title: Enantioseparation and chiral recognition mechanism of new chiral derivatives of xanthones on macrocyclic antibiotic stationary phases.
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.
authors.affiliation: Centro de Química Medicinal da Universidade do Porto-CEQUIMED-UP, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal.
authors.forename: Carla
authors.initials: C
authors.lastname: Fernandes
authors.forename: Maria Elizabeth
authors.initials: ME
authors.lastname: Tiritan
authors.forename: Quezia
authors.initials: Q
authors.lastname: Cass
authors.forename: Visvaldas
authors.initials: V
authors.lastname: Kairys
authors.forename: Miguel Xavier
authors.initials: MX
authors.lastname: Fernandes
authors.forename: Madalena
authors.initials: M
authors.lastname: Pinto
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation* / Q000379:methods; D006020:Glycopeptides / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000737:chemistry*; D008958:Models, Molecular; D013237:Stereoisomerism; D013816:Thermodynamics; D044004:Xanthones / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D000900:Anti-Bacterial Agents; D006020:Glycopeptides; D047028:Macrocyclic Compounds; D044004:Xanthones