期刊
JOURNAL OF CHROMATOGRAPHY A
卷 1241, 期 -, 页码 60-68出版社
ELSEVIER SCIENCE BV
DOI: 10.1016/j.chroma.2012.04.011
关键词
Macrocyclic antibiotic; Chiral stationary phases; Chiral derivatives of xanthones; Enantioselectivity; Enantiomeric purity; Chiral recognition
资金
- FCT - Fundacao para a Ciencia e a Tecnologia [CEQUIMED-PEst-OE/SAU/UI4040/2011, PEst-OE/QUI/UI0674/2011, FCT-Grices/Capes 00770 29/05/08]
- FEDER [FCOMP-01-0124-FEDER-011057]
- Fundação para a Ciência e a Tecnologia [PEst-OE/QUI/UI0674/2011] Funding Source: FCT
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. (c) 2012 Elsevier B.V. All rights reserved.
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