title: Computational prediction of diastereomeric separation behavior of fluorescent o-phthalaldehyde derivatives of amino acids.
abstract: We have developed a convenient method for predicting the LC resolution of amino acid diastereomers through computational calculations. For acquiring experimental data, we derivatized 10 amino acids using o-phthalaldehyde and N-acetyl-L-cysteine as fluorogenic diastereomer-forming reagents and analyzed the diastereomers using reversed-phase LC and fluorescence detection. For theoretical chemical calculations, we used the publicly available semi-empirical calculation software MOPAC2012. Using the obtained experimental and theoretical data, we determined the change in analytical resolution with differences in the structure of the diastereomers. From the results obtained, we concluded that greater conformational change through diastereomeric derivatization induced an increase in the contact area with the stationary phase, leading to higher resolution.
authors.affiliation: Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka.
authors.forename: Kenichiro
authors.initials: K
authors.lastname: Todoroki
authors.forename: Tatsuki
authors.initials: T
authors.lastname: Nakano
authors.forename: Hiroki
authors.initials: H
authors.lastname: Watanabe
authors.forename: Jun Zhe
authors.initials: JZ
authors.lastname: Min
authors.forename: Koichi
authors.initials: K
authors.lastname: Inoue
authors.forename: Yoshinobu
authors.initials: Y
authors.lastname: Ishikawa
authors.forename: Toshimasa
authors.initials: T
authors.lastname: Toyo'oka
mesh_terms: D000111:Acetylcysteine / Q000737:chemistry; D000596:Amino Acids / Q000032:analysis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D005456:Fluorescent Dyes / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D012984:Software; D013237:Stereoisomerism; D009764:o-Phthalaldehyde / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D005456:Fluorescent Dyes; D009764:o-Phthalaldehyde; D000111:Acetylcysteine