Enantio- and Substrate-Selective Recognition of Chiral Neurotransmitters with C 3 -Symmetric Switchable Receptors - Aix-Marseille Université Access content directly
Journal Articles Organic Letters Year : 2020

Enantio- and Substrate-Selective Recognition of Chiral Neurotransmitters with C 3 -Symmetric Switchable Receptors

Véronique Dufaud
Delphine Pitrat
Laure Guy
Jean-Pierre Dutasta

Abstract

We report on the synthesis of C 3-symmetric enantiopure cage molecules 1, which exhibit remarkable to exclusive enantioselective recognition properties toward chiral ammonium neurotransmitters. Strong changes in the substrate selectivity are also observed when different stereoisomers of 1 are used. Furthermore, protonation/deprotonation induces a reversible modification of the conformation of 1, which switches from an imploded to an inflated form, leading to ejection and reuptake of the guest initially encaged inside the cavity.
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Dates and versions

hal-02611848 , version 1 (23-03-2021)

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Cite

Jian Yang, Bastien Chatelet, Véronique Dufaud, Damien Hérault, Marion Jean, et al.. Enantio- and Substrate-Selective Recognition of Chiral Neurotransmitters with C 3 -Symmetric Switchable Receptors. Organic Letters, 2020, 22 (3), pp.891-895. ⟨10.1021/acs.orglett.9b04440⟩. ⟨hal-02611848⟩
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