title: 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride as an enantioseparation enhancer for fluorescence chiral derivatization-liquid chromatographic analysis of dl-lactic acid.
abstract: This paper reports a novel fluorescence chiral derivatization-liquid chromatography (LC) method for the analysis of d- and l-lactic acids (LAs) using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as an enantioseparation enhancer. In this method, the dl-LAs were fluorescently derivatized with (S)-(+)-4-(N,N-dimethylaminosulfonyl)-7-(3-aminopyrrolidin-1-yl)-2,1,3-benzoxadiazole [(S)-(+)-DBD-APy] in the presence of DMT-MM as a condensing agent. These conditions resulted in the hydroxyl group of the LA derivative being etherified by the triazine unit of DMT-MM, producing sterically bulky diastereoisomers. The resulting fluorescent diastereoisomers of d- and l-LAs could be discriminated and successfully enantioseparated through reversed-phase LC. The enhancement effect of the derivatization agent DMT-MM when using seven other commercially available chiral amines was also demonstrated. Finally, this method was successfully applied to quantification of dl-LAs in foodstuffs (yogurts and fermented milk drinks).
authors.affiliation: Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors.forename: Kenichiro
authors.initials: K
authors.lastname: Todoroki
authors.affiliation: Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors.forename: Kanoko
authors.initials: K
authors.lastname: Goto
authors.affiliation: Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors.forename: Tatsuki
authors.initials: T
authors.lastname: Nakano
authors.affiliation: Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Ishii
authors.affiliation: Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors.forename: Jun Zhe
authors.initials: JZ
authors.lastname: Min
authors.affiliation: Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors.forename: Koichi
authors.initials: K
authors.lastname: Inoue
authors.affiliation: Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan. Electronic address: toyooka@u-shizuoka-ken.ac.jp.
authors.forename: Toshimasa
authors.initials: T
authors.lastname: Toyo'oka
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D005453:Fluorescence; D019344:Lactic Acid / Q000032:analysis*; D008958:Models, Molecular; D009025:Morpholines / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism
chemical_list: C467606:4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; D009025:Morpholines; D019344:Lactic Acid
keywords: Chiral derivatization; DMT-MM; Enantioseparation enhancer; Fluorescence; dl-Lactic acid