Chinese Journal of Organic Chemistry >
Study of the Interaction between Two Kinds of Cucurbit [7]urils and 3-(2-Naphthyl)-alanine
Received date: 2018-01-13
Revised date: 2018-02-08
Online published: 2018-02-11
Supported by
Project supported by the National Natural Science Foundation of China (No. 21561007), the Science and Technology Fund of Guizhou Province (No. 2016-1030), the Innovation Program for High-Level Talents of Guizhou Province (No. 2016-5657) and the Major Program for Creative Research Groups of Guizhou Provincial Education Department (No. 2017-028).
The interaction of a pair of amino acid enantiomers, L-3-(2-naphthyl)-alanine (L-NA) and D-3-(2-naphthyl)-alanine (D-NA), with cucurbit[7]uril (Q[7]) and inverted cucurbit[7]uril (iQ[7]) was investigated, respectively, by using NMR spectroscopy, electronic absorption spectroscopy, fluorescence spectroscopies, isothermal titration calorimetry (ITC) experiments and MALDI-TOF mass spectrometry. Furthermore, the similarities and differences of the self-assembly patterns between the two kinds of cucurbituril with different cavity sizes and this pair of amino acid enantiomers were also researched. The results obtained from the experiment revealed that the naphthyl groups of amino acids were all entrapped in the cavity of the Q[n]s, whereas the other section of amino acids remained outside the portal and thus resulted in a more stable supramolecular self-assembly at a 1:1 ratio. Meanwhile, we found that the two different kinds of cucurbit[7]urils showed a slightly different selectivity for the L/D-NA chiral enantiomer.
Key words： inverted cucurbit[7]uril; cucurbit[7]uril; enantiomer; amino acid; self-assembly
Bai Dong , Zhou Yang , Lu Jihong , Liu Qingyun , Chen Qing , Tao Zhu , Xiao Xin . Study of the Interaction between Two Kinds of Cucurbit [7]urils and 3-(2-Naphthyl)-alanine[J]. Chinese Journal of Organic Chemistry, 2018 , 38(6) : 1477 -1483 . DOI: 10.6023/cjoc201801020
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