| BRADY, Kimberly G., Laura GILBERG, David SIGWALT, Joshua BISTANY-RIEBMAN, Steven MURKLI, Jared KLEMM, Petr KULHÁNEK, Vladimír ŠINDELÁŘ and Lyle ISAACS. Conformationally mobile acyclic cucurbit[n]uril-type receptors derived from an S-shaped methylene bridged glycoluril pentamer. Supramolecular Chemistry. Abingdon: Taylor & Francis Ltd., 2020, vol. 32, No 9, p. 479-494. ISSN 1061-0278. Available from: https://dx.doi.org/10.1080/10610278.2020.1795173. |
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@article{1707396,
author = {Brady, Kimberly G. and Gilberg, Laura and Sigwalt, David and BistanyandRiebman, Joshua and Murkli, Steven and Klemm, Jared and Kulhánek, Petr and Šindelář, Vladimír and Isaacs, Lyle},
article_location = {Abingdon},
article_number = {9},
doi = {http://dx.doi.org/10.1080/10610278.2020.1795173},
keywords = {Acyclic cucurbituril; molecular recognition; isothermal titration calorimetry; foldamer},
language = {eng},
issn = {1061-0278},
journal = {Supramolecular Chemistry},
title = {Conformationally mobile acyclic cucurbit[n]uril-type receptors derived from an S-shaped methylene bridged glycoluril pentamer},
url = {https://www.tandfonline.com/doi/abs/10.1080/10610278.2020.1795173?journalCode=gsch20},
volume = {32},
year = {2020}
}
TY - JOUR
ID - 1707396
AU - Brady, Kimberly G. - Gilberg, Laura - Sigwalt, David - Bistany-Riebman, Joshua - Murkli, Steven - Klemm, Jared - Kulhánek, Petr - Šindelář, Vladimír - Isaacs, Lyle
PY - 2020
TI - Conformationally mobile acyclic cucurbit[n]uril-type receptors derived from an S-shaped methylene bridged glycoluril pentamer
JF - Supramolecular Chemistry
VL - 32
IS - 9
SP - 479-494
EP - 479-494
PB - Taylor & Francis Ltd.
SN - 10610278
KW - Acyclic cucurbituril
KW - molecular recognition
KW - isothermal titration calorimetry
KW - foldamer
UR - https://www.tandfonline.com/doi/abs/10.1080/10610278.2020.1795173?journalCode=gsch20
L2 - https://www.tandfonline.com/doi/abs/10.1080/10610278.2020.1795173?journalCode=gsch20
N2 - We report the synthesis of the conformationally mobile S-shaped glycoluril pentamer building block3aand two new acyclic CB[n]-type receptorsP1andP2. P1(9 mM) andP2(11 mM) have moderate aqueous solubility but their host center dot guest complexes are poorly soluble. HostP1does not undergo intermolecular self-association whereasP2does (K-s = 189 +/- 27 M-1).(1) H NMR titrations show thatP1andP2are poor hosts towards hydrophobic (di)cations6-11(P1: K-a = 375-1400 M-1;P2: K-a = 1950-19,800 M-1) compared toTet1andTet2(Tet1: K-a = 3.09 x 10(6)to 4.69 x 10(8) M-1;Tet2: K-a = 4.59 x 10(8)to 1.30 x 10(10) M-1). Molecular modelling shows thatP1andP2exist as a mixture of three different conformers due to the two S-shaped methylene bridged glycoluril dimer subunits that each possess two different conformations. The lowest energy conformers ofP1andP2do not feature a well-defined central cavity. In the presence of guests,P2adapts its conformation to form 1:1P2 center dot guest complexes; the binding free energy pays the energetic price of conformer selection. This energetically unfavourable conformer selection results in significantly decreased K(a)values ofP1andP2compared toTet1andTet2.
ER -
BRADY, Kimberly G., Laura GILBERG, David SIGWALT, Joshua BISTANY-RIEBMAN, Steven MURKLI, Jared KLEMM, Petr KULHÁNEK, Vladimír ŠINDELÁŘ and Lyle ISAACS. Conformationally mobile acyclic cucurbit[n]uril-type receptors derived from an S-shaped methylene bridged glycoluril pentamer. \textit{Supramolecular Chemistry}. Abingdon: Taylor \&{} Francis Ltd., 2020, vol.~32, No~9, p.~479-494. ISSN~1061-0278. Available from: https://dx.doi.org/10.1080/10610278.2020.1795173.
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