title: Advanced dress-up chiral columns: New removable chiral stationary phases for enantioseparation of chiral carboxylic acids.
abstract: This paper describes the preparation of new dress-up columns featuring reproducibly removable and replaceable chiral stationary phases. After synthesizing perfluroalkylated quinine and quinidine derivatives as chiral stationary phase compounds (F-CSPs), we adsorbed them reversibly onto a fluorous LC column through pumping of their solutions. Using this dress-up chiral column and fluorophobic elution of aqueous ammonium formate/MeOH mixtures, we could enantioseparate four racemic N-acetyl amino acids, dichlorprop, and sixteen fluorescent 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC)-derivatized amino acids. Dressing and undressing of the coated F-CSPs could be controlled by varying the fluorophilicity and fluorophobicity of the eluent. The relative standard deviations of the retention times, the retention factors, the number of theoretical plates, the enantioseparation factors, and the resolutions of each of four preparations of such dress-up columns were all less than or equal to 5.26% (from 20 repeated analyses); the reproducibilities from four different preparations were all less than or equal to 10.6%. These columns also facilitated highly sensitive and selective analyses of AQC-amino acids when detected using LC-MS/MS.
authors.affiliation: Department of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan.
authors.forename: Kenichiro
authors.initials: K
authors.lastname: Todoroki
authors.affiliation: Department of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan.
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Ishii
authors.affiliation: Department of Synthetic Organic Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan.
authors.forename: Takafumi
authors.initials: T
authors.lastname: Ide
authors.affiliation: Department of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan.
authors.forename: Jun Zhe
authors.initials: JZ
authors.lastname: Min
authors.affiliation: Department of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan.
authors.forename: Koichi
authors.initials: K
authors.lastname: Inoue
authors.affiliation: Department of Chemistry, University of Massachusetts, Boston, MA 02125, USA.
authors.forename: Xin
authors.initials: X
authors.lastname: Huang
authors.affiliation: Department of Chemistry, University of Massachusetts, Boston, MA 02125, USA.
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.affiliation: Department of Synthetic Organic Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan.
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Hamashima
authors.affiliation: Department of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan. Electronic address: toyooka@u-shizuoka-ken.ac.jp.
authors.forename: Toshimasa
authors.initials: T
authors.lastname: Toyo'oka
mesh_terms: D000596:Amino Acids / Q000032:analysis; D002264:Carboxylic Acids / Q000737:chemistry / Q000302:isolation & purification*; D002853:Chromatography, Liquid / Q000295:instrumentation*; D005456:Fluorescent Dyes / Q000737:chemistry; D015203:Reproducibility of Results; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism; D053719:Tandem Mass Spectrometry
chemical_list: D000596:Amino Acids; D002264:Carboxylic Acids; D005456:Fluorescent Dyes
keywords: Chiral carboxylic acids; Cinchona alkaloids; Dress-up chiral column; Fluorous separation