title: Direct high-performance liquid chromatographic enantioseparation of free α-, β- and γ-aminophosphonic acids employing cinchona-based chiral zwitterionic ion exchangers.
abstract: We report a chiral high-performance liquid chromatographic enantioseparation method for free α-aminophosphonic, β-aminophosphonic, and γ-aminophosphonic acids, aminohydroxyphosphonic acids, and aromatic aminophosphinic acids with different substitution patterns. Enantioseparation of these synthons was achieved by means of high-performance liquid chromatography on CHIRALPAK ZWIX(+) and ZWIX(-) (cinchona-based chiral zwitterionic ion exchangers) under polar organic chromatographic elution conditions. Mobile phase characteristics such as acid-to-base ratio, type of counterion, and solvent composition were systematically varied in order to investigate their effect on the separation performance and to achieve optimal separation conditions for the set of analytes. Under the optimized conditions, 32 of 37 racemic aminophosphonic acids studied reached baseline separation when we employed a single generic mass-spectrometry-compatible mobile phase, with reversal of the elution order when we used (+) and (-) versions of the chiral stationary phase.
authors.affiliation: Department of Analytical Chemistry, University of Vienna, Waehringer Strasse 38, 1090, Vienna, Austria.
authors.forename: Andrea F G
authors.initials: AF
authors.lastname: Gargano
authors.forename: Michal
authors.initials: M
authors.lastname: Kohout
authors.forename: Pavla
authors.initials: P
authors.lastname: Macíková
authors.forename: Michael
authors.initials: M
authors.lastname: Lämmerhofer
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Lindner
mesh_terms: D000596:Amino Acids / Q000737:chemistry / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D002852:Chromatography, Ion Exchange / Q000379:methods*; D002929:Cinchona / Q000737:chemistry; D007475:Ion Exchange Resins / Q000737:chemistry*; D010757:Phosphorous Acids / Q000737:chemistry / Q000302:isolation & purification*; D011802:Quinidine / Q000737:chemistry*; D011803:Quinine / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D007475:Ion Exchange Resins; D010757:Phosphorous Acids; D011803:Quinine; D011802:Quinidine