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Molecular Recognition of Bridged Bis(β-cyclodextrin) Linked by the 4,4′-Diaminodiphenyl Sulfone Tether with Non-aromatic Oligopeptides

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Abstract

The molecular recognition behavior of 4,4′-diaminodiphenyl sulfone bis(β-cyclodextrin) 1 with representative non-aromatic oligopeptides (Leu-Gly, Gly-Leu, Glu-Glu, Met-Met, Gly-Gly, Gly-Gly-Gly and Gly-Pro) was investigated by circular dichroism, fluorescence, 1H and 2D NMR spectroscopy at 25 °C in phosphate buffer solutions (pH=7.20). From the circular dichroism and 2D NMR results, it is inferred that the phenyl moiety in the linker of bis(β-cyclodextrin) is partly self-included in the cyclodextrin cavity, and it is entirely expelled out of the cyclodextrin cavity upon complexation with oligopeptides. Owing to the cooperative sandwich binding mode, bis(β-cyclodextrin) not only affords the highest binding constant of 29200 L⋅mol−1 for the tripeptide Gly-Gly-Gly, but it also can recognize the size and hydrophobicity of oligopeptides. The bis(β-cyclodextrin) gives an exciting residue selectivity of up to 78.9 for the Gly-Gly-Gly/Glu-Glu pair, and a higher length selectivity of up to 28.1 for the Gly-Gly-Gly/Gly-Gly pair. These phenomena are discussed from the viewpoint of the size-fit concept and multipoint recognition between host and guest.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming, 650092, P.R. China

    Yan Zhao, Yong Cun Yang, Hao Shi, Yong Zhao & Shao Ming Chi

  2. School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P.R. China

    Hong You Zhu

  3. Experimental Center, Yunnan University, Kunming, 650091, P.R. China

    Rong Huang

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  1. Yan Zhao
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  2. Yong Cun Yang
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  4. Yong Zhao
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Correspondence to Yan Zhao.

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Zhao, Y., Yang, Y.C., Shi, H. et al. Molecular Recognition of Bridged Bis(β-cyclodextrin) Linked by the 4,4′-Diaminodiphenyl Sulfone Tether with Non-aromatic Oligopeptides. J Solution Chem 39, 987–998 (2010). https://doi.org/10.1007/s10953-010-9564-3

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