title: 1-(5-Dimethylamino-1-naphthalenesulphonyl)-(S)-3-aminopyrrolidine (DNS-Apy) as a fluorescence chiral labelling reagent for carboxylic acid enantiomers.
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.
authors.affiliation: Faculty of Pharmaceutical Sciences, University of Tokyo, Japan.
authors.forename: S
authors.initials: S
authors.lastname: al-Kindy
authors.forename: T
authors.initials: T
authors.lastname: Santa
authors.forename: T
authors.initials: T
authors.lastname: Fukushima
authors.forename: H
authors.initials: H
authors.lastname: Homma
authors.forename: K
authors.initials: K
authors.lastname: Imai
mesh_terms: D001578:Benzopyrans / Q000737:chemistry; D002264:Carboxylic Acids / Q000032:analysis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D003619:Dansyl Compounds / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D007052:Ibuprofen / Q000737:chemistry; D007660:Ketoprofen / Q000737:chemistry; D010666:Phenylpropionates / Q000737:chemistry*; D011422:Propionates / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism
chemical_list: C108054:1-(5-dimethylamino-1-naphthalenesulfonyl)-3-aminopyrrolidine; D001578:Benzopyrans; D002264:Carboxylic Acids; D003619:Dansyl Compounds; D005456:Fluorescent Dyes; D010666:Phenylpropionates; D011422:Propionates; D011759:Pyrrolidines; C043940:pyranoprofen; D007660:Ketoprofen; C011377:tropic acid; C013025:hydratropic acid; D007052:Ibuprofen