高等学校化学学报

高等学校化学学报

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新型手性咪唑鎓环番的合成及对氨基酸的对映选择性识别

郭生金1,2, 罗奎1, 王文海1, 张仕勇1, 蒋和雁1, 兰静波1, 谢如刚1   

    1. 四川大学化学系, 成都 610064;
    2. 晋中学院生物科学与技术系, 榆次 030600
  • 收稿日期:2005-08-18 修回日期:1900-01-01 出版日期:2006-09-10 发布日期:2006-09-10
  • 通讯作者: 谢如刚

Design and Synthesis of Novel Chiral Imidazolium Cyclophanes and Their Enantioselective Recognition for α-Amino Acids and Their Derivatives

GUO Sheng-Jin1,2, LUO Kui1, WANG Wen-Hai1, ZHANG Shi-Yong1, JIANG He-Yan1,
LAN Jing-Bo1, XIE Ru-Gang1*   

    1. Department of Chemistry, Sichuan University, Chengdu 610064, China;
    2. Department of Bioscience and Technology, Jinzhong College, Yuci 030600, China
  • Received:2005-08-18 Revised:1900-01-01 Online:2006-09-10 Published:2006-09-10
  • Contact: XIE Ru-Gang

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被引次数

29

摘要： 以L-氨基酸为手性源, 合成了一系列新型手性咪唑鎓环番, 并进行了结构表征. 在碱性条件下, L氨基酸和乙二醛、甲醛缩合生成了(S)-2-(1-咪唑)羧酸钠, 转化为甲酯后与乙二胺进行胺解反应制得开链手性咪唑二酰胺, 然后与二溴化合物在高稀淡技术和无水条件下进行季铵化关环反应, 再进行阴离子交换制得目标分子(4~6). 以手性咪唑鎓环番为主体分子, 研究了对氨基酸及其衍生物的对映选择性识别作用.

关键词: 氨基酸, 手性咪唑鎓环番, 合成, 对映选择性识别

Abstract: A series of novel chiral imidazolium cyclophanes were synthesized from natural amino acids. (S)-2-(1-Imidazolyl)alkanoates(2) were prepared by cyclization and esterification. In the presence of DMAP and Et3N. Alkanoates(2) reacted with ethylenediamine to yield compounds 3 with satisfactory yields. Compounds 3 reacted with 2,6-bis(bromomethyl)-4-chlorphenol, 1,3-bis(bromomethyl)benzene or 2,6-bis(bromomethyl)pyridine to afford dibromide salts under high dilution and anhydrous condition. Finally, the hexafluorophosphates (4—6) were obtained by treating the corresponding dibromide salts with a saturated aqueous solution of NH4PF6. The structures of the target compounds were confirmed by IR, 1H NMR, MS, HRMS, and elemental analysis. These compounds featured large cavities and multipoint binding sites. UV spectroscopic titration experiments showed these chiral imidazolium cyclophanes exhibited good enantioselective recognition toward L- and D-amino acids and their derivatives.

Key words: Amino acid, Chiral imidazolium cyclophane, S ynthesis, Enantioselective recognition

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