High‐performance liquid chromatographic separation of penicillamine enantiomers labelled with N‐[4‐(6‐dimethylamino‐2‐benzofuranyl)phenyl]maleimide on a chiral stationary phase

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Abstract
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 (D1−, D2−, L1− and L2 DBPM), which could be separated on a Pirkle‐type chiral stationary phase using an eluent of 75% aqueous methanol solution containing 0.15 M CH3COONH4 and 0.05 M tetra‐n‐butylammonium bromide. Two of the peaks (D1− or L1‐DBPM), having a shorter retention time than the others, had almost the same retention times (25 min for D1‐DBPM and 25.7 min for L1‐DBPM). The retention times of the peaks eluted later were 28 min and 31.6 min for D2‐ and L2‐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.

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