化学学报 ›› 2004, Vol. 62 ›› Issue (21): 2165-2170. 上一篇    下一篇

研究论文

新型手性酪氨酸修饰的锌卟啉对氨基酸酯的分子识别研究

王树军, 阮文娟, 罗代兵, 朱志昂   

  1. 南开大学化学系, 天津, 300071
  • 投稿日期:2004-03-04 修回日期:2004-05-14 发布日期:2014-02-17
  • 通讯作者: wjruan@nankai,edu.cn
  • 作者简介:阮文娟,E-mail:wjruan@nankai,edu.cn
  • 基金资助:
    国家自然科学基金(Nos.20171024,20271030)、天津市自然科学基金(No.023604011)及教育部留学回国人员科研基金资助项目.

Study on Molecular Recognition of Amino Acid Esters by Novel Tetraphenylporphinatozinc Complex Modified with Chiral Tyrosine

WANG Shu-Jun, RUAN Wen-Juan, LUO Dai-Bing, ZHU Zhi-Ang   

  1. Department of Chemistry, Nankai University, Tianjin 300071
  • Received:2004-03-04 Revised:2004-05-14 Published:2014-02-17

合成并表征了一种L型Boc酪氨酸修饰的自由卟啉(L-BocTyrTAPP)及其锌卟啉配合物Zn(L-BocTyr)TAPP.通过紫外-可见光谱滴定法,研究了手性锌卟啉配合物与四对对映异构的手性氨基酸酯客体在CHCl3中的分子识别行为.实验结果表明,在分子识别的过程中,缔合常数顺序均为D型略大于L型,且按K(PheOMe)>K(AIaOMe)>K(ValOMe)>K(LeuOMe)的顺序依次减小.同时,利用园二色光谱进一步阐述手性分子识别过程.此外,采用分子力学方法搜索了主客体体系的最低能量构象,从理论上对实验本质进行较深入的探讨.

关键词: 手性锌卟啉, 手性氨基酸酯客体, 手性分子识别, 园二色光谱, 分子力学

One kind of novel zinc prophyrin complex modified by L-BocTyrosine was synthesized and characterized. Molecular recognitions of four pairs of amino acid esters by the chiral zinc porphyrin have been investigated with UV Vis spectral method. The results show that association constants of the recognition process are all in the order of KD>KL, following the order K(PheOMe)>K(AIaOMe)>K(ValOMe)>K(LeuOMe). Circular dichroism spectra have been used to explain chiral molecular recognition. In addition, the conformations with minimal energy of host and host guest molecular systems were sought by molecular dynamics method. Experimental essence was more deeply discussed by theoretical calculation.

Key words: chiral zinc porphyrin, chiral amino acid ester, chiral molecular recognition, circular dichroism spectra, molecular mechanics