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

Sotgia, Salvatore and Zinellu, Angelo and Pinna, Gérard Aimé and Deiana, Luca and Carru, Ciriaco (2011) Application of an unusual ninhydrin-based reaction for the indirect chiral resolution of D,L-penicillamine. Talanta, Vol. 85 (4), p. 1783-1785. ISSN 0039-9140. Article.

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DOI: 10.1016/j.talanta.2011.07.007

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.

Item Type:Article
ID Code:6386
Status:Published
Refereed:Yes
Uncontrolled Keywords:Spirothiazolidine, ninhydrin, aminothiols, chiral derivatizing reagent, diastereoisomers
Subjects:Area 05 - Scienze biologiche > BIO/14 Farmacologia
Area 05 - Scienze biologiche > BIO/12 Biochimica clinica e biologia molecolare clinica
Divisions:001 Università di Sassari > 01 Dipartimenti > Scienze biomediche
002 Altri enti e centri di ricerca del Nord Sardegna > Porto Conte Ricerche, Alghero
001 Università di Sassari > 01 Dipartimenti > Farmaco, chimico, tossicologico
Publisher:Elsevier
ISSN:0039-9140
Copyright Holders:© 2011 Elsevier
Deposited On:23 Aug 2011 14:13

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