Application of optically pure amines as chiral auxiliaries to develop trichloro-s-triazine-based new chiral derivatizing reagents for reversed-phase high-performance liquid chromatographic enantioseparation of dl-selenomethionine

(R)-(+)-naphthylethyl amine and (S)-(+)-1-benzyl-3-aminopyrrolidine were incorporated as chiral auxiliaries, by nucleophilic substitution of chlorine atoms, in cyanuric chloride (CC) or its 6-butoxy derivative. There were obtained four new chiral derivatizing reagents (CDRs) as two dichloro and two monochloro triazine reagents. The CDRs so obtained were characterized and their optical purity was ascertained. Diastereomers of dl-selenomethionine were synthesized under microwave irradiation for 60 or 90s (at 80% power of 800W). Reversed-phase high-performance liquid chromatographic separation of diastereomers was carried out on a C-18 column using mixtures of acetonitrile with aqueous trifluoroacetic acid as mobile phase. The detection was made at 230nm using a photodiode array detector. The separation behaviors in terms of retention times and resolutions were compared. The separation method was validated for limit of detection, linearity, accuracy, precision, and recovery. Copyright (c) 2013 John Wiley & Sons, Ltd.