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

J 2020

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

BRADY, Kimberly G.; Laura GILBERG; David SIGWALT; Joshua BISTANY-RIEBMAN; Steven MURKLI et al.

Základní údaje

Originální název

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

Autoři

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

Vydání

Supramolecular Chemistry, Abingdon, Taylor & Francis Ltd. 2020, 1061-0278

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 1.688

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/20:00117313

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

Acyclic cucurbituril; molecular recognition; isothermal titration calorimetry; foldamer

Štítky

14313010, 143180, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 3. 6. 2025 21:23, Mgr. Michaela Hylsová, Ph.D.

Anotace

V originále

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.

Návaznosti

EF16_013/0001761, projekt VaV

Název: RECETOX RI

LM2015085, projekt VaV

Název: CERIT Scientific Cloud (Akronym: CERIT-SC)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, CERIT Scientific Cloud

LQ1601, projekt VaV

Název: CEITEC 2020 (Akronym: CEITEC2020)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, CEITEC 2020

90042, velká výzkumná infrastruktura

Název: CESNET II

90051, velká výzkumná infrastruktura

Název: RECETOX II

Citovat

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://doi.org/10.1080/10610278.2020.1795173.

@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 = {https://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://doi.org/10.1080/10610278.2020.1795173.

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