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Chemistry. 2016 Jun 6;22(24):8038-42. doi: 10.1002/chem.201600664. Epub 2016 May 2.

Helical, Axial, and Central Chirality Combined in a Single Cage: Synthesis, Absolute Configuration, and Recognition Properties.

Author information

1
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, P. R. China.
2
Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, UCBL, 46 allée d'Italie, 69364, Lyon, France.
3
Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, UCBL, 46 allée d'Italie, 69364, Lyon, France. laure.guy@ens-lyon.fr.
4
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, P. R. China. ghgao@chem.ecnu.edu.cn.
5
Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, UCBL, 46 allée d'Italie, 69364, Lyon, France. alexandre.martinez@ens-lyon.fr.
6
Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397, Marseille, France. alexandre.martinez@ens-lyon.fr.

Abstract

The synthesis of eight enantiopure molecular cages (four diastereomeric pairs of enantiomers) comprising a helically chiral cyclotriveratrylene (CTV) unit, three axially chiral binaphthol linkages, and three centrally asymmetric carbon atoms of a trialkanolamine core, is described. These new cages constitute a novel family of hemicryptophanes, which combine three classes of chirality. Their absolute configuration was successfully assigned by a chemical correlation method to overcome the signals overlap in the ECD spectra of the binaphtol and CTV units. Stereoselective recognition of glucose and mannose derivatives was investigated with these new chiral cages. Excellent enantio- and diastereoselectivity were reached, since in some cases, both exclusive enantio- and diastereo-discrimination have been observed. In addition, compared with the most relevant hemicryptophanes, these new cages also exhibit improved binding affinities.

KEYWORDS:

carbohydrates; chirality; hemicryptophane; molecular cages; stereoselective recognition

PMID:
27037555
DOI:
10.1002/chem.201600664

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