title: Liquid chromatographic resolution of amino acid esters of acyclovir including racemic valacyclovir on crown ether-based chiral stationary phases.
abstract: Valacyclovir, a potential prodrug for the treatment of patients with herpes simplex and herpes zoster, and its analogs were resolved on two chiral stationary phases (CSPs) based on (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6 covalently bonded to silica gel. In order to find out an appropriate mobile phase condition, various mobile phases consisting of various organic modifiers in water containing various acidic modifiers were applied to the resolution of valacyclovir and its analogs. When 30% acetonitrile in water containing any of 0.05 M, 0.10 M, or 0.15 M perchloric acid was used as a mobile phase, valacyclovir and its analogs were resolved quite well on the two CSPs with the separation factors (α) in the range of 2.49 ~ 6.35 and resolutions (RS ) in the range of 2.95 ~ 12.21. Between the two CSPs, the CSP containing residual silanol protecting n-octyl groups on the silica surface was found to be better than the CSP containing residual silanol groups.
authors: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan, Republic of Korea.
authors: Seong Ae
authors: SA
authors: Ahn
authors: Myung Ho
authors: MH
authors: Hyun
mesh_terms: D000212:Acyclovir / Q000031:analogs & derivatives* / Q000737:chemistry*; D000998:Antiviral Agents / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D004952:Esters / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D013237:Stereoisomerism; D000077483:Valacyclovir; D014633:Valine / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000998:Antiviral Agents; D004952:Esters; D014633:Valine; D000077483:Valacyclovir; D000212:Acyclovir
keywords: chiral stationary phase; enantiomer separation; liquid chromatography; valacyclovir