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A synthetic host-guest system achieves avidin-biotin affinity by overcoming enthalpy–entropy compensation
Open accessAbstract
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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Citations
Cited by
Xia, D., Wang, P., Ji, X., Khashab, N. M., Sessler, J. L., & Huang, F. (2020) · Chemical Reviews · doi:10.1021/acs.chemrev.9b00839 · Cited by 734
Entropy-Enthalpy Compensation: Role and Ramifications in Biomolecular Ligand Recognition and Design
Chodera, J. D., & Mobley, D. L. (2013) · Annual Review of Biophysics · doi:10.1146/annurev-biophys-083012-130318 · Cited by 531
Moghaddam, S., Yang, C., Rekharsky, M., Ko, Y. H., Kim, K., Inoue, Y., & Gilson, M. K. (2011) · Journal of the American Chemical Society · doi:10.1021/ja109904u · Cited by 344
Self-citationSmith, A. J. T., Zhang, X., Leach, A. G., & Houk, K. N. (2009) · Journal of Medicinal Chemistry · doi:10.1021/jm800498e · Cited by 193
Cui, Q., Sulea, T., Schrag, J. D., Munger, C., Hung, M.-N., Naïm, M., Cygler, M., & Purisima, E. O. (2008) · Journal of Molecular Biology · doi:10.1016/j.jmb.2008.04.035 · Cited by 162
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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- 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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