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Related Concept Videos

Preparation of Amides01:29

Preparation of Amides

3.3K
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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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.9K
Peptidoglycan Synthesis01:28

Peptidoglycan Synthesis

752
Structure of PeptidoglycanPeptidoglycan is a vital structural component of the bacterial cell wall, providing mechanical strength and shape to the cell. It consists of repeating units of two sugars—N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM)—linked by β-1,4 glycosidic bonds. These sugar chains are cross-linked by short peptide chains, forming a mesh-like polymer that surrounds the bacterial plasma membrane.Cytoplasmic Phase – Precursor SynthesisPeptidoglycan...
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Related Experiment Video

Updated: Oct 18, 2025

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Three Methods for the Solution Phase Synthesis of Cyclic Peptides.

Angelika Ullrich1, Lukas Junk2, Uli Kazmaier2

  • 1Organic Chemistry, Saarland University, Saarbrücken, Germany. a.ullrich@mx.uni-saarland.de.

Methods in Molecular Biology (Clifton, N.J.)
|October 1, 2021
PubMed
Summary

Efficient cyclization of linear peptides into cyclic peptides is crucial for their biological applications. This study presents three novel amide bond formation protocols for peptide and depsipeptide macrolactamization, applicable to diverse peptide sequences.

Keywords:
CyclodepsipeptidesCyclopeptidesMacrocyclization of peptidesMacrolactamizationPeptide coupling

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Biochemistry

Background:

  • Cyclic peptides possess significant biological properties, making them valuable therapeutic candidates.
  • Efficient synthesis of cyclic peptides is essential for drug discovery and development.
  • Macrolactamization of linear peptide precursors is a key strategy for cyclic peptide formation.

Purpose of the Study:

  • To develop and present novel, efficient protocols for the cyclization of peptides and depsipeptides.
  • To demonstrate the versatility of these methods for various linear peptide sequences.
  • To facilitate the synthesis of cyclic peptides with potential biological applications.

Main Methods:

  • Development of three distinct protocols for amide bond formation.
  • Application of macrolactamization techniques to protected linear peptide and depsipeptide chains.
  • Optimization of reaction conditions for efficient cyclization.

Main Results:

  • Successful cyclization of peptides and depsipeptides was achieved using the developed protocols.
  • The presented methods demonstrated broad applicability to different linear peptide structures.
  • High yields and purity of cyclic products were obtained.

Conclusions:

  • The described amide bond formation protocols offer efficient and versatile routes to cyclic peptides.
  • These methods are valuable tools for synthetic chemists and drug discovery programs.
  • The developed cyclization strategies can be applied to a wide range of linear peptide substrates.