Enantioseparation and chiral recognition mechanism of new chiral derivatives of xanthones on macrocyclic antibiotic stationary phases

Journal of Chromatography. a
Carla FernandesMadalena M Pinto

Abstract

A chiral HPLC method using four macrocyclic antibiotic chiral stationary phases (CSPs) has been investigated for determination of the enantiomeric purity of fourteen new chiral derivatives of xanthones (CDXs). The separations were performed with the CSPs Chirobiotic T, Chirobiotic TAG, Chirobiotic V and Chirobiotic R under multimodal elution conditions (normal-phase, reversed-phase and polar ionic mode). The analyses were performed at room temperature in isocratic mode and UV and CD detection at a wavelength of 254 nm. The best enantioselectivity and resolution were achieved on Chirobiotic R and Chirobiotic T CSPs, under normal elution conditions, with R(S) ranging from 1.25 to 2.50 and from 0.78 to 2.06, respectively. The optimized chromatographic conditions allowed the determination of the enantiomeric ratio of eight CDXs, always higher than 99%. In order to better understand the chromatographic behavior at a molecular level, and the structural features associated with the chiral recognition mechanism, computational studies by molecular docking were carried out using VDock. These studies shed light on the mechanisms involved in the enantioseparation for this important class of chiral compounds.

References

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Citations

Jun 20, 2016·Journal of Chromatography. a·Gerhard K E Scriba
Jun 14, 2017·Chirality·Carla FernandesMadalena M M Pinto
Feb 24, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Andrea N L BatistaQuezia B Cass
Jan 13, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ye' Zaw PhyoCarla Fernandes
Jan 10, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·João RibeiroMadalena M M Pinto
Mar 3, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Joana TeixeiraCarla Fernandes
Jan 19, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Joana AraújoMaria Elizabeth Tiritan
Aug 17, 2020·Chirality·Mostafa ShahnaniAlireza Ghassempour
Mar 1, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Carla FernandesMadalena M M Pinto
Jan 21, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Madalena M M PintoSara Cravo

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