1-(5-Dimethylamino-1-naphthalenesulphonyl)-(S)-3-aminopyrrolidine (DNS-Apy) as a Fluorescence Chiral Labelling Reagent for Carboxylic Acid Enantiomers
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...
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Published in | Biomedical chromatography Vol. 11; no. 3; pp. 137 - 142 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
Chichester, UK
John Wiley & Sons, Ltd
01.05.1997
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Subjects | |
Online Access | Get full text |
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Summary: | 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. © 1997 John Wiley & Sons, Ltd. |
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Bibliography: | Matsumae International Foundation ark:/67375/WNG-KPHH44LC-L istex:532421E4E55A3CC408610D314B29D9B1AE611506 ArticleID:BMC648 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0269-3879 1099-0801 |
DOI: | 10.1002/(SICI)1099-0801(199705)11:3<137::AID-BMC648>3.0.CO;2-T |