A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study.
alkaloid-based chiral selector
docking simulation
enantiomeric separation
mandelic acid
propranolol
warfarin
Journal
Chirality
ISSN: 1520-636X
Titre abrégé: Chirality
Pays: United States
ID NLM: 8914261
Informations de publication
Date de publication:
10 2022
10 2022
Historique:
revised:
28
05
2022
received:
15
01
2022
accepted:
12
06
2022
pubmed:
3
7
2022
medline:
14
9
2022
entrez:
2
7
2022
Statut:
ppublish
Résumé
Noscapine is an isolated compound from the opium poppy, with distinctive chiral structure and chemistry, interacts with other compounds due to having multiple π-acceptors, hydrogen bond acceptors, and ionic sites. Therefore, it has promising applicability for the enantioselective separation of a wide range of polar, acidic, basic, and neutral compounds. A new noscapine derivative chiral stationary phase (ND-CSP) has been synthesized by consecutive N-demethylation, reduction, and N-propargylation of noscapine followed by attachment of a solid epoxy-functionalized silica bed through the 1,3-dipolar Huisgen cycloaddition. The noscapine derivative-based stationary phase provides a considerable surface coverage, which is greater than some commercial CSPs and can validate better enantioresolution performance. The major advantages inherent to this chiral selector are stability, reproducibility after more than 200 tests, and substantial loading capacity. The characterization by Fourier transform infrared (FTIR) spectroscopy and elemental analysis indicated successful functionalization of the silica surface. Chromatographic method conditions like flow rate and mobile phase composition for enantioseparation of various compounds such as warfarin, propranolol, mandelic acid, and a sulfanilamide derivative were optimized. Comparing the experimental results with docking data revealed a clear correlation between the calculated binding energy of ND-CSP and each enantiomer with the resolution of enantiomer peaks.
Substances chimiques
Silicon Dioxide
7631-86-9
Noscapine
8V32U4AOQU
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
1371-1382Informations de copyright
© 2022 Wiley Periodicals LLC.
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