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Enantiomeric determination of amines by high‐performance liquid chromatography using chiral fluorescent derivatization reagents
Author(s) -
AlKindy Salma,
Santa Tomofumi,
Fukushima Takeshi,
Homma Hiroshi,
Imai Kazuhiro
Publication year - 1998
Publication title -
biomedical chromatography
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.4
H-Index - 65
eISSN - 1099-0801
pISSN - 0269-3879
DOI - 10.1002/(sici)1099-0801(199809/10)12:5<276::aid-bmc747>3.0.co;2-y
Subject(s) - chemistry , diastereomer , reagent , enantiomer , high performance liquid chromatography , chromatography , derivatization , aqueous solution , elution , amino acid , methanol , medicinal chemistry , organic chemistry , biochemistry
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 λ ex = 469, λ em = 569 for DBD‐moeity and λ ex = 469, λ 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 DL 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. © 1998 John Wiley & Sons, Ltd.