BRADY, Kimberly G., Laura GILBERG, David SIGWALT, Joshua BISTANY-RIEBMAN, Steven MURKLI, Jared KLEMM, Petr KULHÁNEK, Vladimír ŠINDELÁŘ a 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, roč. 32, č. 9, s. 479-494. ISSN 1061-0278. Dostupné z: 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 a 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, roč.~32, č.~9, s.~479-494. ISSN~1061-0278. Dostupné z: https://dx.doi.org/10.1080/10610278.2020.1795173.
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