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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...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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...

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Related Experiment Video

Updated: May 15, 2026

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

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

Published on: May 15, 2012

A general solid phase method for the synthesis of depsipeptides.

Mary M Nguyen1, Nicole Ong, Laura Suggs

  • 1The University of Texas at Austin, Department of Biomedical Engineering, 107 W Dean Keeton Street, Austin, TX 78712, USA. m.nguyen@utexas.edu

Organic & Biomolecular Chemistry
|January 12, 2013
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel depsipeptide sequences with alternating ester and amide backbones using a protected depsidipeptide building block. The Fmoc/tBu solid-phase peptide synthesis (SPPS) strategy proved most effective for this unique peptide backbone construction.

More Related Videos

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
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An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity

Published on: November 2, 2016

An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis
06:19

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

Published on: November 22, 2024

Related Experiment Videos

Last Updated: May 15, 2026

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

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

Published on: May 15, 2012

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
12:02

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity

Published on: November 2, 2016

An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis
06:19

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

Published on: November 22, 2024

Area of Science:

  • Organic Chemistry
  • Polymer Chemistry
  • Biochemistry

Background:

  • Peptides are crucial biomolecules with diverse functions.
  • Traditional peptide synthesis focuses on amide bonds.
  • Depsipeptides, containing ester linkages, offer unique structural and functional properties.

Purpose of the Study:

  • To develop a robust method for synthesizing depsipeptide sequences with alternating ester and amide bonds.
  • To establish a versatile building block strategy for complex depsipeptide assembly.
  • To evaluate different solid-phase peptide synthesis (SPPS) conditions for compatibility.

Main Methods:

  • Synthesis of a protected depsidipeptide building block.
  • Manual solid-phase peptide synthesis (SPPS) using the depsidipeptide unit.
  • Exploration of Fmoc/OBzl and Fmoc/tBu SPPS strategies.

Main Results:

  • Successful synthesis of depsipeptide sequences with alternating ester and amide linkages.
  • Identification of the Fmoc/tBu SPPS strategy as optimal for the methodology.
  • Demonstration of a building block approach for depsipeptide synthesis.

Conclusions:

  • The developed methodology enables the construction of novel depsipeptide backbones.
  • The Fmoc/tBu SPPS strategy is highly compatible with this novel synthesis approach.
  • This work provides a foundation for creating new classes of peptide-based materials and therapeutics.