Ninhydrin reacts with some aminothiols to form spiranes adducts whose optical and chromatographic properties have proved to be useful for chiral recognition. Liquid chromatography-mass spectrometry data along with spectroscopic analysis reveal that under certain conditions, in addition to the known single-spirane configuration, the spirothiazolidinic complexes can exist also as double- and mixed double-spiranes. The reaction was exploited to check the enantiomeric purity of two commercially available dosage form of D-penicillamine and to measure the aminothiol concentration in the urine sample from a subject under treatment with the drug. Separation of diastereoisomers was achieved on a C18 column in isocratic mode by using a mixture of an aqueous solution of formic acid (30 mmol/L)/acetonitrile (90:10, v/v) as a mobile phase. Diastereoisomers were detected by a fluorescence detector and mass spectrometer in short times and with a good resolution. Intra- and inter-assay reproducibility were under 4% with an average recovery of 98%. At a LOD of 0.01%, no evidence of the toxic distomer (L-enantiomer) was found in the biological sample and drugs.

A liquid chromatography-mass spectrometry study on the spirocyclization of ninhydrin with the aminothiols / Sotgia, Salvatore; Zinellu, Angelo; Forteschi, Mauro; Paliogiannis, Panagiotis; Deiana, Giovanni A.; Pinna, Gerard A.; Mangoni, Arduino A.; Carru, Ciriaco. - In: MICROCHEMICAL JOURNAL. - ISSN 0026-265X. - 141(2018), pp. 324-329. [10.1016/j.microc.2018.05.048]

A liquid chromatography-mass spectrometry study on the spirocyclization of ninhydrin with the aminothiols

Sotgia, Salvatore
;
Zinellu, Angelo;Paliogiannis, Panagiotis;Deiana, Giovanni A.;Pinna, Gerard A.;Carru, Ciriaco
2018

Abstract

Ninhydrin reacts with some aminothiols to form spiranes adducts whose optical and chromatographic properties have proved to be useful for chiral recognition. Liquid chromatography-mass spectrometry data along with spectroscopic analysis reveal that under certain conditions, in addition to the known single-spirane configuration, the spirothiazolidinic complexes can exist also as double- and mixed double-spiranes. The reaction was exploited to check the enantiomeric purity of two commercially available dosage form of D-penicillamine and to measure the aminothiol concentration in the urine sample from a subject under treatment with the drug. Separation of diastereoisomers was achieved on a C18 column in isocratic mode by using a mixture of an aqueous solution of formic acid (30 mmol/L)/acetonitrile (90:10, v/v) as a mobile phase. Diastereoisomers were detected by a fluorescence detector and mass spectrometer in short times and with a good resolution. Intra- and inter-assay reproducibility were under 4% with an average recovery of 98%. At a LOD of 0.01%, no evidence of the toxic distomer (L-enantiomer) was found in the biological sample and drugs.
A liquid chromatography-mass spectrometry study on the spirocyclization of ninhydrin with the aminothiols / Sotgia, Salvatore; Zinellu, Angelo; Forteschi, Mauro; Paliogiannis, Panagiotis; Deiana, Giovanni A.; Pinna, Gerard A.; Mangoni, Arduino A.; Carru, Ciriaco. - In: MICROCHEMICAL JOURNAL. - ISSN 0026-265X. - 141(2018), pp. 324-329. [10.1016/j.microc.2018.05.048]
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11388/209292
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