Doubly chiral pseudopeptidic macrobicyclic molecular cages : Water-assisted dynamic covalent self-assembly and chiral self-sorting

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Author(s)

  • Ferran Esteve
  • Belén Altava
  • Eduardo García-Verdugo
  • Santiago V. Luis
  • Jean-Marie Lehn

Detail(s)

Original languageEnglish
Pages (from-to)2023-2042
Journal / PublicationChem
Volume8
Issue number7
Online published27 Jun 2022
Publication statusPublished - 14 Jul 2022
Externally publishedYes

Abstract

Taking advantage of the dynamic covalent chemistry approach, four different cages were synthesized by condensation of tripodal pseudopeptides with 4,4′-biphenyldicarboxyaldehyde. Whereas undesired products of polymeric nature were obtained in polar solvents, the [3+2] cryptand-type macrobicyclic architectures were obtained in excellent yields using chloroform as solvent, even at relatively high concentrations. The presence of two encapsulated water molecules may provide a positive template effect in the low polarity medium. The final macrobicycles display a combination of two types of chirality: D,L chirality due to the asymmetric α-C centers and P,M helical chirality. The homochiral helicity found for all the enantiomerically pure molecular cages indicates strong chirality induction by the asymmetric α-C. Besides, the self-sorting properties of the different chiral pseudopeptides have been studied, resulting in high-fidelity homo-self-sorting. DFT calculations point out that the self-sorting outcome may also be a direct result of the encapsulation of two water molecules within the cavity.

Research Area(s)

  • bioinspired, chirality, macrocyclization, molecular cages, pseudopeptides, SDG12: Responsible consumption and production, SDG9: Industry innovation and infrastructure, self-assembly, self-sorting, supramolecular, template, water assisted

Citation Format(s)

Doubly chiral pseudopeptidic macrobicyclic molecular cages: Water-assisted dynamic covalent self-assembly and chiral self-sorting. / Esteve, Ferran; Altava, Belén; García-Verdugo, Eduardo et al.
In: Chem, Vol. 8, No. 7, 14.07.2022, p. 2023-2042.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review