title: Development of an improved ligand exchange chiral stationary phase based on leucinol for the resolution of proton pump inhibitors.
abstract: As an effort to develop improved ligand exchange chiral stationary phases (CSPs) for the resolution of chiral drugs, the residual silanol groups on the silica surface of a CSP based on sodium N-[(S)-1-hydroxymethyl-3-methylbutyl]-N-undecylaminoacetate, a (S)-leucinol derivative, were protected with n-octyl groups. The residual silanol group-protected CSP was applied to the resolution of proton pump inhibitors (PPIs) such as omeprazole, pantoprazole, lansoprazole and rabeprazole. The resolution of PPIs on the residual silanol group-protected CSP was excellent with the separation factors (α) in the range of 4.32-6.42 and the resolution factors (RS) in the range of 6.70-7.15. The improved chiral recognition ability of the residual silanol group-protected CSP was rationalized to be originated from the protection of the non-enantioselective interaction sites on the silica surface and the improved lipophilicity of the stationary phase.
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, Republic of Korea.
authors.forename: Jin Joo
authors.initials: JJ
authors.lastname: Ha
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, Republic of Korea.
authors.forename: Hye Jee
authors.initials: HJ
authors.lastname: Han
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, Republic of Korea.
authors.forename: Hee Eun
authors.initials: HE
authors.lastname: Kim
authors.affiliation: Division of High Technology Materials Research, Busan Center, Korea Basic Science Institute (KBSI), Busan 618-230, Republic of Korea.
authors.forename: Jong Sung
authors.initials: JS
authors.lastname: Jin
authors.affiliation: Division of High Technology Materials Research, Busan Center, Korea Basic Science Institute (KBSI), Busan 618-230, Republic of Korea.
authors.forename: Euh Duck
authors.initials: ED
authors.lastname: Jeong
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, Republic of Korea. Electronic address: mhhyun@pusan.ac.kr.
authors.forename: Myung Ho
authors.initials: MH
authors.lastname: Hyun
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D007930:Leucine / Q000031:analogs & derivatives* / Q000737:chemistry; D008024:Ligands; D054328:Proton Pump Inhibitors / Q000302:isolation & purification*; D058428:Silica Gel; D013237:Stereoisomerism; D013499:Surface Properties
chemical_list: D008024:Ligands; D054328:Proton Pump Inhibitors; D058428:Silica Gel; C417575:leucinol; D007930:Leucine
keywords: Chiral stationary phase; Enantiomer separation; Ligand exchange; Liquid chromatography; Proton pump inhibitors