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 a Vladimír ŠINDELÁŘ

Základní údaje

Originální název

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

Autoři

SOKOLOV, Jan (203 Česká republika, domácí), Adam ŠTEFEK (203 Česká republika, domácí) a Vladimír ŠINDELÁŘ (203 Česká republika, garant, domácí)

Vydání

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

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 2.863

Kód RIV

RIV/00216224:14310/20:00114331

Organizační jednotka

Přírodovědecká fakulta

DOI

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

UT WoS

000544057700025

Klíčová slova anglicky

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

Štítky

CF PROT, CF SAXS, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 17. 2. 2023 21:35, Mgr. Michaela Hylsová, Ph.D.

Anotace

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.

Návaznosti

EF17_043/0009632, projekt VaV

Název: CETOCOEN Excellence

GA18-21801S, projekt VaV

Název: Chirální bambusurily

Investor: Grantová agentura ČR, Chirální bambusurily

LM2018121, projekt VaV

Název: Výzkumná infrastruktura RECETOX (Akronym: RECETOX RI)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, RECETOX RI

LM2018127, projekt VaV

Název: Česká infrastruktura pro integrativní strukturní biologii (Akronym: CIISB)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Czech Infrastructure for Integrative Structural Biology

Citovat

SOKOLOV, Jan, Adam ŠTEFEK a Vladimír ŠINDELÁŘ. Functionalized Chiral Bambusurils: Synthesis and Host-Guest Interactions with Chiral Carboxylates. CHEMPLUSCHEM. WEINHEIM (GERMANY): Wiley - Verlag Chemie, 2020, roč. 85, č. 6, s. 1307-1314. ISSN 2192-6506. Dostupné z: 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 a Vladimír ŠINDELÁŘ. Functionalized Chiral Bambusurils: Synthesis and Host-Guest Interactions with Chiral Carboxylates. \textit{CHEMPLUSCHEM}. WEINHEIM (GERMANY): Wiley - Verlag Chemie, 2020, roč.~85, č.~6, s.~1307-1314. ISSN~2192-6506. Dostupné z: https://dx.doi.org/10.1002/cplu.202000261.

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