Chiral zwitterionic stationary phases based on Cinchona alkaloids and dipeptides – design, synthesis and application in chiral separation

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F24%3A43929119" target="_blank" >RIV/60461373:22310/24:43929119 - isvavai.cz</a>

Výsledek na webu

<a href="https://www.sciencedirect.com/science/article/abs/pii/S0021967324000372" target="_blank" >https://www.sciencedirect.com/science/article/abs/pii/S0021967324000372</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.chroma.2024.464664" target="_blank" >10.1016/j.chroma.2024.464664</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Chiral zwitterionic stationary phases based on Cinchona alkaloids and dipeptides – design, synthesis and application in chiral separation

Popis výsledku v původním jazyce

Chiral resolution of polar organic compounds such as amino acids and peptides represents an important chromatographic task due to increasing significance of natural species, which play important signaling and regulatory roles in the living organisms. Despite the number of available chiral stationary phases, this task remains challenging, since not many of the commercially available systems are capable to resolve non-derivatized zwitterionic species. In this study, we present a target-oriented design of a new class of chiral selectors. Pursuing the goal to separate amino acids, and especially short peptides, we have combined Cinchona alkaloids – quinine and quinidine – with three different biogenic dipeptides. We have synthesized six different chiral stationary phases, with selector loading of ∼200 μmol g−1, and tested their chiral recognition capabilities for acidic, basic and zwitterionic analytes using various mobile phases. We have observed that all chiral stationary phases retain the chiral anion exchange capability known for commercially available Cinchona-based columns leading to baseline or partial resolution of six out of ten analytes. The performance in chiral resolution of basic analytes is not optimum due to the weak cation exchange character of the peptidic residue. However, we report on encouraging results in the chiral resolution of short peptides, for which, depending on their structure, we see the chiral resolution of up to three stereoisomers (from four possible) in a preliminary screening. © 2024

Název v anglickém jazyce

Chiral zwitterionic stationary phases based on Cinchona alkaloids and dipeptides – design, synthesis and application in chiral separation

Popis výsledku anglicky

Chiral resolution of polar organic compounds such as amino acids and peptides represents an important chromatographic task due to increasing significance of natural species, which play important signaling and regulatory roles in the living organisms. Despite the number of available chiral stationary phases, this task remains challenging, since not many of the commercially available systems are capable to resolve non-derivatized zwitterionic species. In this study, we present a target-oriented design of a new class of chiral selectors. Pursuing the goal to separate amino acids, and especially short peptides, we have combined Cinchona alkaloids – quinine and quinidine – with three different biogenic dipeptides. We have synthesized six different chiral stationary phases, with selector loading of ∼200 μmol g−1, and tested their chiral recognition capabilities for acidic, basic and zwitterionic analytes using various mobile phases. We have observed that all chiral stationary phases retain the chiral anion exchange capability known for commercially available Cinchona-based columns leading to baseline or partial resolution of six out of ten analytes. The performance in chiral resolution of basic analytes is not optimum due to the weak cation exchange character of the peptidic residue. However, we report on encouraging results in the chiral resolution of short peptides, for which, depending on their structure, we see the chiral resolution of up to three stereoisomers (from four possible) in a preliminary screening. © 2024

Druh

J_SC - Článek v periodiku v databázi SCOPUS

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GC21-31139J" target="_blank" >GC21-31139J: Nové chirální ionexy pro chromatografické enantioseparace</a><br>

Návaznosti

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

Rok uplatnění

2024

Kód důvěrnosti údajů

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

Název periodika

JOURNAL OF CHROMATOGRAPHY A

ISSN

0021-9673

e-ISSN

—

Svazek periodika

1717

Číslo periodika v rámci svazku

únor 2024

Stát vydavatele periodika

ZA - Jihoafrická republika

Počet stran výsledku

10

Strana od-do

464664

Kód UT WoS článku

—

EID výsledku v databázi Scopus

2-s2.0-85183044270