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New chiral stationary phases for liquid chromatography based on small molecules: Development, enantioresolution evaluation and chiral recognition mechanisms
Author(s) -
Phyo Ye' Zaw,
Teixeira Joana,
Tiritan Maria Elizabeth,
Cravo Sara,
Palmeira Andreia,
Gales Luís,
Silva Artur M.S.,
Pinto Madalena M.M.,
Kijjoa Anake,
Fernandes Carla
Publication year - 2020
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23142
Subject(s) - chemistry , enantioselective synthesis , benzophenone , chiral stationary phase , chromatography , molecule , chiral derivatizing agent , chiral column chromatography , high performance liquid chromatography , combinatorial chemistry , organic chemistry , catalysis
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.