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Immobilization of Chondroitin Sulfate A onto Monolithic Epoxy Silica Column as a New Chiral Stationary Phase for High-Performance Liquid Chromatographic Enantioseparation

ORCID
0000-0002-9308-2281
Affiliation
Institute of Medicinal and Pharmaceutical Chemistry, Technische Universität Braunschweig
Ratih, Ratih;
GND
121081796
Affiliation
Institute of Medicinal and Pharmaceutical Chemistry, Technische Universität Braunschweig
Wätzig, Hermann; Azminah, Azminah; Asmari, Mufarreh; Peters, Benjamin;
ORCID
0000-0001-6417-4737
Affiliation
Institute of Medicinal and Pharmaceutical Chemistry, Technische Universität Braunschweig
El Deeb, Sami

Chondroitin sulfate A was covalently immobilized onto a monolithic silica epoxy column involving a Schiff base formation in the presence of ethylenediamine as a spacer and evaluated in terms of its selectivity in enantioseparation. The obtained column was utilized as a chiral stationary phase in enantioseparation of amlodipine and verapamil using a mobile phase consisting of 50 mM phosphate buffer pH 3.5 and UV detection. Sample dilution by organic solvents (preferably 25% v/v acetonitrile-aqueous solution) was applied to achieve baseline enantioresolution (Rs > 3.0) of the individual drug models within 7 min, an excellent linearity (R2 = 0.999) and an interday repeatability of 1.1% to 1.8% RSD. The performance of the immobilized column for quantification of racemate in commercial tablets showed a recovery of 86-98% from tablet matrices. Computational modeling by molecular docking was employed to investigate the feasible complexes between enantiomers and the chiral selector.

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