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Issue 10, 2009
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Enantioselective recognition of amino acids by chiral peptido-calix[4]arenes and thiacalix[4]arenes

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Abstract

In order to prepare new molecular hosts able to discriminate enantiomers of amino-acid derivatives, we have synthesized chiral thiacalix[4]arenes. Extensive studies using NMR and mass spectrometry techniques allow us to determine the major supramolecular interactions involved in the recognition process. Moreover, a titration study enables us to determine the binding constant between these new hosts and a series of amino-acid derivatives. Finally, we have also demonstrated that these calixarenes are able to discriminate enantiomers of amino-acid guests.

Graphical abstract: Enantioselective recognition of amino acids by chiral peptido-calix[4]arenes and thiacalix[4]arenes

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Article information


Submitted
08 Apr 2009
Accepted
07 Jul 2009
First published
20 Aug 2009

New J. Chem., 2009,33, 2128-2135
Article type
Paper

Enantioselective recognition of amino acids by chiral peptido-calix[4]arenes and thiacalix[4]arenes

J. Bois, I. Bonnamour, C. Duchamp, H. Parrot-Lopez, U. Darbost and C. Felix, New J. Chem., 2009, 33, 2128
DOI: 10.1039/B907190C

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