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Cyclodextrin homo- and hetero-dimers as enzyme models

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Journal of inclusion phenomena and molecular recognition in chemistry Aims and scope Submit manuscript

Abstract

Three kinds of dimers (one homo-dimer of β-CD and two kinds of hetero-dimers of α-CCD and β-CD) were synthesized as artificial hydrolases. The dimers were prepared by the condensation of 6-deoxy-6-(l-histidylamino)-cyclodextrin and 6 (carboxymethylthio)-6-deoxycyclodextrin with dicyclohexylcarbodiimide. The enzyme-like activities were studied by measuring the rates for the cleavage reaction of some kinds of nitrophenyl alkanoates. They showed large acceleration ability and substrate specificity for the acyl chain length of the substrate.As the acyl chain length of the substrate was longer, the transition state was more stabilized by the dimers. The only homo-dimer showed allosteric behavior with 1.8 Hill constant, whenp-nitrophenyl methoxyethoxyethoxyacetate was used for the substrate.

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Reference

  1. Ikeda, H., Kojin, R., Yoon, C-j., Ikeda, T., Toda, F., Artificial Hydrolase Using Modified Dimethyl-β-Cyclodextrin,J. Incl. Phenom.,7, 117 (1989)

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  2. Akiike, T., Nagano, Y., Yamamoto, Y., Nakamura, A., Ikeda, H., Ueno, A., Toda, F., Coupled Cyclodextrin Appending Imidazole as an Enzyme Model,Chem. Lett., 1089–1092 (1994).

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Authors and Affiliations

  1. Department of Bioengineering, Tokyo Institute of Technology, Nagatsuta-cho, Midori-ku, 226, Yokohama, Japan

    S. Nishikawa, J. Takaoka, T. Akiike, Y. Yamamoto & A. Ueno

  2. Polytechnic College, 2-32-1, Ogawanisi, 187, Kodaira, Japan

    F. Toda

Authors
  1. S. Nishikawa
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  2. J. Takaoka
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  3. T. Akiike
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  4. Y. Yamamoto
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  5. A. Ueno
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  6. F. Toda
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Nishikawa, S., Takaoka, J., Akiike, T. et al. Cyclodextrin homo- and hetero-dimers as enzyme models. J Incl Phenom Macrocycl Chem 25, 133–136 (1996). https://doi.org/10.1007/BF01041553

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  • DOI: https://doi.org/10.1007/BF01041553

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