Ritalin, [(+)-threo]methylphenidate hydrochloride, is a chiral drug substance with two chiral centers. The drug substance may contain three pairs of enantiomers, [(+)-threo], [(-)-threo], [(+)-erythro] and [(-)-erythro] isomers, and its degradation products, threoritalinic acid racemate. Determination of the optical purity of ritalin drug substance and the amount of its by-product isomers is a critical step in the single-isomer drug development. In order to efficiently recognize the three pairs of enantiomers by one method, capillary electrophoresis (CE) was employed for the separation. The three pairs of enantiomers in CE showed different enantioselectivities with eight different types of CDs. Only 2,6-di-o-methyl-beta-cyclodextrin (DM-beta-CD) and carboxymethyl-beta-cyclodextrin (CM-beta-CD) showed enantioselectivity to all these pairs of enantiomers. With respect to separation resolution and efficiency, DM-beta-CD was chosen as the chiral selector. For optimization of the separation conditions, the concentration of DM-beta-CD, pH of the buffer solution, and temperature of the capillary were further studied.
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http://dx.doi.org/10.1002/1522-2683(200109)22:15<3226::AID-ELPS3226>3.0.CO;2-V | DOI Listing |
Sci Total Environ
January 2025
US Department of Agriculture, Agriculture Research Service, Hydrology and Remote Sensing Laboratory, Beltsville, MD, United States of America.
Metolachlor is the most heavily used member of acetanilide herbicides, which are noted for forming highly soluble metabolites in root zone soils soon after field application. The two primary metabolites of metolachlor, metolachlor ethane sulfonic acid (MESA) and metolachlor oxanilic acid (MOXA), retain the same chiral chemistry as their source and are important tracers of nitrate loading from agricultural cropland. New analytical methods for separating the isomers of MESA and MOXA, enable studies assessing changes in the abundance of atropisomer pairs of the carbon chiral enantiomers in environmental samples.
View Article and Find Full Text PDFMolecules
January 2025
Department of Pharmacy, Jilin Medical University, Jilin 132013, China.
An efficient stereoselective synthesis of 10-hydroxy-10-(1-indol-3-yl)-9-(10)-phenanthrene derivatives was realized through an organocatalyzed Friedel-Crafts reaction of phenanthrenequinones and indoles using a (,)-dimethylaminocyclohexyl-squaramide as the catalyst. Under the optimized conditions, the desired chiral products were obtained in good yields (73-90%) with moderate to high ee values (up to 97% ee). Two pairs of synthesized enantiomers were subjected to evaluation of their antiproliferative activities on four types of human cancer cell lines and one human umbilical vein endothelial cell line using the CCK-8 assay.
View Article and Find Full Text PDFChemistry
January 2025
Nanjing University of Posts and Telecommunications, Institute of Advanced Materials (IAM), 9 Wenyuan Road, Nanjing 210023, China., Nanjing, CHINA.
Circularly polarized organic light-emitting diodes (CP-OLEDs) have significant promise for naked-eye 3D displays. However, most devices are fabricated using vacuum deposition technology, and development of efficient solution-processed CP-OLEDs, particularly those exhibiting low efficiency roll-off, remains a formidable challenge. This research successfully designed and synthesized two pairs of thermally activated delayed fluorescence (TADF) enantiomers through isomer engineering, namely (R/S)-N-5-TPA and (R/S)-N-4-TPA, which features fifth and fourth substitution sites of phthalimide (acceptor) by tri-phenylamine (donor), respectively.
View Article and Find Full Text PDFCryst Growth Des
January 2025
School of Chemistry, Analytical and Biological Chemistry Research Facility, SSPC, the SFI Research Centre for Pharmaceuticals, University College Cork, Cork T12 K8AF, Ireland.
The crystal structures of (±)-mandelamide, -mandelamide, and enantioenriched mandelamide (94 : 6 ) were determined. Diastereomeric cocrystal pairs of -mandelamide with both enantiomers of mandelic acid and proline were synthesized. The diastereomeric cocrystal pairs of -mandelamide with /-mandelic acid form 1:1 cocrystals in each case, while the diastereomeric cocrystal pairs of -mandelamide with proline have different stoichiometries.
View Article and Find Full Text PDFPhytochemistry
December 2024
Henan Province Hospital of Traditional Chinese Medicine, No. 6, Dongfeng Road, Jinshui District, Zhengzhou City, Henan Province, 450002, China. Electronic address:
Five phenylpropanoid dimers chrysanthephenyls A-E, with the 1-O-1'-type (1) and 1-O-2'-type (2-5) ether bond linking modes, were isolated from the aerial parts of Chrysanthemum indicum. Among them, chrysanthephenyls D and E were two pairs of enantiomers, and chrysanthephenyl E was further resolved into its enantiomers (+)-chrysanthephenyl E and (-)-chrysanthephenyl E via chiral-phase HPLC. Their structures were characterized on the basic analysis of the spectroscopic techniques (IR, HRESIMS, 1D and 2D NMR), and their absolute configurations were determined by DP4+ NMR analysis and ECD calculation method.
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