title: Dress-up chiral columns for the enantioseparation of amino acids based on fluorous separation.
abstract: In this paper, we report a new type of chiral high-performance liquid chromatography (HPLC) column--a so-called dress-up chiral column--featuring a chiral stationary phase adsorbed reversibly in a commercial fluorous HPLC column through fluorous interactions. We synthesized perfluroalkylated proline derivatives as chiral stationary phase compounds and then adsorbed them reversibly in the fluorous HPLC column through the pumping of their solutions. By using this dress-up chiral column and fluorophobic elution of an aqueous copper(II) sulfate/MeOH mixture, we could enantioseparate seven racemic amino acids within 40 min. When we washed the dress-up chiral column with fluorophilic tetrahydrofuran or MeOH, the adsorbed chiral stationary phase compounds desorbed from the column, completely destroying its enantioseparation ability. The relative standard deviation of the retention times, the number of theoretical plates, and the resolution for each of four preparations of the dress-up columns were all less than or equal to 9.53% in 20-times repeated analysis, and were all less than or equal to 18.7% in four different preparations, respectively.
authors.affiliation: Department of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, Shizuoka, 422-8526, Japan.
authors.forename: Kenichiro
authors.initials: K
authors.lastname: Todoroki
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Ishii
authors.forename: Koji
authors.initials: K
authors.lastname: Toyoda
authors.forename: Takashi
authors.initials: T
authors.lastname: Ikawa
authors.forename: Jun Zhe
authors.initials: JZ
authors.lastname: Min
authors.forename: Koichi
authors.initials: K
authors.lastname: Inoue
authors.forename: Shuji
authors.initials: S
authors.lastname: Akai
authors.forename: Toshimasa
authors.initials: T
authors.lastname: Toyo'oka
mesh_terms: D000327:Adsorption; D000596:Amino Acids / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D019327:Copper Sulfate / Q000737:chemistry; D054879:Halogenation; D011392:Proline / Q000031:analogs & derivatives*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D011392:Proline; D019327:Copper Sulfate