Chiral, Sequence-Definable Foldamer-Derived Macrocycles

Toyah M.C. Warnock, Rajkumar Sundaram, Matthew P. Fitzpatrick, Christopher J. Serpell, Paul Dingwall, Peter C. Knipe

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Abstract

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.
Original languageEnglish
Pages (from-to)15632-15636
Number of pages5
JournalChemical Science
Volume12
Issue number47
Early online date10 Nov 2021
DOIs
Publication statusPublished - 21 Dec 2021

Keywords

  • General Chemistry

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