylation and thiol-yne addition.
  • Characterization confirmed the molecular weight and stability of the synthesized cyclic peptides.

Conclusions:

  • The developed protocol offers an effective strategy for the efficient synthesis of cyclic peptides.
  • This method facilitates the advancement of cyclic peptides in drug discovery and clinical applications.