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Related Concept Videos

Preparation of Amides01:29

Preparation of Amides

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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Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
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Published on: May 15, 2012

The depsipeptide method for solid-phase synthesis of difficult peptides.

Irene Coin1

  • 1The Salk Institute for Biological Studies, CBPL, La Jolla, CA 92037-1099, USA. icoin@salk.edu

Journal of Peptide Science : an Official Publication of the European Peptide Society
|April 20, 2010
PubMed
Summary
This summary is machine-generated.

Chemists can now synthesize difficult peptides and proteins using the novel depsipeptide method. This ester-based approach overcomes folding and aggregation issues, improving accessibility of complex biomolecules.

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Last Updated: Jun 13, 2026

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
11:42

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Published on: May 15, 2012

An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis
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Area of Science:

  • Chemical synthesis
  • Peptide chemistry
  • Biomolecular synthesis

Background:

  • Peptide and protein synthesis face limitations due to folding and aggregation.
  • Short, biologically relevant peptides like beta-amyloid can form aggregates or complex structures.
  • These challenges hinder the accessibility of many important biomolecules via traditional chemosynthesis.

Purpose of the Study:

  • To introduce and evaluate the depsipeptide method for synthesizing difficult peptide sequences.
  • To demonstrate the utility of O-acyl isopeptides as intermediates in peptide assembly.
  • To explore optimization strategies and efficiency of the depsipeptide approach.

Main Methods:

  • Utilizing depsipeptides (O-acyl isopeptides) as ester isomers for easier assembly and purification.
  • Applying mild conditions for the conversion of depsipeptides to the target peptide amides.
  • Investigating the chemical aspects and optimization steps of the depsipeptide method.

Main Results:

  • The depsipeptide method facilitates the synthesis of peptides prone to folding and aggregation.
  • This technique is effective for sequences containing serine or threonine residues.
  • The conversion to parent amides is efficient under mild conditions, yielding improved outcomes.

Conclusions:

  • The depsipeptide method offers a significant advancement in overcoming challenges in peptide and protein chemosynthesis.
  • It provides a viable strategy for producing difficult sequences that were previously inaccessible.
  • Analogous principles may be applied to peptide segment condensation and cyclodepsipeptide synthesis.