A L-RNA aptamer chiral stationary phase for the resolution of target and related compounds.
In this paper, we report for the first time an aptamer-based chiral stationary phase (CSP) able to resolve racemates of both target and various related compounds. The enantiomers of tyrosine and analogues (11 enantiomeric pairs) were separated using an immobilized tyrosine-specific L-RNA aptamer as CSP and an aqueous buffer (8 mM Tris-HCl buffer, 25 mM NaCl, 5 mM MgCl2; pH 7.4) as mobile phase, at a column temperature of 10 degrees C. It appeared that the carboxylic and amino groups as well as the aromatic side chain of amino acid controlled the stereospecific recognition. Modifications on the polar groups were strongly detrimental for enantioselectivity while the replacement of the phenolic group by some bicyclic aromatic residues of different polarity, size or shape did not impair the enantioselective interaction. In addition, the effects of the mobile phase composition and column temperature upon the retention and stereoselective properties of the CSP were assessed. Finally, it was found that the immobilized RNA aptamer could be used under hydro-organic mobile phase conditions without alteration of the stationary phase stability.
Département de Pharmacochimie Moléculaire UMR 5063 CNRS, Institut de Chimie Moléculaire de Grenoble FR 2607, Université Joseph Fourier, UFR de Pharmacie de Grenoble, Avenue de Verdun, 38240 Meylan, France.
Corinne
C
Ravelet
Rym
R
Boulkedid
Anne
A
Ravel
Catherine
C
Grosset
Annick
A
Villet
Jennifer
J
Fize
Eric
E
Peyrin
D001483:Base Sequence; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation*; D009690:Nucleic Acid Conformation; D012313:RNA / Q000737:chemistry*; D013237:Stereoisomerism
D012313:RNA