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

Salvatore Sotgia, Angelo Zinellu, Mauro Forteschi, Panagiotis Paliogiannis, Giovanni A Deiana, Gerard A Pinna, Arduino A Mangoni, Ciriaco Carru

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)324-329
Number of pages6
JournalMICROCHEMICAL JOURNAL
Volume141
DOIs
Publication statusPublished - Sep 2018

Keywords

  • Chiral
  • Diastereoisomers
  • Spiranes
  • Spirothiazolidine

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    Sotgia, S., Zinellu, A., Forteschi, M., Paliogiannis, P., Deiana, G. A., Pinna, G. A., Mangoni, A. A., & Carru, C. (2018). A liquid chromatography-mass spectrometry study on the spirocyclization of ninhydrin with the aminothiols. MICROCHEMICAL JOURNAL, 141, 324-329. https://doi.org/10.1016/j.microc.2018.05.048