Determination of the enantiomeric purity of nucleoside analogs related to d4T and acyclovir, new potential antiviral agents, using liquid chromatography on cellulose chiral stationary phases. | LitMetric
Laboratoire de Chimie Analytique, Faculté des Sciences Pharmaceutiques et Biologiques, Université de Lille 2, France.
Published: October 2002
AI Article Synopsis
Article Abstract
We reported a method of determination of enantiomeric purity of the new potential antiviral agents by direct analytical HPLC. Those agents are nucleoside analogs, having one chiral center. They are synthesized as a single enantiomer (R or S) by an asymmetric pathway. The chiral stationary phases chosen are silica-based cellulose tris-3,5-dimethylphenylcarbamate (Chiralcel OD-H), or tris-methylbenzoate (Chiralcel OJ). Resolution was achieved using normal-phase chromatography with a mobile phase consisting of n-hexane-alcohol (ethanol or 2-propanol) in various percentages. Furthermore the effects of structural features on retention, selectivity and resolution, as well as on the elution order were thoroughly studied. Differences in the lipophilicity of the compounds were also examined.
Oxidized derivatives of cholesterol play an important role in the functioning of biomembranes. Unlike other biomolecules, which are physiologically active in only one enantiomeric form, some oxysterols exist endogenously as two stereoisomers that exhibit strictly different biological effects. In this paper, we focused our attention on 22-hydroxycholesterol (22-OH) epimers, 22()-OH and 22()-OH, and examined their properties in Langmuir monolayers spread at the air/water interface, using classical surface manometry complemented with Brewster angle microscopy (BAM) images of the film texture.
The 1,3-dithiolane ring has been recently rehabilitated as a chemical scaffold in drug design. However, for derivatives that are substituted in position 4, the introduction of a chiral center on the heterocycle demands the separation and characterization of the stereoisomers. We report the first chiral resolution and absolute configuration (AC) assignment for (1,4-dithiaspiro[4.
Improved methods for the synthesis of nicotine are of great importance due to the wide range of applications of synthetic nicotine, which is free from contamination with nitrosamines. Herein, we present a four-step chemical synthesis of ()-nicotine, involving the reduction in myosmine, enantiomeric separation of nornicotine, and subsequent methylation of the appropriate enantiomer of nornicotine obtained. The reduction in myosmine was investigated using both electrochemical and chemical approaches, achieving up to 90% yields of pure nornicotine.
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