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High‐performance liquid chromatographic separation of penicillamine enantiomers labelled with N ‐[4‐(6‐dimethylamino‐2‐benzofuranyl)phenyl]maleimide on a chiral stationary phase
Author(s) -
Nakashima Kenichiro,
Ishimaru Tomoko,
Kuroda Naotaka,
Akiyama Shuzo
Publication year - 1995
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.1130090207
Subject(s) - maleimide , chemistry , enantiomer , chromatography , chiral stationary phase , penicillamine , phase (matter) , chromatographic separation , stationary phase , high performance liquid chromatography , stereochemistry , organic chemistry
Penicillamine enatiomers derivatized with N ‐[4‐(6‐dimethylamino‐2‐benzofuranyl)phenyl]maleimide (DBPM) were separated and determined by high‐performance liquid chromatography. A fluorogenic reagent, DBPM easily reacted with D ‐ or L ‐penicillamine to give each two kinds of strong fluorescent derivatives (D 1− , D 2− , L 1− and L 2 DBPM), which could be separated on a Pirkle‐type chiral stationary phase using an eluent of 75% aqueous methanol solution containing 0.15 M CH 3 COONH 4 and 0.05 M tetra‐ n ‐butylammonium bromide. Two of the peaks (D 1− or L 1 ‐DBPM), having a shorter retention time than the others, had almost the same retention times (25 min for D 1 ‐DBPM and 25.7 min for L 1 ‐DBPM). The retention times of the peaks eluted later were 28 min and 31.6 min for D 2 ‐ and L 2 ‐DBPM respectively. Linear calibration curves over the range of 2–50 pmol per injection were obtained for D ‐and L ‐penicillamines with a detection limit of 290 and 350 fmol at respectively at a signal‐to‐noise ratio of 3. Using the proposed method, the absence of contamination of L ‐penicillamine in a commercially available D ‐penicillamine preparation (capsule) was confirmed.