Enantiomeric determination of amines by high-performance liquid chromatography using chiral fluorescent derivatization reagents

✍ Scribed by Salma Al-Kindy; Tomofumi Santa; Takeshi Fukushima; Hiroshi Homma; Kazuhiro Imai

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 114 KB
• Volume: 12
• Category: Article
• ISSN: 0269-3879
• DOI: 10.1002/(sici)1099-0801(199809/10)12:5<276::aid-bmc747>3.0.co;2-y

✦ Synopsis

4-(2-carboxypyrrolidin-1-yl)-7-nitro-2,1,3-benzoxadiazole (NBD-Pro), 4-(2-carboxypyrrolidin-1-yl)-7-(N,N-dimethylamino-sulphonyl)-2,1,3 - benzoxadiazole DBD-Pro), 4-(N-1-carboxyethyl-N-methyl)amino-7-nitro-2,1,3-benzoxadiazole NBD-N-Me-Ala), 4-(N-1-carboxyethyl-N-methyl) amino-7-(N,N-dimethylamino-2,1,3-benzoxadiazole. (DBD-N-Me-Ala) have been synthesized for the resolution of enantiomers of amines by high performance liquid chromatography (HPLC). The reagents react with amino group at room temperature in the presence of activation agents, 2,2'-dipyridyl disulphide (DPDS) and triphenylphosphine (TPP) to produce the corresponding diastereomers. The derivatives were detected at lambda ex = 469, lambda em = 569 for DBD-moeity and lambda ex = 469, lambda em = 535 for NBD moeity. The resulting diastereomers were efficiently resolved using reversed-phase column with aqueous acetonitrile and aqueous methanol as the mobile phase. The elution order of the derivatives were D and L when proline was used as the chiral selector but the order was reversed when the diastereomers were prepared with the reagent containing N-methyl alanine as the chiral selector. DBD-Pro and NBD-Pro seem to give better separation as compared to DBD-N-Me-Ala and NBD-N-Me-Ala.