| TOMEČEK, Josef, Andrea ČABLOVÁ, Aneta HROMÁDKOVÁ, Jan NOVOTNÝ, Radek MAREK, Ivo DURNÍK, Petr KULHÁNEK, Zdeňka PRUCKOVÁ, Michal ROUCHAL, Lenka DASTYCHOVÁ and Robert VÍCHA. Modes of Micromolar Host-Guest Binding of beta-Cyclodextrin Complexes Revealed by NMR Spectroscopy in Salt Water. The Journal of Organic Chemistry. American Chemical Society, 2021, vol. 86, No 6, p. 4483-4496. ISSN 0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.0c02917. |
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@article{1748200,
author = {Tomeček, Josef and Čablová, Andrea and Hromádková, Aneta and Novotný, Jan and Marek, Radek and Durník, Ivo and Kulhánek, Petr and Prucková, Zdeňka and Rouchal, Michal and Dastychová, Lenka and Vícha, Robert},
article_number = {6},
doi = {http://dx.doi.org/10.1021/acs.joc.0c02917},
keywords = {host-guest complex;cyclodextrin;NMR spectroscopy;molecular modeling;binding;salt water},
language = {eng},
issn = {0022-3263},
journal = {The Journal of Organic Chemistry},
title = {Modes of Micromolar Host-Guest Binding of beta-Cyclodextrin Complexes Revealed by NMR Spectroscopy in Salt Water},
url = {https://doi.org/10.1021/acs.joc.0c02917},
volume = {86},
year = {2021}
}
TY - JOUR
ID - 1748200
AU - Tomeček, Josef - Čablová, Andrea - Hromádková, Aneta - Novotný, Jan - Marek, Radek - Durník, Ivo - Kulhánek, Petr - Prucková, Zdeňka - Rouchal, Michal - Dastychová, Lenka - Vícha, Robert
PY - 2021
TI - Modes of Micromolar Host-Guest Binding of beta-Cyclodextrin Complexes Revealed by NMR Spectroscopy in Salt Water
JF - The Journal of Organic Chemistry
VL - 86
IS - 6
SP - 4483-4496
EP - 4483-4496
PB - American Chemical Society
SN - 00223263
KW - host-guest complex;cyclodextrin;NMR spectroscopy;molecular modeling;binding;salt water
UR - https://doi.org/10.1021/acs.joc.0c02917
N2 - 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.
ER -
TOMEČEK, Josef, Andrea ČABLOVÁ, Aneta HROMÁDKOVÁ, Jan NOVOTNÝ, Radek MAREK, Ivo DURNÍK, Petr KULHÁNEK, Zdeňka PRUCKOVÁ, Michal ROUCHAL, Lenka DASTYCHOVÁ and Robert VÍCHA. Modes of Micromolar Host-Guest Binding of beta-Cyclodextrin Complexes Revealed by NMR Spectroscopy in Salt Water. \textit{The Journal of Organic Chemistry}. American Chemical Society, 2021, vol.~86, No~6, p.~4483-4496. ISSN~0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.0c02917.
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