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

Salma Al-Kindy, Tomofumi Santa, Takeshi Fukushima, Hiroshi Homma, Kazuhiro Imai

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

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 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.

Original languageEnglish
Pages (from-to)276-280
Number of pages5
JournalBiomedical Chromatography
Volume12
Issue number5
DOIs
Publication statusPublished - Sep 1998

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High performance liquid chromatography
Amines
High Pressure Liquid Chromatography
Derivatives
Enantiomers
Proline
Alanine
Methanol
Chemical activation
Temperature
triphenylphosphine
2,2'-dipyridyl disulfide
acetonitrile

ASJC Scopus subject areas

  • Analytical Chemistry
  • Clinical Biochemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Pharmacology

Cite this

Enantiomeric determination of amines by high-performance liquid chromatography using chiral fluorescent derivatization reagents. / Al-Kindy, Salma; Santa, Tomofumi; Fukushima, Takeshi; Homma, Hiroshi; Imai, Kazuhiro.

In: Biomedical Chromatography, Vol. 12, No. 5, 09.1998, p. 276-280.

Research output: Contribution to journalArticle

Al-Kindy, Salma ; Santa, Tomofumi ; Fukushima, Takeshi ; Homma, Hiroshi ; Imai, Kazuhiro. / Enantiomeric determination of amines by high-performance liquid chromatography using chiral fluorescent derivatization reagents. In: Biomedical Chromatography. 1998 ; Vol. 12, No. 5. pp. 276-280.
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abstract = "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 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.",
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AB - 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 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.

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