TY - JOUR
T1 - Molecular recognition by β-cyclodextrin derivatives: Molecular dynamics, free-energy perturbation and molecular mechanics/Poisson-Boltzmann surface area goals and problems
AU - Beà, Ivan
AU - Jaime, Carlos
AU - Kollman, Peter
PY - 2002/11/1
Y1 - 2002/11/1
N2 - 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.
AB - 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.
KW - Cyclodextrin inclusion complexes
KW - Free-energy perturbation analysis
KW - Molecular dynamics simulations
KW - Molecular recognition
U2 - 10.1007/s00214-002-0384-4
DO - 10.1007/s00214-002-0384-4
M3 - Article
SN - 1432-881X
VL - 108
SP - 286
EP - 292
JO - Theoretical Chemistry Accounts
JF - Theoretical Chemistry Accounts
IS - 5
ER -