Abstract
Target-specific chiral selectors, which are characterized by a predictable elution order depending on the target enantiomer employed for the selection of the chiral selector, have recently received much attention in the enantioselective analysis field. In this context, bioaffinity-based molecular recognition tools such as nucleic acid aptamers have notably demonstrated very attractive features for the chiral discrimination of active molecules. In this chapter, the enantioselective properties of aptamer chiral selectors and the major factors that control and modulate the liquid chromatography and capillary electrophoresis enantiomer separation are addressed.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Francotte ER (2001) Enantioselective chromatography as a powerful alternative for the preparation of drug enantiomers. J Chromatogr A 906:379–397
Ansell RJ (2005) Molecularly imprinted polymers for the enantioseparation of chiral drugs. Adv Drug Deliv Rev 57:1809–1835
Nilsson J, Spégel P, Nilsson S (2004) Molecularly imprinted polymer formats for capillary electrochromatography. J Chromatogr B 804:3–12
Hofstetter H, Hofstetter O (2005) Antibodies as tailor-made chiral selectors for detection and separation of stereoisomers. Trends Anal Chem 10:869–879
Ellington AD, Szostak JW (1990) In vitro selection of RNA molecules that bind specific ligands. Nature 346:818–822
Jayasena SD (1999) Aptamers: an emerging class of molecules that rival antibodies in diagnostics. Clin Chem 45:1628–1650
Tombelli S, Mascini M (2009) Aptamers as molecular tools for bioanalytical methods. Curr Opin Mol Ther 11:179–188
Müller M, Weigand JE, Weichenrieder O et al (2006) Thermodynamic characterization of an engineered tetracycline-binding riboswitch. Nucleic Acids Res 34:2607–2617
Hermann T, Patel DJ (2001) Adaptive recognition by nucleic acid aptamers. Science 287:820–825
Latham MP, Zimmermann GR, Pardi A (2009) NMR chemical exchange as a probe for ligand-binding kinetics in a theophylline-binding RNA aptamer. J Am Chem Soc 131:5052–5053
Schneider C, Sühnel J (1999) A molecular dynamics simulation of the flavin mononucleotide-RNA aptamer complex. Biopolymers 50:287–302
Bishop GR, Ren J, Polander BC et al (2007) Energetic basis of molecular recognition in a DNA aptamer. Biophys Chem 126:165–175
Lin PH, Yen SL, Lin MS et al (2008) Microcalorimetrics studies of the thermodynamics and binding mechanism between l-tyrosinamide and aptamer. J Phys Chem B 112:6665–6673
Jenison RD, Gill SC, Pardi A et al (1994) High-resolution molecular discrimination by RNA. Science 263:1425–1429
Klussmann S, Nolte A, Bald R et al (1996) Mirror-image RNA that binds d-adenosine. Nat Biotechnol 14:1112–1115
Shoji A, Kuwahara M, Ozaki H et al (2007) Modified DNA aptamer that binds the (R)-isomer of a thalidomide derivative with high enantioselectivity. J Am Chem Soc 129:1456–1464
Geiger A, Burgstaller P, von der Eltz H et al (1996) RNA aptamers that bind l-arginine with sub-micromolar dissociation constants and high enantioselectivity. Nucleic Acids Res 24:1029–1036
Majerfeld I, Puthenvedu D, Yarus M (2005) RNA affinity for molecular l-histidine; genetic code origins. J Mol Evol 61:226–235
Majerfeld I, Yarus M (2005) A diminutive and specific RNA binding site for l-tryptophan. Nucleic Acids Res 33:5482–5493
Williams KP, Liu XH, Schumacher TN et al (1997) Bioactive and nuclease-resistant l-DNA ligand of vasopressin. Proc Natl Acad Sci USA 94:11285–11290
Michaud E, Jourdan EA, Villet A et al (2003) A DNA aptamer as a new target-specific chiral selector for HPLC. J Am Chem Soc 125:8672–8679
Michaud M, Jourdan E, Ravelet C et al (2004) Immobilized DNA aptamers as target-specific chiral stationary phases for resolution of nucleoside and amino acid derivative enantiomers. Anal Chem 76:1015–1020
Ruta J, Ravelet C, Désiré J et al (2008) Covalently bonded DNA aptamer chiral stationary phase for the chromatographic resolution of adenosine. Anal Bioanal Chem 390:1051–1057
Brumbt A, Ravelet C, Grosset C et al (2005) Chiral stationary phase based on a biostable l-RNA aptamer. Anal Chem 77:1993–1998
Ruta J, Grosset C, Ravelet C et al (2007) Chiral resolution of histidine using an anti-d-histidine l-RNA aptamer microbore column. J Chromatogr B 845:186–190
Ravelet C, Boulkedid R, Ravel A et al (2005) A l-RNA aptamer chiral stationary phase for resolution of target and related compounds. J Chromatogr A 1076:62–70
Ruta J, Ravelet C, Grosset C et al (2006) Enantiomeric separation using an l-RNA aptamer as chiral additive in partial-filling capillary electrophoresis. Anal Chem 78:3032–3039
Ruta J, Perrier S, Ravelet C et al (2009) Aptamer-modified micellar electrokinetic chromatography for the enantioseparation of nucleotides. Anal Chem 81:1169–1176
Brion P, Westhof E (1997) Hierarchy and dynamics of RNA folding. Annu Rev Biophys Biomol Struct 26:113–137
Draper DE, Grilley D, Soto AM (2005) Ions and RNA folding. Annu Rev Biophys Biomol Struct 34:221–243
Tittelbach V, Gilpin RK (1995) Species dependency of the liquid chromatographic properties of silica-immobilized serum albumins. Anal Chem 67:44–47
Hofstetter O, Lindstrom H, Hofstetter H (2004) Effect of the mobile phase on antibody-based enantiomer separations of amino acids in high-performance liquid chromatography. J Chromatogr A 1049:85–95
Ruta J, Ravelet C, Baussanne I et al (2007) Aptamer-based enantioselective competitive binding assay for the trace enantiomer detection. Anal Chem 79:4716–4719
Ruta J, Ravelet C, Baussane I et al (2008) Competitive affinity capillary electrophoresis assay based on a “hybrid” pre-incubation/on-capillary mixing format using an enantioselective aptamer as affinity ligand. J Sep Sci 31:2239–2243
Ruta J, Perrier S, Ravelet C et al (2009) Noncompetitive fluorescence polarization aptamer-based assay for small molecule detection. Anal Chem 81:7468–7473
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2010 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Peyrin, E. (2010). Enantioselective Properties of Nucleic Acid Aptamer Molecular Recognition Elements. In: Berthod, A. (eds) Chiral Recognition in Separation Methods. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-12445-7_10
Download citation
DOI: https://doi.org/10.1007/978-3-642-12445-7_10
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-12444-0
Online ISBN: 978-3-642-12445-7
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)