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Citation: ZHAO Hui, XUE Cui-Hua, MU Qi Ming, LI Ling, CHEN Shu-Hua. Enantioselective Recognition of Amino Acid Methyl Ester by Chiral Molecular Tweezers Derived from Deoxycholic Acid[J]. Chinese Journal of Applied Chemistry, ;2001, 18(8): 614-617. shu

Enantioselective Recognition of Amino Acid Methyl Ester by Chiral Molecular Tweezers Derived from Deoxycholic Acid

1.
The Faculty of Chemistry, Sichuan University, Chengdu 610064

Received Date: 14 November 2000
Available Online: 27 February 2001
Fund Project: 国家自然科学基金资助项目(20072026) (20072026)

The molecular recognition properties of four chiral molecular tweezers derived from deoxycholic acid for amino acid methyl esters have been investigated by UV Vis spectroscopic titration. The association constants (K_a) and Gibbs free energy changes (-ΔG⁰) have been calculated. The results show that all the molecular tweezers 1~4 can form 1:1 inclusion complexes with methyl esters of D/L-phenylalanine and leucine. The recognition ability of these receptors comes mainly from hydrogen bonding and van der Waals interaction. The size/shape-fitting and geometrical complement between receptor and substrate play an important role in the inclusion complexation of amino acid methyl esters with molecular tweezers 1~4.
- chiral recognition,
- molecular tweezer,
- deoxycholic acid,
- amino acid,
- UV spectroscopy
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