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Updated: Mar 7, 2026

Synthesis and Mass Spectrometry Analysis of Oligo-peptoids
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1,2,3-Triazolium-Based Peptoid Oligomers.

Hafida Aliouat1,2, Cécile Caumes1, Olivier Roy1

  • 1Université Clermont Auvergne , CNRS, SIGMA Clermont, Institut de Chimie de Clermont-Ferrand, F-63000 Clermont-Ferrand, France.

The Journal of Organic Chemistry
|February 23, 2017
PubMed
Summary

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The 1,2,3-triazolium side chain strongly favors cis conformations in peptoid models, with minimal influence from sequence or solvent. This study details the synthesis of multitriazolium peptoids and analyzes counteranion effects on their structure.

Area of Science:

  • Organic Chemistry
  • Polymer Chemistry
  • Supramolecular Chemistry

Background:

  • Peptoids are peptide mimics with unique structural and functional properties.
  • 1,2,3-triazolium salts are emerging motifs in materials science and medicinal chemistry.
  • Controlling conformation in peptoid oligomers is crucial for designing functional materials.

Purpose of the Study:

  • To investigate the cis-directing effect of the 1,2,3-triazolium side chain in dimeric and oligomeric peptoid models.
  • To synthesize well-defined peptoid homooligomers featuring multiple pendant 1,2,3-triazolium units.
  • To evaluate the influence of sequence, solvent, and counteranion on the conformational preferences of these novel peptoid structures.

Main Methods:

  • Synthesis of peptoid dimers and homooligomers with varying sequences (αα, αβ, βα, ββ).

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  • Copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction for triazole formation.
  • Quaternization of triazoles to yield 1,2,3-triazolium salts.
  • Conformational analysis using NMR spectroscopy to determine cis/trans amide ratios.

    • Main Results:

    • The 1,2,3-triazolium side chain demonstrated a strong cis-directing effect, with cis amide conformations ranging from 83% to 94%.
    • Sequence and solvent exhibited minimal influence on the observed cis preference.
    • Well-defined peptoid homooligomers with four or eight pendant triazolium chains were successfully synthesized.
    • The nature of the counteranion (PF6-, BF4-, I-) influenced the conformational landscape of the multitriazolium peptoids.

    Conclusions:

    • The 1,2,3-triazolium moiety is a powerful conformational control element in peptoid backbones.
    • The synthesized multitriazolium peptoid platforms offer opportunities for developing new functional materials.
    • Further studies on counteranion engineering can fine-tune the properties of these peptoid systems.