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Enantioselective binding of α-pinene and of some cyclohexanetriol derivatives by cyclodextrin hosts: A molecular modeling study

✍ Scribed by Black, Delbert R.; Parker, Craig G.; Zimmerman, S. Scott; Lee, Milton L.

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 730 KB
Volume: 17
Category: Article
ISSN: 0192-8651
DOI: 10.1002/(sici)1096-987x(199606)17:8<931::aid-jcc2>3.0.co;2-s

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✦ Synopsis

We have used molecular modeling to investigate the enantioselective separation of the monoterpene a-pinene on permethylated P-cyclodextrin and on a- cyclodextrin and the enantioselective separation of three cyclohexanetriol derivatives on permethylated P-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 rigidbody 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.

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## Abstract Capillary GC on permethyl α‐, β‐, and γ‐cyclodextrins has been applied to separate and quantify the enantiomers of some 2,3‐iso‐propylidene‐1,2,3‐cyclohexanetriol derivatives. Quantitative CGC data are compared to those obtained with chiral shift ^1^H NMR.