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. 2022 Oct;34(10):1371-1382.
doi: 10.1002/chir.23488. Epub 2022 Jul 1.

A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study

Zohreh Mousavimanesh  1 , Mostafa Shahnani  1 , Amirmohammad Faraji-Shovey  1 , Morteza Bararjanian  1 , Ahmad Shahir Sadr  2   3 , Alireza Ghassempour  1 , Peyman Salehi  1
Affiliations

A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study

Zohreh Mousavimanesh et al. Chirality. 2022 Oct.

Abstract

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.

Keywords: alkaloid-based chiral selector; docking simulation; enantiomeric separation; mandelic acid; propranolol; warfarin.

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References

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