Modes of Micromolar Host-Guest Binding of beta-Cyclodextrin Complexes Revealed by NMR Spectroscopy in Salt Water
| Authors | |
|---|---|
| Year of publication | 2021 |
| Type | Article in Periodical |
| Magazine / Source | The Journal of Organic Chemistry |
| MU Faculty or unit | |
| 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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