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

Biomedical Chromatography : BMC
S al-KindyK Imai

Abstract

1-(5-Dimethylamino-1-naphthalenesulphonyl)-(S)-3-aminopyrrolidi ne (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.

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Citations

Sep 6, 2008·Journal of Fluorescence·Salma M Z Al-KindyAvin Pillay
Nov 5, 2003·Biomedical Chromatography : BMC·Ramesh MullangiNuggehally R Srinivas
Jun 18, 2009·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·A G Hutton
May 29, 2016·Psychonomic Bulletin & Review·Eun-Kyung Lee, Jesse Snedeker
Jul 16, 2014·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·Z J Wang
Jul 16, 2014·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·U Piomelli
Jul 16, 2014·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·Sanjiva K Lele, Joseph W Nichols
Jul 16, 2014·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·Johan Larsson, Qiqi Wang

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