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.

Basic information

Original name

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

Authors

BRADY, Kimberly G. (840 United States of America), Laura GILBERG (276 Germany, belonging to the institution), David SIGWALT (840 United States of America), Joshua BISTANY-RIEBMAN (840 United States of America), Steven MURKLI (840 United States of America), Jared KLEMM (840 United States of America), Petr KULHÁNEK (203 Czech Republic, belonging to the institution), Vladimír ŠINDELÁŘ (203 Czech Republic, guarantor, belonging to the institution) and Lyle ISAACS

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10400 1.4 Chemical sciences

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

Impact factor

Impact factor: 1.688

RIV identification code

RIV/00216224:14310/20:00117313

Organization unit

Faculty of Science

DOI

UT WoS

000559579000001

Keywords in English

Acyclic cucurbituril; molecular recognition; isothermal titration calorimetry; foldamer

Tags

Tags

International impact, Reviewed
Změněno: 17/2/2023 21:47, Mgr. Michaela Hylsová, Ph.D.

Abstract

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.

Links

EF16_013/0001761, research and development project
Name: RECETOX RI
LM2015051, research and development project
Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX RI)
Investor: Ministry of Education, Youth and Sports of the CR
LM2015085, research and development project
Name: CERIT Scientific Cloud (Acronym: CERIT-SC)
Investor: Ministry of Education, Youth and Sports of the CR, CERIT Scientific Cloud
LQ1601, research and development project
Name: CEITEC 2020 (Acronym: CEITEC2020)
Investor: Ministry of Education, Youth and Sports of the CR
90042, large research infrastructures
Name: CESNET II