Molecular recognition by beta-cyclodextrin derivatives: FEP vs MM/PBSA study.
The complexation of p-tert-butylphenyl p-tert-butylbenzoate, N-(p-tert-butylphenyl)-p-tert-butylbenzamide and a bisadamantyl-phosphate derivative with a beta-cyclodextrin derivative formed by two cyclodextrin units linked by a disulfide bridge on one of the C6 atoms have been studied by computational methods (free energy perturbation (FEP) and Molecular Mechanics/Poisson Bolzmann Surface Area (MM/PBSA)). The calculated relative free energies of the amide and ester are in good agreement with experiment only for MM/PBSA and not for FEP. Only MM/PBSA was applied to the bisadamantyl-phosphate complex and its calculated association free energy was calculated to be similar to that of the ester, which is consistent with the experimental tendencies.
Beà
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I
Departament de Química, Universitat Autònoma de Barcelona, 08193, Bellaterra, Spain.
Cervelló
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E
Kollman
P A
PA
Jaime
C
C
D020650:Combinatorial Chemistry Techniques; D003198:Computer Simulation; D003505:Cyclodextrins / Q000737:chemistry* / Q000378:metabolism; D008956:Models, Chemical; D008958:Models, Molecular; D010636:Phenols / Q000737:chemistry; D047392:beta-Cyclodextrins
D003505:Cyclodextrins; D010636:Phenols; D047392:beta-Cyclodextrins; C031215:betadex; C006862:butylphen