Doubly chiral pseudopeptidic macrobicyclic molecular cages: Water-assisted dynamic covalent self-assembly and chiral self-sorting
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Doubly chiral pseudopeptidic macrobicyclic molecular cages: Water-assisted dynamic covalent self-assembly and chiral self-sortingAutoria
Data de publicació
2022-06-27Editor
ElsevierCita bibliogràfica
ESTEVE, Ferran, et al. Doubly chiral pseudopeptidic macrobicyclic molecular cages: Water-assisted dynamic covalent self-assembly and chiral self-sorting. Chem, 2022, vol. 8, no 7, p. 2023-2042.Tipus de document
info:eu-repo/semantics/articleVersió
info:eu-repo/semantics/submittedVersionParaules clau / Matèries
Resum
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 ... [+]
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. [-]
Publicat a
Chem, 2022, vol. 8, no 7Entitat finançadora
Advanced Research Grant SUPRADAPT | University of Strasbourg Institute for Advanced Study (USIAS) | Universitat Jaume I | Ministerio de Ciencia, Innovación y Universidades (Spain) | Agencia Estatal de Investigación (AEI), Spain | Ministerio de Educación, Cultura y Deporte, Spain
Codi del projecte o subvenció
290585 | UJI-B2019-40 | RTI2018-098233-B-C22 | FPU 2017/02060 | EST19/00278
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