Design and synthesis of naphthalene-based chiral strong cation exchangers and their application for chiral separation of basic drugs.

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F21%3A00544592" target="_blank" >RIV/67985858:_____/21:00544592 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22310/21:43922641 RIV/60461373:22340/21:43922641

Výsledek na webu

<a href="http://hdl.handle.net/11104/0321887" target="_blank" >http://hdl.handle.net/11104/0321887</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/jssc.202100127" target="_blank" >10.1002/jssc.202100127</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Design and synthesis of naphthalene-based chiral strong cation exchangers and their application for chiral separation of basic drugs.

Popis výsledku v původním jazyce

In continuation of our efforts to synthesize a highly dedicated strong cation exchanger, we introduce four chiral stationary phases based on a laterally substituted naphthalene core featuring chiral 2-aminocyclohexansulfonic acid as the chiral cation-exchange site. The selectors were modified with two different terminal units, which enabled immobilization to the silica support by thiol–ene radical reaction or azide–yne click chemistry. The chromatographic parameters of these chiral stationary phases were determined using a set of chiral amines, mainly from the family of β-blocker pharmaceuticals. The chiral stationary phases immobilized by means of click chemistry were found to be superior to those possessing the sulfide linker to the silica support. The chromatographic results and visualization of density functional theory-calculated conformations of the selectors hint at a combination of a steric and electronic effect of the triazole ring in the course of chiral resolution of the target analytes.

Název v anglickém jazyce

Design and synthesis of naphthalene-based chiral strong cation exchangers and their application for chiral separation of basic drugs.

Popis výsledku anglicky

In continuation of our efforts to synthesize a highly dedicated strong cation exchanger, we introduce four chiral stationary phases based on a laterally substituted naphthalene core featuring chiral 2-aminocyclohexansulfonic acid as the chiral cation-exchange site. The selectors were modified with two different terminal units, which enabled immobilization to the silica support by thiol–ene radical reaction or azide–yne click chemistry. The chromatographic parameters of these chiral stationary phases were determined using a set of chiral amines, mainly from the family of β-blocker pharmaceuticals. The chiral stationary phases immobilized by means of click chemistry were found to be superior to those possessing the sulfide linker to the silica support. The chromatographic results and visualization of density functional theory-calculated conformations of the selectors hint at a combination of a steric and electronic effect of the triazole ring in the course of chiral resolution of the target analytes.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

20402 - Chemical process engineering

Projekt

<a href="/cs/project/GA20-06264S" target="_blank" >GA20-06264S: Separace enantiomerů chirálními membránami: Experiment a simulace</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2021

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Separation Science

ISSN

1615-9306

e-ISSN

1615-9314

Svazek periodika

44

Číslo periodika v rámci svazku

18

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

3348-3356

Kód UT WoS článku

000679656800001

EID výsledku v databázi Scopus

2-s2.0-85111530182