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

作者：Sotgia Salvatore^*; Zinellu Angelo; Forteschi Mauro; Paliogiannis Panagiotis; Deiana Giovanni A; Pinna Gerard A; Mangoni Arduino A; Carru Ciriaco

来源：Microchemical Journal, 2018, 141: 324-329.

DOI：10.1016/j.microc.2018.05.048

• Spiranes
• Spirothiazolidine
• Chiral
• Diastereoisomers

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.

• 出版日期2018-9