Publication details

Modes of Micromolar Host-Guest Binding of beta-Cyclodextrin Complexes Revealed by NMR Spectroscopy in Salt Water

Authors

TOMEČEK Josef ČABLOVÁ Andrea HROMÁDKOVÁ Aneta NOVOTNÝ Jan MAREK Radek DURNÍK Ivo KULHÁNEK Petr PRUCKOVÁ Zdeňka ROUCHAL Michal DASTYCHOVÁ Lenka VÍCHA Robert

Year of publication 2021
Type Article in Periodical
Magazine / Source The Journal of Organic Chemistry
MU Faculty or unit

Central European Institute of Technology

Citation
Web https://doi.org/10.1021/acs.joc.0c02917
Doi http://dx.doi.org/10.1021/acs.joc.0c02917
Keywords host-guest complex;cyclodextrin;NMR spectroscopy;molecular modeling;binding;salt water
Description Multitopic supramolecular guests with finely tuned affinities toward widely explored cucurbit[n]urils (CBs) and cyclodextrins (CDs) have been recently designed and tested as functional components of advanced supramolecular systems. We employed various spacers between the adamantane cage and a cationic moiety as a tool for tuning the binding strength toward CB7 to prepare a set of model guests with K(CB7) and K(beta-CD) values of (0.6–5.0) × 1010 M–1 and (0.6–2.6) × 106 M–1, respectively. These accessible adamantylphenyl-based binding motifs open a way toward supramolecular components with an outstanding affinity toward beta-cyclodextrin. 1H NMR experiments performed in 30% CaCl2/D2O at 273 K along with molecular dynamics simulations allowed us to identify two arrangements of the guest@beta-CD complexes. The approach, joining experimental and theoretical methods, provided a better understanding of the structure of cyclodextrin complexes and related molecular recognition, which is highly important for the rational design of drug delivery systems, molecular sensors and switches.
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