Issue 47, 2021

Chiral, sequence-definable foldamer-derived macrocycles


Nature's oligomeric macromolecules have been a long-standing source of inspiration for chemists producing foldamers. Natural systems are frequently conformationally stabilised by macrocyclisation, yet this approach has been rarely adopted in the field of foldamer chemistry. Here we present a new class of chiral cyclic trimers and tetramers formed by macrocyclisation of open-chain foldamer precursors. Symmetrical products are obtained via a [2 + 2] self-assembly approach, while full sequence control is demonstrated through linear synthesis and cyclisation of an unsymmetrical trimer. Structural characterisation is achieved through a combined X-ray and DFT approach, which indicates the tetramers adopt a near-planar conformation, while the trimers adopt a shallow bowl-like shape. Finally, a proof-of-concept experiment is conducted to demonstrate the macrocycles' capacity for cation binding.

Graphical abstract: Chiral, sequence-definable foldamer-derived macrocycles

Supplementary files

Article information

Article type
Edge Article
10 Sep 2021
03 Nov 2021
First published
10 Nov 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 15632-15636

Chiral, sequence-definable foldamer-derived macrocycles

T. M. C. Warnock, S. Rajkumar, M. P. Fitzpatrick, C. J. Serpell, P. Dingwall and P. C. Knipe, Chem. Sci., 2021, 12, 15632 DOI: 10.1039/D1SC05021D

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