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Enantioselective binding of α‐pinene and of some cyclohexanetriol derivatives by cyclodextrin hosts: A molecular modeling study
Author(s) -
Black Delbert R.,
Parker Craig G.,
Zimmerman S. Scott,
Lee Milton L.
Publication year - 1996
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/(sici)1096-987x(199606)17:8<931::aid-jcc2>3.0.co;2-s
Subject(s) - chemistry , enantioselective synthesis , enantiomer , cyclodextrin , docking (animal) , binding energy , computational chemistry , molecular model , stereochemistry , molecular recognition , molecule , organic chemistry , catalysis , medicine , physics , nursing , nuclear physics
We have used molecular modeling to investigate the enantioselective separation of the monoterpene α‐pinene on permethylated β‐cyclodextrin and on α‐cyclodextrin and the enantioselective separation of three cyclohexanetriol derivatives on permethylated β‐cyclodextrin. Using the Consistent Valence Force Field (CVFF) from Insight/Discover, we have carried out systematic rigid‐body docking grid searches on each of the optical antipodes of the organic guest molecules interacting with the cyclodextrins, followed by minimizations of the low‐energy docked structures. A statistical mechanical analysis of the minimized energies yields data that agree in four out of five cases with the experimental elution order of enantiomers. The computed energies of the rigid‐body docking before minimizations do not agree with the experimental results, suggesting that a conformational induced fit of the cyclodextrins upon binding of the organic guests may be involved in the mechanism of the chiral recognition. © 1996 by John Wiley & Sons, Inc.