Functionalized Chiral Bambusurils: Synthesis and Host-Guest
Interactions with Chiral Carboxylates

J 2020

Functionalized Chiral Bambusurils: Synthesis and Host-Guest Interactions with Chiral Carboxylates

SOKOLOV, Jan, Adam ŠTEFEK and Vladimír ŠINDELÁŘ

Basic information

Original name

Functionalized Chiral Bambusurils: Synthesis and Host-Guest Interactions with Chiral Carboxylates

Authors

SOKOLOV, Jan (203 Czech Republic, belonging to the institution), Adam ŠTEFEK (203 Czech Republic, belonging to the institution) and Vladimír ŠINDELÁŘ (203 Czech Republic, guarantor, belonging to the institution)

Edition

CHEMPLUSCHEM, WEINHEIM (GERMANY), Wiley - Verlag Chemie, 2020, 2192-6506

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10400 1.4 Chemical sciences

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 2.863

RIV identification code

RIV/00216224:14310/20:00114331

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1002/cplu.202000261

UT WoS

000544057700025

Keywords in English

anion receptors; enantioselective recognition; glycolurils; host-guest systems; macrocycles

Abstract

V originále

Bambusurils are a class of macrocyclic anion receptors that exhibit notable anion recognition properties, able to bind various inorganic anions as well the carboxylates or sulfonates. Recently, we reported enantioselective recognition of chiral carboxylates using non-functionalized chiral bambusuril derivatives. Herein, we report the synthesis and host-guest properties of two new representatives of chiral bambusuril macrocycles bearing ester functional groups, differing by the substituents attached to their portals. Their supramolecular properties in terms of carboxylate binding were studied by means of NMR in DMSO-d(6). The reported bambusurils bind selected chiral carboxylates with enantioselectivity factors up to 3.1. The results indicated that the selectivity towards different carboxylates is governed by the steric constraint of the substituents surrounding bambusuril portals. No clear trend in the binding affinities and their enantioselectivities was found.

Links

EF17_043/0009632, research and development project

Name: CETOCOEN Excellence

GA18-21801S, research and development project

Name: Chirální bambusurily

Investor: Czech Science Foundation

LM2018121, research and development project

Name: Výzkumná infrastruktura RECETOX (Acronym: RECETOX RI)

Investor: Ministry of Education, Youth and Sports of the CR, RECETOX RI

LM2018127, research and development project

Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

SOKOLOV, Jan, Adam ŠTEFEK and Vladimír ŠINDELÁŘ. Functionalized Chiral Bambusurils: Synthesis and Host-Guest Interactions with Chiral Carboxylates. CHEMPLUSCHEM. WEINHEIM (GERMANY): Wiley - Verlag Chemie, 2020, vol. 85, No 6, p. 1307-1314. ISSN 2192-6506. Available from: https://dx.doi.org/10.1002/cplu.202000261.

@article{1681018,
   author = {Sokolov, Jan and Štefek, Adam and Šindelář, Vladimír},
   article_location = {WEINHEIM (GERMANY)},
   article_number = {6},
   doi = {http://dx.doi.org/10.1002/cplu.202000261},
   keywords = {anion receptors; enantioselective recognition; glycolurils; host-guest systems; macrocycles},
   language = {eng},
   issn = {2192-6506},
   journal = {CHEMPLUSCHEM},
   title = {Functionalized Chiral Bambusurils: Synthesis and Host-Guest Interactions with Chiral Carboxylates},
   url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cplu.202000261},
   volume = {85},
   year = {2020}
}

TY  - JOUR
ID  - 1681018
AU  - Sokolov, Jan - Štefek, Adam - Šindelář, Vladimír
PY  - 2020
TI  - Functionalized Chiral Bambusurils: Synthesis and Host-Guest Interactions with Chiral Carboxylates
JF  - CHEMPLUSCHEM
VL  - 85
IS  - 6
SP  - 1307-1314
EP  - 1307-1314
PB  - Wiley - Verlag Chemie
SN  - 21926506
KW  - anion receptors
KW  - enantioselective recognition
KW  - glycolurils
KW  - host-guest systems
KW  - macrocycles
UR  - https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cplu.202000261
L2  - https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cplu.202000261
N2  - Bambusurils are a class of macrocyclic anion receptors that exhibit notable anion recognition properties, able to bind various inorganic anions as well the carboxylates or sulfonates. Recently, we reported enantioselective recognition of chiral carboxylates using non-functionalized chiral bambusuril derivatives. Herein, we report the synthesis and host-guest properties of two new representatives of chiral bambusuril macrocycles bearing ester functional groups, differing by the substituents attached to their portals. Their supramolecular properties in terms of carboxylate binding were studied by means of NMR in DMSO-d(6). The reported bambusurils bind selected chiral carboxylates with enantioselectivity factors up to 3.1. The results indicated that the selectivity towards different carboxylates is governed by the steric constraint of the substituents surrounding bambusuril portals. No clear trend in the binding affinities and their enantioselectivities was found.
ER  -

SOKOLOV, Jan, Adam ŠTEFEK and Vladimír ŠINDELÁŘ. Functionalized Chiral Bambusurils: Synthesis and Host-Guest Interactions with Chiral Carboxylates. \textit{CHEMPLUSCHEM}. WEINHEIM (GERMANY): Wiley - Verlag Chemie, 2020, vol.~85, No~6, p.~1307-1314. ISSN~2192-6506. Available from: https://dx.doi.org/10.1002/cplu.202000261.

Detailed Information on Publication Record