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Related Concept Videos

Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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 23, 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

Simple and efficient solid-phase preparation of azido-peptides.

Morten B Hansen1, Theodorus H M van Gurp, Jan C M van Hest

  • 1Radboud University, Institute for Molecules and Materials, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.

Organic Letters
|April 18, 2012
PubMed
Summary

A novel diazotransfer reagent, imidazole-1-sulfonyl azide hydrochloride, efficiently converts peptide N-termini to azides. This rapid, high-yield reaction occurs under mild aqueous or DMF conditions on solid-phase resins.

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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
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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

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Last Updated: May 23, 2026

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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
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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

Area of Science:

  • Organic Chemistry
  • Peptide Chemistry
  • Synthetic Methodology

Background:

  • Solid-phase peptide synthesis (SPPS) is a cornerstone of modern biochemistry.
  • Introducing azide functionalities is crucial for bioconjugation and further synthetic transformations.
  • Existing diazotransfer reagents can suffer from instability or require harsh reaction conditions.

Purpose of the Study:

  • To introduce a stable and readily accessible diazotransfer reagent for peptide modification.
  • To demonstrate the efficient conversion of a peptide N-terminus to an azide moiety on solid phase.
  • To evaluate the reagent's performance under various solid-phase synthesis conditions.

Main Methods:

  • Utilized imidazole-1-sulfonyl azide hydrochloride as the diazotransfer reagent.
  • Performed the N-terminal transformation on a model peptide immobilized on NovaPEG resin (aqueous conditions) and polystyrene beads (DMF).
  • Monitored reaction progress and assessed efficiency via analytical techniques.

Main Results:

  • Achieved high efficiency in converting the peptide N-terminus to an azide.
  • Demonstrated successful transformation within a short reaction time of 30 minutes.
  • Confirmed the reagent's compatibility with both NovaPEG and polystyrene solid supports under distinct solvent conditions.

Conclusions:

  • Imidazole-1-sulfonyl azide hydrochloride is a versatile and effective reagent for N-terminal peptide azidation on solid phase.
  • The developed method offers a rapid and high-yielding route for preparing azide-functionalized peptides.
  • This reagent provides a valuable tool for streamlining peptide modification in solid-phase synthesis workflows.