Chiral zwitterionic stationary phases based on Cinchona alkaloids and dipeptides – design, synthesis and application in chiral separation
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Chiral zwitterionic stationary phases based on Cinchona alkaloids and dipeptides – design, synthesis and application in chiral separation
Original language description
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
Czech name
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Czech description
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Classification
Type
J<sub>SC</sub> - Article in a specialist periodical, which is included in the SCOPUS database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GC21-31139J" target="_blank" >GC21-31139J: Novel chiral ion-exchangers for chromatographic enantioseparations</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
JOURNAL OF CHROMATOGRAPHY A
ISSN
0021-9673
e-ISSN
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Volume of the periodical
1717
Issue of the periodical within the volume
únor 2024
Country of publishing house
ZA - SOUTH AFRICA
Number of pages
10
Pages from-to
464664
UT code for WoS article
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EID of the result in the Scopus database
2-s2.0-85183044270