Helical Chirality Induces a Substrate-Selectivity Switch in Carbohydrates Recognitions

Augustin Long (1) , Olivier Perraud (2) , Muriel Albalat (1) , Vincent Robert , Jean-Pierre Dutasta (2) , Alexandre Martinez (1)

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

A new chiral hemicryptophane cage combining an electron-rich cyclotriveratrylene (CTV) unit and polar amine functions has been synthesized. The resolution of the racemic mixture has been performed by chiral HPLC, and the assignment of the absolute configuration of the two enantiomers has been achieved using ECD spectroscopy. In contrast with other hemicryptophane receptors, the two enantiomeric hosts display both remarkable enantioselectivities in the recognition of carbohydrates and good binding constants. Moreover, by switching the chirality of the CTV unit from M to P, a strong preference shift from glucose to mannose derivatives is observed.

Domaines: Chimie organique

Augustin Long, Olivier Perraud, Muriel Albalat, Vincent Robert, Jean-Pierre Dutasta, et al.. Helical Chirality Induces a Substrate-Selectivity Switch in Carbohydrates Recognitions. Journal of Organic Chemistry, 2018, 83 (12), pp.6301 - 6306. ⟨10.1021/acs.joc.8b00276⟩. ⟨hal-01896109⟩