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Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library

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Published on: June 20, 2014

Peptide mimics by linear arylamides: a structural and functional diversity test.

Zhan-Ting Li¹, Jun-Li Hou, Chuang Li

¹State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China. ztli@mail.sioc.ac.cn

Accounts of Chemical Research

|March 26, 2008

Summary

This study introduces arylamide foldamers, rigid peptide mimics stabilized by hydrogen bonds, showcasing their potential as versatile frameworks for molecular recognition and self-assembly applications.

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Area of Science:

Supramolecular Chemistry
Organic Chemistry
Materials Science

Background:

Hydrogen-bonded oligoamide foldamers are peptide mimics with established applications in chemical biology and drug design.
Previous work focused on aliphatic amino acid-based foldamers.
Arylamide-based foldamers offer a new class of rigid structures for advanced applications.

Purpose of the Study:

To create and investigate arylamide-based foldamers stabilized by hydrogen bonding.
To determine if these mimic structures possess sufficient rigidity for novel functions.
To explore their potential in molecular recognition, self-assembly, and materials science.

Main Methods:

Construction of three classes of arylamide oligomers (folded/helical, zigzag, straight) using amide and hydrazide units.
Stabilization of compact conformations via O...H-N and F...H-N hydrogen bonding.
Characterization using NMR, UV-vis, fluorescence, circular dichroism, and X-ray diffraction.

Main Results:

Demonstrated arylamide foldamers' ability to act as acyclic molecular receptors for cations and saccharides.
Showcased their utility in accelerating anisole hydrolysis and facilitating macrocyclization.
Reported on homoduplex assembly, molecular tweezers, nano-network formation with fullerenes, and dynamic [2]catenane synthesis.

Conclusions:

Hydrogen-bonding-driven arylamide oligomers represent a unique class of structurally rigid mimic structures.
These foldamers can function as synthetic receptors and serve as building blocks for complex architectures.
The developed frameworks offer facile functionalization, opening new avenues in molecular recognition and self-assembly.