# Clicked H-Shaped Arylopeptoids

**Authors:** Zein El Abidine Chamas, Ayman Akhdar, Florence Charnay-Pouget, Sophie Faure, Arnaud Gautier

PMC · DOI: 10.3390/molecules30030724 · Molecules · 2025-02-05

## TL;DR

This paper describes a method to synthesize H-shaped and ladder-type compounds using a copper-catalyzed reaction, overcoming challenges in extending the structures.

## Contribution

A new method for synthesizing H-shaped arylpeptoids via CuAAC on-resin homodimerization is introduced.

## Key findings

- H-shaped N-alkylated aminomethyl oligobenzamides were successfully synthesized using CuAAC.
- A synthetic bottleneck was identified due to congestion during solid-support ligation.
- Inter-strand cross-linking with elongated oligomers resolved the elongation issue.

## Abstract

This study presents a tentative synthesis of supported H-shaped and ladder-type compounds. If the ladders were not accessible, probably due to distance misfits between the reactive centers, a facile method for the synthesis of H-shaped N-alkylated aminomethyl oligobenzamides, i.e., arylopeptoids by on-resin homodimerization via the Copper(I)-Catalyzed-Alkyne-Azide-Cycloaddition (CuAAC) reaction is reported. While successful, a synthetic bottleneck was identified for further oligomer elongation due to congestion when the ligation occurs on solid support. However, this issue was effectively addressed using an elongated oligomer to conduct inter-strand cross-linking. Further CuAAC functionalization could be performed after elongation with additional alkyne groups to enhance diversity.

## Linked entities

- **Chemicals:** Copper(I) (PubChem CID 104815), azide (PubChem CID 33558)

## Full text

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## Figures

9 figures with captions in the complete paper: https://tomesphere.com/paper/PMC11821099/full.md

## References

34 references — full list in the complete paper: https://tomesphere.com/paper/PMC11821099/full.md

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Source: https://tomesphere.com/paper/PMC11821099