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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Templated Chromophore Assembly by Dynamic Covalent Bonds.

Lou Rocard¹, Andrey Berezin¹, Federica De Leo¹

¹Namur Research College (NARC) and Department of Chemistry University of Namur (UNamur), Rue de Bruxelles 61, Namur 5000 (Belgium).

Angewandte Chemie (International Ed. in English)

|December 5, 2015

Summary

Researchers developed a method to precisely arrange colored dyes on a peptide using dynamic covalent chemistry. This allows for controlled energy transfer between the dyes, demonstrating a new way to create functional molecular assemblies.

Keywords:

dynamic covalent chemistry energy transfer peptides self-assembly supramolecular chemistry

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Area of Science:

Supramolecular Chemistry
Organic Chemistry
Biophysical Chemistry

Background:

Dynamic covalent chemistry (DCC) offers reversible bond formation for self-assembly.
Orthogonal DCC reactions enable the independent formation of multiple bonds within a single system.
Precise spatial organization of functional molecules on peptide scaffolds is crucial for developing advanced materials.

Purpose of the Study:

To develop a facile and versatile protocol for the spatial organization of chromophores on an α-helix peptide scaffold.
To utilize three orthogonal dynamic covalent reactions for controlled dye assembly.
To investigate energy transfer processes and conformational stability of the assembled system.

Main Methods:

Simultaneous application of disulfide, boronate, and acyl hydrazone dynamic covalent reactions.
Assembly of blue, red, and yellow absorbing chromophores on a preprogrammed α-helix peptide.
Steady-state UV/Vis absorption and emission spectroscopy.
Molecular dynamics simulations.

Main Results:

Successful spatial organization of tailored chromophores in a desired ratio and spacing on the peptide.
Evidence of energy transfer from yellow and red donor dyes to a blue acceptor dye.
Experimental and simulation data confirmed the maintenance of the helical structure post-assembly.
Dyes were observed to be confined within defined conformational spaces on the peptide.

Conclusions:

The developed protocol provides a facile and versatile method for constructing precisely organized chromophore-peptide assemblies.
The system exhibits efficient energy transfer, suggesting potential applications in light-harvesting or sensing.
The conformational stability of the peptide scaffold is maintained, ensuring the integrity of the molecular architecture.