A liquid chromatography-mass spectrometry study on the spirocyclization of ninhydrin with the aminothiols
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Date
2018-05-25Author
Sotgia, Salvatore
Zinellu, Angelo
Forteschi, Mauro
Paliogiannis, Panagiotis
Deiana, Giovanni A
Pinna, Gerard A
Carru, Ciriaco
Metadata
Show full item recordAbstract
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.
Description
© 2018 Elsevier BV. This manuscript version is made available under the CC-BY-NC-ND 4.0 license:
http://creativecommons.org/licenses/by-nc-nd/4.0/
This author accepted manuscript is made available following 24 month embargo from date of publication (May 2018) in accordance with the publisher’s archiving policy.