title: Chiral separation of short chain aliphatic hydroxycarboxylic acids on cinchonan carbamate-based weak chiral anion exchangers and zwitterionic chiral ion exchangers.
abstract: Chiral short chain aliphatic hydrocarboxylic acids (HCAs) are common compounds being part of different biological processes. In order to control and understand these processes is of pivotal importance to determine the identity of the involved enantiomer or their enantiomeric ratio. In this study the capacity of quinine- and quinidine-derived chiral stationary phases to perform the enantioseparation of eight chiral HCAs (tartaric acid, isocitric acid, malic acid, glyceric acid, 2-hydroxyglutaric acid, 2-hydroxybutyric acid, lactic acid and 3-hydroxybutyric acid) was evaluated. MS-compatible conditions consisting of ACN/MeOH mixtures as eluents with formic acid, acetic acid and/or their ammonium salts as additives, temperatures between 10 and 25°C (except for -20°C for 3-hydroxybutyric acid) and a flow rate of 1.00mL/min yielded full baseline resolution for all studied HCAs. Elution order for the HCA enantiomers was determined revealing different behaviors between the studied compounds.
authors.affiliation: Institute of Pharmaceutical Sciences, Pharmaceutical (Bio-)Analysis, University of Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany.
authors.forename: Carlos
authors.initials: C
authors.lastname: Calderón
authors.affiliation: Institute of Pharmaceutical Sciences, Pharmaceutical (Bio-)Analysis, University of Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany. Electronic address: michael.laemmerhofer@uni-tuebingen.de.
authors.forename: Michael
authors.initials: M
authors.lastname: Lämmerhofer
mesh_terms: D020155:3-Hydroxybutyric Acid / Q000302:isolation & purification; D000837:Anion Exchange Resins / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D002852:Chromatography, Ion Exchange / Q000379:methods*; D005227:Fatty Acids / Q000737:chemistry / Q000302:isolation & purification; D006880:Hydroxy Acids / Q000737:chemistry / Q000302:isolation & purification*; D007475:Ion Exchange Resins / Q000737:chemistry*; D011802:Quinidine / Q000737:chemistry; D011803:Quinine / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000837:Anion Exchange Resins; D002219:Carbamates; D005227:Fatty Acids; D006880:Hydroxy Acids; D007475:Ion Exchange Resins; D011803:Quinine; D011802:Quinidine; D020155:3-Hydroxybutyric Acid
keywords: Chiral ion-exchangers; Enantioselective chromatography; Enantioselective metabolomics; Zwitterionic ion-exchangers; cryo-HPLC; α- and β -Hydroxycarboxylic acid