Diastereomeric resolution of nucleoside analogues, new potential antiviral agents, using high-performance liquid chromatography on polysaccharide-type chiral stationary phases.
This paper describes the separation of the four sets of stereoisomers of nucleoside analogs, new potential antiviral agents by direct analytical HPLC methods using derivatized cellulose and amylose chiral stationary phases. The resolution was made using normal-phase methodology with a mobile phase consisting of n-hexane-alcohol (ethanol or 2-propanol) in various percentages, and a silica-based cellulose tris-3,5-dimethylphenylcarbamate (Chiralcel OD-H), or tris-methylbenzoate (Chiralcel OJ) and a silica-based amylose tris-3,5-dimethylphenylcarbamate (Chiralpak AD) or tris-(S)-1-phenylethylcarbamate (Chiralpak AS). The effects of structural features on the extent of discrimination between the stereoisomers were examined through the retention, the selectivity and the resolution factors as well as the elution order. Baseline separation (Rs>1.5) was easily obtained in many cases. The resolution results were complementary between the different columns.
Lipka-Belloli
Emmanuelle
E
Laboratoire de Chimie Analytique, Faculté des Sciences Pharmaceutiques, Université de Lille, France.
Len
Christophe
C
Mackenzie
Grahame
G
Ronco
Gino
G
Bonte
Jean-Paul
JP
Vaccher
Claude
C
D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D009705:Nucleosides / Q000302:isolation & purification*; D011134:Polysaccharides / Q000737:chemistry*; D013237:Stereoisomerism
D009705:Nucleosides; D011134:Polysaccharides