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Original Articles

Mechanistic Studies of the Separation of an HIV Protease Inhibitor from Its Piperazine Diastereomer by Reversed Phase High Performance Liquid Chromatography

, , &
Pages 3343-3355 | Received 08 Jun 2003, Accepted 18 Jul 2003, Published online: 17 Aug 2006
 

Abstract

The HPLC separation and retention behavior of the piperazine diastereomers of an Human Immunodeficiency Virus (HIV) protease inhibitor on a commercially available C18 chromatographic phase is discussed. The pH and mobile phase composition have the greatest effect on the selectivity of this system. Evidence is presented that the selective interaction involves hydrogen bonding. As the mobile phase pH was varied, a reversal in the elution order corresponding to the change in the protonation state of the molecule is observed. It is proposed, that the selectivity is governed by coordination of the active piperazine amine as a proton donor or proton acceptor with the organic modifier, while interacting with the stationary phase. It is shown, that longer chain alcohols produce poorer selectivities than shorter chain alcohols. It is proposed, that this is because it is more difficult for the longer hydrophobic chains to form stable complexes with the solute through hydrogen bonding. The hydrogen bonding moiety of the solute may, thus, coordinate with water and not selectively interact with the stationary phase. The effects of stationary phase chemistry, ionic strength, and modifier strength are also described.

Acknowledgments

The authors wish to acknowledge Drs. A. Clausen, M. Trone, and F. Wang for helpful discussions.

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