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Direct HPLC separation of enantiomers of pantoprazole and other benzimidazole sulfoxides using cellulose‐based chiral stationary phases in reversed‐phase mode
Author(s) -
Tanaka Makoto,
Yamazaki Hideki,
Hakusui Hideo
Publication year - 1995
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.530070810
Subject(s) - chemistry , enantiomer , pantoprazole , benzimidazole , chiral stationary phase , chromatography , high performance liquid chromatography , cellulose , chiral column chromatography , phase (matter) , chiral derivatizing agent , stationary phase , sulfoxide , organic chemistry , pharmacology , medicine , omeprazole
A direct, isocratic, and simple reversed‐phase HPLC method was described for the separation of enantiomers of the proton pump inhibitor, rac‐pantoprazole (PAN) using cellulose‐based chiral stationary phases (Chiralcel OD‐R and Chiralcel OJ‐R). Some structurally related chiral benzimidazole sulfoxides, rac‐omeprazole (OME) and raclansoprazole (LAN), were also studied. Chiralcel OJ‐R was successful in the resolution of enantiomers of rac‐PAN and rac‐OME, while Chiralcel OD‐R was most suitable for resolving the enantiomers of rac‐LAN. Highest enantioselectivity to rac‐PAN and rac‐OME was achieved on Chiralcel OJ‐R by using acetonitrile as an organic modifier, whereas methanol afforded better resolution of rac‐LAN on Chiralcel OD‐R than acetonitrile. Increases in buffer concentration and column temperature decreased retention and did not improve the resolution of the enantiomers on both columns. Using a mixture of 50 m M sodium perchlorate solution and acetonitrile as a mobile phase at a flow rate of 0.5 ml/min, maximum separation factors of 1.26 and 1.13 were obtained for the enantiomers of rac‐PAN and rac‐OME using a Chiralcel OJ‐R column, while maximum separation factor of 1.16 was obtained for the enantiomers of rac‐LAN using a Chiralcel OD‐R column. © 1995 Wiley‐Liss, Inc.