Molecular recognition by β-cyclodextrin derivatives: Molecular dynamics, free-energy perturbation and molecular mechanics/Poisson-Boltzmann surface area goals and problems

Ivan Beà, Carlos Jaime, Peter Kollman

Research output: Contribution to journalArticleResearchpeer-review

26 Citations (Scopus)

Abstract

The complexation of p-tert-butylphenyl p-tert-butylbenzoate and N-(p-tert-butylphenyl)-p-tert-butylbenzamide with a β-cyclodextrin derivative formed by two cyclodextrin units linked by a disulfide bridge on one of the C6 atoms has been studied by computational methods. The better amide solubility and the better internal interactions of the ester complex explain the experimentally observed better association constant for the ester. The free-energy perturbation methodology and molecular mechanics/Poisson-Boltzmann surface area analysis have been used to explain the problem and to compare the results.
Original languageEnglish
Pages (from-to)286-292
JournalTheoretical Chemistry Accounts
Volume108
Issue number5
DOIs
Publication statusPublished - 1 Nov 2002

Keywords

  • Cyclodextrin inclusion complexes
  • Free-energy perturbation analysis
  • Molecular dynamics simulations
  • Molecular recognition

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