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化学学报
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化学学报 ›› 2002, Vol. 60 ›› Issue (2): 355-359. 上一篇    下一篇

研究论文

氨基甲酸酯型脱氧胆酸分子钳对氨基酸甲酯的手性识别 研究

薛翠花;牟其明;陈淑华   

  1. 四川大学化学学院.成都(610064)
  • 发布日期:2002-02-15

Enantioselective recognition of carbamate-type molecular tweezers derived from deoxycholic acid for amino acid methyl esters

Xue Cuihua;Mu Qiming;Chen Shuhua   

  1. Sichuan Univ, Coll Chem.Chengdu(610064)
  • Published:2002-02-15

PDF

484

被引次数

78

以脱氧胆酸为spacer，通过三光气桥连各种芳胺，合成了新的氨基甲酸酯型分子钳受体1～4，这些化合物的结构经IR，^1HNMR和元素分析所证实。利用差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1～4对所考察的氨基酸甲酯均具有识别能力，其对D-氨基酸甲酯的识别优于对L-氨基酸甲酯的识别。从主客体间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: 氨基甲酸酯, 脱氧胆酸, 分子钳, 对映体, 选择性, 氨基酸, 氨基酸甲酯, 分子识别, 手性识别

New chiral molecular tweezers 1～4 have been synthesized by using deoxycholic acid as a spacer to bridge the different aromatic amines. Their structures were confirmed by IR, ^1H NMR and elemental analysis. Enantioselective recognition properties of these molecular tweezers for amino acid methyl esters have been investigated by UV-vis spectra titration in CHCl3 at 25℃. The results indicate that molecular tweezers 1～4 not only recognize all amino acid methyl esters examined but also possess higher selectivity 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: CARBAMIC ACID ESTER, DEOXYCHOLIC ACID, ENANTIOMORPH, SELECTIVITY, AMINO ACID, OLECULAR RECOGNITION

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