title: Application of an unusual ninhydrin-based reaction for the indirect chiral resolution of D,L-penicillamine.
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.
authors.affiliation: Department of Biomedical Sciences, Chair of Clinical Biochemistry, University of Sassari, Viale San Pietro 43/B, I-07100 Sassari, Italy. salvatore.sotgia@gmail.com
authors.forename: Salvatore
authors.initials: S
authors.lastname: Sotgia
authors.forename: Angelo
authors.initials: A
authors.lastname: Zinellu
authors.forename: Gerard Aime
authors.initials: GA
authors.lastname: Pinna
authors.forename: Luca
authors.initials: L
authors.lastname: Deiana
authors.forename: Ciriaco
authors.initials: C
authors.lastname: Carru
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D056148:Chromatography, Reverse-Phase / Q000379:methods*; D003545:Cysteine / Q000737:chemistry; D009555:Ninhydrin / Q000737:chemistry*; D010396:Penicillamine / Q000737:chemistry* / Q000302:isolation & purification*; D013237:Stereoisomerism
chemical_list: D010396:Penicillamine; D009555:Ninhydrin; D003545:Cysteine