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Study on the intermolecular complexation behavior between p-sulfonatocalix[4]arene with l-tyrosine

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Abstract

The formation of the complexation behavior of host molecules water-soluble p-sulfonatocalix[4]arene (p-SCX4) with l-tyrosine (l-Tyr) guest molecule has been studied by spectrophotometric including fluorescence and nuclear magnetic resonance (NMR) spectroscopy. Experimental conditions including concentration of p-SCX4 and medium acidity were investigated in detail. The results showed that p-SCX4 forms 1:1 complexes with l-Tyr in water. Their stability constant determined by spectrofluorometric titration is 15761 L mol. Moreover, to obtain information about the binding mechanism of the interaction, 1H NMR studies were carried out showing that the water-soluble p-SCX4 was found to be able to complex the aromatic l-Tyr, and the part of benzene ring of amino acid penetrated into the hydrophobic cavity of calix[4]arene and charged aliphatic chain of l-Tyr stick out of the cavity. In addition, the thermodynamic parameters for the complexation of p-SCX4 with l-Tyr were determined through Van’t Hoff analysis. The obtained data further confirmed the binding mode of p-SCX4 with l-Tyr. The related mechanism is proposed to explain the complexation processes.

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Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 90813018) and Youth Foundation of Shanxi Province (Nos. 2008021011, 2007021007 and 2010021014).

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Authors and Affiliations

  1. Center of Environmental Science and Engineering Research, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006, China

    Guomei Zhang, Yinghui Li, Xuan Zhao, jianbin Chao, Caihong Zhang, Guangming Wen, Shaomin Shuang & Chuan Dong

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  1. Guomei Zhang
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  2. Yinghui Li
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Correspondence to Guomei Zhang or Chuan Dong.

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Zhang, G., Li, Y., Zhao, X. et al. Study on the intermolecular complexation behavior between p-sulfonatocalix[4]arene with l-tyrosine. J Incl Phenom Macrocycl Chem 72, 473–479 (2012). https://doi.org/10.1007/s10847-011-9963-0

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