1-(5-Dimethylamino-1-naphthalenesulphonyl)-(S)- 3-aminopyrrolidine (DNS-Apy) as a fluorescence chiral labelling reagent for carboxylic acid enantiomers

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

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

1-(5-Dimethylamino-1-naphthalenesulphonyl)-(S)-3-aminopyrrolidine (DNS-Apy) has been synthesized for the separation of carboxylic acid enantiomers by high-performance liquid chromatography (HPLC) and sensitive detection. The reagent reacts with carboxylic acids at room temperature in the presence of activation agents 2,2'-dipyridyl disulphide (DPDS) and triphenylphosphine (TPP). The maximum emission of the diastereomeric amide derived from (S)-phenylpropionic acid and ketoprofen derivatives of DNS-Apy was at 530 nm with excitation at 340 nm. The emission wavelength shifted towards the blue and the fluorescence intensities increased with increasing acetonitrile concentration in the medium. The diastereomers derived from anti-inflammatory drugs were efficiently resolved with a reverse-phase column using water:acetonitrile mixture as mobile phase. All of the racemate of arylpropionic acid derivatives gave equal fluorescence intensity of the two enantiomers with the exception of ketoprofen derivatives where the intensity of the first eluting enantiomer was half that of the second.

Original languageEnglish
Pages (from-to)137-142
Number of pages6
JournalBiomedical Chromatography
Volume11
Issue number3
DOIs
Publication statusPublished - May 1997

Fingerprint

Ketoprofen
Enantiomers
Carboxylic Acids
Labeling
Fluorescence
Derivatives
Acids
Amides
Anti-Inflammatory Agents
High Pressure Liquid Chromatography
High performance liquid chromatography
Temperature
Water
Chemical activation
Pharmaceutical Preparations
Wavelength
acetonitrile
triphenylphosphine
2,2'-dipyridyl disulfide

Keywords

  • 1-(5-Dimethylamino-1-naphthalenesulphonyl)-(S)-3-aminopyrrolidine (DNS-Apy)
  • Carboxylic acid enantiomers
  • Chiral derivatization reagent
  • Fluorescence detection
  • HPLC separation

ASJC Scopus subject areas

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

Cite this

1-(5-Dimethylamino-1-naphthalenesulphonyl)-(S)- 3-aminopyrrolidine (DNS-Apy) as a fluorescence chiral labelling reagent for carboxylic acid enantiomers. / Al-Kindy, Salma; Santa, Tomofumi; Fukushima, Takeshi; Homma, Hiroshi; Imai, Kazuhiro.

In: Biomedical Chromatography, Vol. 11, No. 3, 05.1997, p. 137-142.

Research output: Contribution to journalArticle

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