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Direct enantiomeric TLC resolution of dl ‐penicillamine using ( R )‐mandelic acid and l‐ tartaric acid as chiral impregnating reagents and as chiral mobile phase additive
Author(s) -
Bhushan Ravi,
Agarwal Charu
Publication year - 2008
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.1052
Subject(s) - chemistry , mandelic acid , tartaric acid , enantiomer , reagent , chiral resolution , acetic acid , methanol , acetonitrile , solvent , chromatography , enantiomeric excess , organic chemistry , enantioselective synthesis , catalysis , citric acid
dl ‐Penicillamine has been resolved into its enantiomers by normal‐phase TLC using l ‐tartaric acid as chiral impregnating reagent as well as chiral mobile phase additive, while ( R )‐mandelic acid has been found to be successful as a chiral impregnating reagent. The solvent system acetonitrile–methanol–water (5:1:1, v/v) was found to be successful when l ‐tartaric acid was used as impregnating agent while the solvent combination acetonitrile–methanol–(0.5% l ‐tartaric acid in water, pH 5)–glacial acetic acid (7:1:1.1:0.7, v/v) was successful as mobile phase as it contained l ‐tartaric acid as the chiral additive. ( R )‐mandelic acid was successful as chiral impregnating reagent with ethyl acetate–methanol–water (3:1:1, v/v), as the mobile phase. The effects of concentration of chiral selectors, temperature and pH were examined on enantiomeric resolution. The spots were detected with iodine vapors and the detection limits were found to be 0.12 µg for each enantiomer of penicillamine with l ‐tartaric acid, under both the conditions, and 0.11 µg with ( R )‐mandelic acid. Copyright © 2008 John Wiley & Sons, Ltd.