HPLC Profile of Captopril Disulfide That Undergoes Reversible cis-trans Conversion among Three Isomers

NISHIKAWA Takashi, ABE Reiko, SUDO Yumiko, YAMADA Asako, TAHARA Kayoko

doi:10.2116/analsci.20.1395

HPLC Profile of Captopril Disulfide That Undergoes Reversible cis-trans Conversion among Three Isomers

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NISHIKAWA Takashi

Kyoritsu University of Pharmacy, Department of Medico-chemical Analysis
ABE Reiko

Kyoritsu University of Pharmacy, Department of Medico-chemical Analysis
SUDO Yumiko

Kyoritsu University of Pharmacy, Department of Medico-chemical Analysis
YAMADA Asako

Kyoritsu University of Pharmacy, Department of Medico-chemical Analysis
TAHARA Kayoko

Kyoritsu University of Pharmacy, Department of Medico-chemical Analysis

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Peculiarly shaped chromatograms of some compounds that consist of two reversible isomers have been reported. Those of a compound that consists of three reversible isomers are described here. Because disulfide of captopril has two cis-trans convertible bonds, it exists in three forms of cis-cis, cis-trans and trans-trans isomers. The disulfide has produced various HPLC-UV profiles under various conditions, such as three split peaks, three peaks with bridging plateaus and one broad peak. The effect of the column temperature and the eluent flow rate on the profile was investigated and explained by interconversion among three isomers. A profile analysis could provide some kinetic constants of this reaction.