Enantio- and Substrate-Selective Recognition of Chiral Neurotransmitters with C 3 -Symmetric Switchable Receptors - Archive ouverte HAL
Article Dans Une Revue Organic Letters Année : 2020

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

Véronique Dufaud
Delphine Pitrat
Laure Guy
Jean-Pierre Dutasta

Résumé

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.

Domaines

Chimie
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Dates et versions

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

Identifiants

Citer

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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