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Application of an unusual ninhydrin-based reaction for the indirect chiral resolution of D,L-penicillamine

By Salvatore Sotgia, Angelo Zinellu, Gérard Aimé Pinna, Luca Deiana and Ciriaco Carru

Abstract

An unusual reaction involving ninhydrin and aminothiols was exploited to set an indirect method for the chiral recognition of stereoisomers of penicillamine. Separation of diastereoisomers was achieved on a C18 column in isocratic mode by using a mixture of propionic acid (pH 3.0)/acetonitrile/water (10:10:80, v/v/v) as a mobile phase. Diastereoisomers were detected by a fluorescence detector in fairly short times (about 7 min) and with a good resolution. The lowest detectable amount of toxic isomer of penicillamine (l-enantiomer) in samples of the d-enantiomer, was around 0.01%. The method was also suitable for the indirect chiral recognition of other aminothiols such as cysteine and cysteinylglycine

Topics: BIO/14 Farmacologia, BIO/12 Biochimica clinica e biologia molecolare clinica
Publisher: Elsevier
Year: 2011
DOI identifier: 10.1016/j.talanta.2011.07.007
OAI identifier: oai:eprints.uniss.it:6386
Provided by: UnissResearch
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