Conformationally mobile acyclic cucurbit[n]uril-type receptors derived from an S-shaped methylene bridged glycoluril pentamer

Logo poskytovatele

Varování

Publikace nespadá pod Pedagogickou fakultu, ale pod Přírodovědeckou fakultu. Oficiální stránka publikace je na webu muni.cz.
Autoři

BRADY Kimberly G. GILBERG Laura SIGWALT David BISTANY-RIEBMAN Joshua MURKLI Steven KLEMM Jared KULHÁNEK Petr ŠINDELÁŘ Vladimír ISAACS Lyle

Rok publikování 2020
Druh Článek v odborném periodiku
Časopis / Zdroj Supramolecular Chemistry
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
www https://www.tandfonline.com/doi/abs/10.1080/10610278.2020.1795173?journalCode=gsch20
Doi http://dx.doi.org/10.1080/10610278.2020.1795173
Klíčová slova Acyclic cucurbituril; molecular recognition; isothermal titration calorimetry; foldamer
Popis 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.
Související projekty:

Používáte starou verzi internetového prohlížeče. Doporučujeme aktualizovat Váš prohlížeč na nejnovější verzi.