A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study. Issue 10 (1st July 2022)

• Record Type: Journal Article
• Authors: Mousavimanesh, Zohreh; Shahnani, Mostafa; Faraji‐Shovey, Amirmohammad; Bararjanian, Morteza; Sadr, Ahmad Shahir; Ghassempour, Alireza; Salehi, Peyman
• Is Part Of: Chirality. Volume 34:Issue 10(2022)
• Page Start: 1371
• Page End: 1382
• Publication Date: 2022-07-01
• Subjects: alkaloid‐based chiral selector -- docking simulation -- enantiomeric separation -- mandelic acid -- propranolol -- warfarin; Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.23488
• Languages: English
• ISSNs: 0899-0042

Abstract

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. Abstract : The current work provides authentic and applied research that discusses the application of functional organic material in the high‐performance liquid chromatography (HPLC) enantioseparation field. A new chiral stationary phase has been synthesized based on an affordable natural product (noscapine), demonstrating high efficiency and validated by molecular docking simulation. This study provides new insight into establishing natural compounds for application in separation science.