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化学学报
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化学学报 ›› 2006, Vol. 64 ›› Issue (10): 989-996. 上一篇    下一篇

研究论文

瓜环对氨基酸的分子识别研究

丛航1,2，陶龙玲3，余亦华3，杨帆2，杜莹1,薛赛风*,1，陶朱1   

  1. (1贵州大学应用化学研究所 贵阳 550025)
    (2华东师范大学化学系 上海 200062)
    (3华东师范大学光谱学与波谱学教育部重点实验室 上海 200062)
  • 投稿日期:2005-10-11 修回日期:2006-01-10 发布日期:2006-05-25
  • 通讯作者: 薛赛风

Molecular Recognition of Aminoacid by Cucurbiturils

CONG Hang1,2, TAO Long-Ling3, YU Yi-Hua3, YANG Fan2, DU Ying1, XUE Sai-Feng*,1, TAO Zhu1   

  1. (1 Institute of Applied Chemistry, Guizhou University, Guiyang 550025)
    (2 Department of Chemistry, East China Normal University, Shanghai 200062)
    (3 Key Laboratory of Optical and Magnetic Resonance Spectroscopy of Ministry of Education of China,
    East China Normal University, Shanghai 200062)
  • Received:2005-10-11 Revised:2006-01-10 Published:2006-05-25
  • Contact: XUE Sai-Feng

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被引次数

4

使用1H NMR和UV-Vis光谱法研究了七、八元瓜环对九种天然氨基酸盐酸盐的分子识别作用. 结果表明, 瓜环对芳香侧基取代的L-酪氨酸、L-色氨酸、L-苯丙氨酸均能进行有效识别, 而侧链上不带芳香基团的氨基酸, 如L-组氨酸、L-谷氨酸、L-蛋氨酸、L-缬氨酸、L-白氨酸、L-丙氨酸, 与这些瓜环的作用相对较弱. 对于七元瓜环, 主客体间都以1∶1化学计量比形成包结物, 并得到它们相互作用的稳定常数; 八元瓜环与L-酪氨酸及L-色氨酸也以1∶1形成包结物, 而与L-苯丙氨酸以1∶2形成包结物. L-酪氨酸、L-色氨酸和L-苯丙氨酸荧光性质研究表明, 七、八元瓜环既可成为这些氨基酸荧光性质的增敏试剂, 也可成为它们荧光淬灭试剂, 这与氨基酸的结构有关.

关键词: 瓜环, 分子识别, 包结物, 氨基酸, 超分子

Molecular recognition properties of cucurbit(n)urils (n＝7, 8) [Q(7), Q(8)] toward aminoacid hydrochlorides were studied by 1H NMR and UV-Vis methods. The experimental results reveals that such hosts can exhibit a special recognition property toward an aromatic moiety of the aromatic aminoacids such as L-Tyr, L-Try and L-Phe, and a weak binding toward other aminoacids without the aromatic moiety, such as L-Ala. Q(7) with these guests always formed a host-guest complex with a 1∶1 ratio, and based on this model, the stability constants of the host-guest complexes were obtained. Q(8) with L-Tyr or L-Try formed a host-guest complex with a 1∶1 ratio. However, Q(8) with a 1∶2 ratio with L-Phe formed a host-guest complex. Studies on fluorescence properties of the aminoacids show that Q(7) or Q(8) could be an agent of fluorescence enhancement or fluorescence quenching, which was related to the structure of a certain aminoacid.

Key words: cucurbituril, molecular recognition, inclusion complex, aminoacid, supramolecular