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New chiral stationary phases for liquid chromatography based on small molecules: Development,enantioresolution evaluation and chiral recognition mechanisms |
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| Authors: | Ye' Zaw Phyo Joana Teixeira Maria Elizabeth Tiritan Sara Cravo Andreia Palmeira Luís Gales Artur MS Silva Madalena MM Pinto Anake Kijjoa Carla Fernandes |
| Institution: | 1. ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Porto, Portugal
Interdisciplinary Centre of Marine and Environmental Research, CIIMAR, Matosinhos, Portugal;2. Faculdade de Farmácia, Departamento de Ciências Químicas, Laboratório de Química Orgânica e Farmacêutica, Porto, Portugal;3. Interdisciplinary Centre of Marine and Environmental Research, CIIMAR, Matosinhos, Portugal;4. Interdisciplinary Centre of Marine and Environmental Research, CIIMAR, Matosinhos, Portugal Faculdade de Farmácia, Departamento de Ciências Químicas, Laboratório de Química Orgânica e Farmacêutica, Porto, Portugal;5. ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Porto, Portugal Instituto de Biologia Molecular e Celular (IBMC), Universidade do Porto, Porto, Portugal i3S – Instituto de Investigação e Inovação em Saúde, Porto, Portugal;6. QOPNA & LAQV-REQUIMTE, Departamento de Química, Universidade de Aveiro, Aveiro, Portugal |
| Abstract: | Recently, we reported the development of new chiral stationary phases (CSPs) for liquid chromatography (LC) based on chiral derivatives of xanthones (CDXs). Based on the most promising CDX selectors, 12 new CSPs were successfully prepared starting from suitable functionalized small molecules including xanthone and benzophenone derivatives. The chiral selectors comprising one, two, three, or four chiral moieties were covalently bonded to a chromatographic support and further packed into LC stainless-steel columns (150 × 2.1 mm I.D.). The enantioselective performance of the new CSPs was evaluated by LC using different classes of chiral compounds. Specificity for enantioseparation of some CDXs was observed in the evaluation of the new CSPs. Besides, assessment of chiral recognition mechanisms was performed by computational studies using molecular docking approach, which are in accordance with the chromatographic parameters. X-Ray analysis was used to establish a chiral selector 3D structure. |
| Keywords: | benzophenone chiral derivative of xanthone chiral recognition chiral stationary phase docking enantioselectivity liquid chromatography |