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A synthetic host-guest system achieves avidin-biotin affinity by overcoming enthalpy–entropy compensation

Open access
Rekharsky, Mikhail V., Mori, Tadashi, Yang, Cheng, Ko, Young Ho, Selvapalam, N., Kim, Hyunuk, Sobransingh, David, Kaifer, Angel E., Liu, Simin, Isaacs, Lyle, Chen, Wei, Moghaddam, Sarvin, Gilson, Michael K., Kim, Kimoon, Inoue, Yoshihisa·2007·Proceedings of the National Academy of Sciences

Abstract

The molecular host cucurbit[7]uril forms an extremely stable inclusion complex with the dicationic ferrocene derivative bis(trimethylammoniomethyl)ferrocene in aqueous solution. The equilibrium association constant for this host-guest pair is 3 × 10 15 M −1 ( K d = 3 × 10 −16 M), equivalent to that exhibited by the avidin–biotin pair. Although purely synthetic systems with larger association constants have been reported, the present one is unique because it does not rely on polyvalency. Instead, it achieves its extreme affinity by overcoming the compensatory enthalpy–entropy relationship usually observed in supramolecular complexes. Its disproportionately low entropic cost is traced to extensive host desolvation and to the rigidity of both the host and the guest.

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Metadata

Authors
Rekharsky, M. V., Mori, T., Yang, C., Ko, Y. H., Selvapalam, N., Kim, H., Sobransingh, D., Kaifer, A. E., Liu, S., Isaacs, L., Chen, W., Moghaddam, S., Gilson, M. K., Kim, K., & Inoue, Y.
Venue
Proceedings of the National Academy of Sciences
Published
2007-12-26
Volume
104
Issue
52
Pages
20737-20742
ISSN
  • 0027-8424 (ISSN-L)
  • 1091-6490
OpenAlex
W2009071379
Cited by
582
References
0
FWCI
14.66
Type
journal article
Language
en
Open access
green

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CoChat. (2026). Citation check: A synthetic host-guest system achieves avidin-biotin affinity by overcoming enthalpy–entropy compensation. https://app.cochat.ai/papers/10.1073/pnas.0706407105
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Rekharsky, M. V., Mori, T., Yang, C., Ko, Y. H., Selvapalam, N., Kim, H., Sobransingh, D., Kaifer, A. E., Liu, S., Isaacs, L., Chen, W., Moghaddam, S., Gilson, M. K., Kim, K., & Inoue, Y. (2007). A synthetic host-guest system achieves avidin-biotin affinity by overcoming enthalpy–entropy compensation. Proceedings of the National Academy of Sciences. https://doi.org/10.1073/pnas.0706407105

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