Liquid chromatographic resolution of proton pump inhibitors including omeprazole on a ligand exchange chiral stationary phase |
| |
Authors: | Jin Joo Ha Hee Jung Choi Jong Sung Jin Euh Duck Jeong Myung Ho Hyun |
| |
Affiliation: | 1. Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Kuemjeong-Ku, Busan 609-735, South Korea;2. High-Technology Components & Materials Research Center & Busan Center, Korea Basic Science Institute (KBSI), Busan 609-735, South Korea |
| |
Abstract: | A ligand exchange chiral stationary phase (CSP) developed previously in this laboratory by bonding (R)-phenylglycinol derivative, sodium N-[(R)-2-hydroxy-1-phenylethyl]-N-undecylaminoacetate, to silica gel was successfully applied to the resolution of proton pump inhibitors (PPIs) including omeprazole, pantoprazole, lansoprazole and rabeprazole. For example, the separation factors (α) for the resolution of omeprazole, pantoprazole, lansoprazole and rabeprazole were 4.27, 5.28, 2.77 and 4.06, respectively, and the resolutions (RS) were 2.53, 2.55, 1.93, and 2.01, respectively, when 65% acetonitrile aqueous solution containing 0.5 mM CuSO4 and 0.05 mM triethylamine was used as a mobile phase. Based on the chromatographic behaviors for the resolution of PPI analogues on CSP 1, a chiral recognition mechanism utilizing the sulfoxide oxygen and the benzimidazole ring nitrogen of PPIs as bidentate coordination donors to form an enantioselective ternary complex with the central Cu(II) ion and the chiral stationary bidentate ligand was proposed. |
| |
Keywords: | Enantiomer separation Ligand exchange chiral stationary phase Liquid chromatography Omeprazole Proton pump inhibitor |
本文献已被 ScienceDirect 等数据库收录! |
|