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Indirect resolution of enantiomers of penicillamine by TLC and HPLC using Marfey's reagent and its variants
Author(s) -
Bhushan R.,
Brückner H.,
Kumar Virender
Publication year - 2007
Publication title -
biomedical chromatography
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.4
H-Index - 65
eISSN - 1099-0801
pISSN - 0269-3879
DOI - 10.1002/bmc.854
Subject(s) - chemistry , chromatography , penicillamine , enantiomer , reagent , detection limit , triethylamine , acetonitrile , trifluoroacetic acid , high performance liquid chromatography , derivatization , elution , repeatability , diastereomer , stereochemistry , organic chemistry
TLC and HPLC methods were developed for indirect chiral separation of penicillamine (3,3‐dimethylcysteine) enantiomers after derivatization with Marfey's reagent (FDNP‐Ala‐NH 2 ) and two of its structural variants, FDNP‐Phe‐NH 2 and FDNP‐Val‐NH 2 . The binary mobile phase of phenol–water (3:1 v/v) and solvent combinations of acetonitrile and triethylamine phosphate buffer were found to give the best separation in normal and reversed‐phase TLC, respectively. The diastereomers were also resolved on a reversed‐phase C18 HPLC column with gradient elution of acetonitrile and 0.01 m trifluoroacetic acid. The results due to these three reagents were compared. The method was successful for checking the enantiomeric impurity of l ‐penicillamine in d‐ penicillamine and to check the enantiomeric purity of pharmaceutical formulations of d‐ penicillamine. The method was validated for linearity, repeatability, limit of detection and limit of quantification. Copyright © 2007 John Wiley & Sons, Ltd.