title: Simultaneous determination of diastereoisomeric and enantiomeric impurities in SSS-octahydroindole-2-carboxylic acid by chiral high-performance liquid chromatography with pre-column derivatization.
abstract: SSS-Octahydroindole-2-carboxylic acid (SSS-Oic) is a key intermediate used in the synthesis of some angiotensin-converting enzyme (ACE) inhibitors. The separation of diastereoisomers and enantiomers of Oic was performed using a pre-column derivatization chiral HPLC method. Phenyl isothiocyanate (PITC) was used as the derivatization reagent. Three PITC derivatives of Oic stereoisomers were separated on an Ultron ES-OVM chiral column (150 mm x 4.6 mm, 5 microm). Derivatization conditions such as reaction temperature, reaction time and derivatization reagent concentration were investigated. The chromatographic conditions for separation of the three PITC-Oic derivatives were optimized. The method was successfully applied in the diastereoisomeric and enantiomeric purity test of SSS-Oic.
authors.affiliation: Department of Pharmaceutical Analysis and Drug Metabolism, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Zhejiang, China.
authors.forename: Jin Zhao
authors.initials: JZ
authors.lastname: Wang
authors.forename: Su
authors.initials: S
authors.lastname: Zeng
authors.forename: Gong Yun
authors.initials: GY
authors.lastname: Hu
authors.forename: Dan Hua
authors.initials: DH
authors.lastname: Wang
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D000806:Angiotensin-Converting Enzyme Inhibitors / Q000138:chemical synthesis; D002264:Carboxylic Acids / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D004340:Drug Contamination / Q000517:prevention & control; D004355:Drug Stability; D006863:Hydrogen-Ion Concentration; D007211:Indoles / Q000737:chemistry*; D016014:Linear Models; D012680:Sensitivity and Specificity; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D000097:Acetonitriles; D000806:Angiotensin-Converting Enzyme Inhibitors; D002264:Carboxylic Acids; D007211:Indoles; C543265:octahydroindole-2-carboxylic acid; C032159:acetonitrile