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

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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https://hal.archives-ouvertes.fr/hal-02611848
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Submitted on : Tuesday, March 23, 2021 - 6:01:42 PM
Last modification on : Sunday, June 26, 2022 - 3:06:35 AM

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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, American Chemical Society, 2020, 22 (3), pp.891-895. ⟨10.1021/acs.orglett.9b04440⟩. ⟨hal-02611848⟩

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