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

Jian Yang (1) , Bastien Chatelet (1) , Véronique Dufaud (2) , Damien Hérault (1) , Marion Jean (1) , Nicolas Vanthuyne (1) , Jean-Christophe Mulatier (2) , Delphine Pitrat (2) , Laure Guy (2) , Jean-Pierre Dutasta (2) , Alexandre Martinez (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 LC - Laboratoire de Chimie - UMR5182

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

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⟩