Liquid chromatographic resolution of proton pump inhibitors including omeprazole on a ligand exchange chiral stationary phase.
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 (R(S)) were 2.53, 2.55, 1.93, and 2.01, respectively, when 65% acetonitrile aqueous solution containing 0.5mM CuSO(4) and 0.05mM 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.
Ha
Jin Joo
JJ
Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Kuemjeong-Ku, Busan 609-735, South Korea.
Choi
Hee Jung
HJ
Jin
Jong Sung
JS
Jeong
Euh Duck
ED
Hyun
Myung Ho
MH
D000097:Acetonitriles; D002853:Chromatography, Liquid / Q000379:methods*; D019327:Copper Sulfate; D005021:Ethylamines; D006863:Hydrogen-Ion Concentration; D009853:Omeprazole / Q000737:chemistry*; D054328:Proton Pump Inhibitors / Q000737:chemistry*; D015203:Reproducibility of Results; D012680:Sensitivity and Specificity; D013237:Stereoisomerism
D000097:Acetonitriles; D005021:Ethylamines; D054328:Proton Pump Inhibitors; D009853:Omeprazole; D019327:Copper Sulfate; C016162:triethylamine; C032159:acetonitrile