Design and Synthesis of Novel Molecular Tweezers Derived from Chenodeoxycholic Acid and Molecular Recognition Properties

Abstract

A novel type of chiral molecular tweezers has been designed and synthesized by using chenodeoxycholic acid as spacer and aromatic compounds as arm. Their structures were confirmed by ¹H NMR, IR, MS spectra and elemental analysis. Enantioselective recognition properties of these molecular tweezers for D/L-amino acid methyl esters have been investigated by UV-Vis spectra titration. The results indicate that molecular tweezers 3a～3e not only recognize al1 amino acid methyl esters examined but also possess higher selectivity for L-amino acid methyl esters than for D-amino acid methyl esters. The recognition ability and selectivity are discussed from the viewpoint of the size/shape-fit and geometrical complementary relationship between the molecular tweezers and amino acid methyl esters.

Key words: molecular tweezer, synthesis, molecular recognition, chenodeoxycholic acid

Cite this article

ZHAO Zhi-Gang^1,2,LIU Xing-Li²,YANG Zu-Xing,
TANG Xiao-Li²,CHEN Shu-Hua*^,1. Design and Synthesis of Novel Molecular Tweezers Derived from Chenodeoxycholic Acid and Molecular Recognition Properties[J]. Chin. J. Org. Chem., 2006, 26(04): 523-527.

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