Effect of different immobilization strategies on chiral recognition properties of Cinchona-based anion exchangers

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F18%3A43916386" target="_blank" >RIV/60461373:22310/18:43916386 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388963:_____/18:00489905

Výsledek na webu

<a href="http://dx.doi.org/10.1002/jssc.201701213" target="_blank" >http://dx.doi.org/10.1002/jssc.201701213</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/jssc.201701213" target="_blank" >10.1002/jssc.201701213</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Effect of different immobilization strategies on chiral recognition properties of Cinchona-based anion exchangers

Popis výsledku v původním jazyce

In the enantiomeric separation of highly polar compounds, a traditionally challenging task for high-performance liquid chromatography, ion-exchange chiral stationary phases have found the main field of application. In this contribution, we present a series of novel anion-exchange-type chiral stationary phases for enantiomer separation of protected amino phosphonates and N-protected amino acids. Two of the prepared selectors possessed a double and triple bond within a single molecule. Thus, they were immobilized onto silica support employing either a thiol-ene (radical) or an azide-yne (copper(I)-catalyzed) click reaction. We evaluated the selectivity and the effect of immobilization proceeding either by the double bond of the Cinchona alkaloid or a triple bond of the carbamoyl moiety on the chromatographic performance of the chiral stationary phases using analytes with protecting groups of different size, flexibility, and pi-acidity. The previously observed preference toward protecting groups possessing pi-acidic units, which is a typical feature of Cinchona-based chiral stationary phases, was preserved. In addition, increasing the bulkiness of the selectors&apos; carbamoyl units leads to significantly reduced retention times, while very high selectivity toward the tested analytes is retained.

Název v anglickém jazyce

Effect of different immobilization strategies on chiral recognition properties of Cinchona-based anion exchangers

Popis výsledku anglicky

In the enantiomeric separation of highly polar compounds, a traditionally challenging task for high-performance liquid chromatography, ion-exchange chiral stationary phases have found the main field of application. In this contribution, we present a series of novel anion-exchange-type chiral stationary phases for enantiomer separation of protected amino phosphonates and N-protected amino acids. Two of the prepared selectors possessed a double and triple bond within a single molecule. Thus, they were immobilized onto silica support employing either a thiol-ene (radical) or an azide-yne (copper(I)-catalyzed) click reaction. We evaluated the selectivity and the effect of immobilization proceeding either by the double bond of the Cinchona alkaloid or a triple bond of the carbamoyl moiety on the chromatographic performance of the chiral stationary phases using analytes with protecting groups of different size, flexibility, and pi-acidity. The previously observed preference toward protecting groups possessing pi-acidic units, which is a typical feature of Cinchona-based chiral stationary phases, was preserved. In addition, increasing the bulkiness of the selectors&apos; carbamoyl units leads to significantly reduced retention times, while very high selectivity toward the tested analytes is retained.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10406 - Analytical chemistry

Projekt

<a href="/cs/project/GJ16-17689Y" target="_blank" >GJ16-17689Y: Nové chirální stacionární fáze ionexové povahy pro enantiomerní separace</a><br>

Návaznosti

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

Rok uplatnění

2018

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

—

Svazek periodika

41

Číslo periodika v rámci svazku

6

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

10

Strana od-do

1355-1364

Kód UT WoS článku

000428797000020

EID výsledku v databázi Scopus

—