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 language | English |
|---|---|
| Pages (from-to) | 137-142 |
| Number of pages | 6 |
| Journal | Biomedical Chromatography |
| Volume | 11 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - May 1997 |
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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 journal › Article
}
TY - JOUR
T1 - 1-(5-Dimethylamino-1-naphthalenesulphonyl)-(S)- 3-aminopyrrolidine (DNS-Apy) as a fluorescence chiral labelling reagent for carboxylic acid enantiomers
AU - Al-Kindy, Salma
AU - Santa, Tomofumi
AU - Fukushima, Takeshi
AU - Homma, Hiroshi
AU - Imai, Kazuhiro
PY - 1997/5
Y1 - 1997/5
N2 - 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.
AB - 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.
KW - 1-(5-Dimethylamino-1-naphthalenesulphonyl)-(S)-3-aminopyrrolidine (DNS-Apy)
KW - Carboxylic acid enantiomers
KW - Chiral derivatization reagent
KW - Fluorescence detection
KW - HPLC separation
UR - http://www.scopus.com/inward/record.url?scp=0031011350&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0031011350&partnerID=8YFLogxK
U2 - 10.1002/(SICI)1099-0801(199705)11:3<137::AID-BMC648>3.0.CO;2-T
DO - 10.1002/(SICI)1099-0801(199705)11:3<137::AID-BMC648>3.0.CO;2-T
M3 - Article
VL - 11
SP - 137
EP - 142
JO - Biomedical Chromatography
JF - Biomedical Chromatography
SN - 0269-3879
IS - 3
ER -