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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (04): 523-527. 上一篇    下一篇

研究论文

新型鹅去氧胆酸分子钳的设计合成和分子识别性质研究

赵志刚1,2，刘兴利2，杨祖幸1，唐晓丽2，陈淑华*,1   

  1. (1四川大学化学学院 成都 610064)
    (2西南民族大学化学与环境保护工程学院 成都 610041)
  • 收稿日期:2005-11-17 修回日期:2006-02-26 发布日期:2006-03-31
  • 通讯作者: 陈淑华

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

ZHAO Zhi-Gang1,2,LIU Xing-Li2,YANG Zu-Xing1,
TANG Xiao-Li2,CHEN Shu-Hua*,1   

  1. (1 Faculty of Chemistry, Sichuan University, Chengdu 610064)
    (2 College of Chemistry and Environmental Protection Engineering, Southwest University for Nationali-ties, Chengdu 610041)
  • Received:2005-11-17 Revised:2006-02-26 Published:2006-03-31
  • Contact: CHEN Shu-Hua*<

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1121

被引次数

21

以鹅去氧胆酸为隔离基, 芳香族化合物为手臂设计合成了一类新型的分子钳, 其结构经1H NMR, IR, MS及元素分析确证. 利用紫外光谱滴定法考察了其与D/L氨基酸甲酯的对映选择性识别性能. 结果表明, 分子钳3a～3e对所考察的氨基酸甲酯均具有识别能力, 其对L-氨基酸甲酯的识别优于对D-氨基酸甲酯的识别. 从主客体的大小形状匹配及几何互补关系等方面对这些受体的识别能力及对映选择性进行了讨论.

关键词: 鹅去氧胆酸, 分子钳, 合成, 分子识别

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