Abstract
Chiral ligand-exchange chromatography (CLEC) first described in the late 1960s to early 1970s by Davankov and Rogozhin can be still considered as an elective choice for the direct enantioseparation of compounds endowed with chelating moieties. Among the numerous chelating species that have been evaluated as chiral selectors in ligand-exchange (LE) chromatography, a special role is played by a group of amino acids including proline, hydroxyproline, cysteine, phenylalanine, and penicillamine. More to the point, relevant chromatographic performances are also provided by amino alcohol-based chiral selectors, among which, those carrying a leucinol residue as the basic scaffold are worth to be mentioned.
Among the various enantiomer chromatographic separation techniques, CLEC has been exploited in all the main techniques including a chiral mobile phase (CMP), a covalently bound chiral stationary phase (B-CSP), and a coated chiral stationary phase (C-CSP). It is the objective of this chapter to describe selected CLEC applications dealing with the above three distinct approaches.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Marchelli R et al (2007) Enantioselective separation of amino acids and hydroxy acids by ligand exchange with copper(II) complexes in HPLC (chiral eluent) and in fast sensing systems. In: Subramanian G (ed) Chiral separation techniques, 3rd edn. Wiley, Weinheim, pp 301–331
Gübitz G, Schmid GM (2007) Chiral separation by ligand exchange. In: Subramanian G (ed) Chiral separation techniques, 3rd edn. Wiley, Weinheim, pp 155–179
Kurganov AA (2001) Chiral chromatographic separations based on ligand exchange. J Chromatogr A 906:51–71
Davankov VA, Kurganov AA, Ponomareva TM (1988) Enantioselectivity of complex formation in ligand-exchange chromatographic systems with chiral stationary and/or chiral mobile phases. J Chromatogr 452:309–316
Natalini B et al (2011) Mechanistic aspects and applications of chiral ligand-exchange chromatography. In: Grushka E, Grinberg N (eds) Advances in chromatography, vol 49. CRC Press, Boca Raton, pp 71–134
Davankov VA (1994) Chiral selectors with chelating properties in liquid chromatography: fundamental reflections and selective review of recent developments. J Chromatogr A 666:55–76
Schmid MG et al (2006) Fast chiral separation by ligand-exchange HPLC using a dynamically coated monolithic column. J Sep Sci 29:1470–1475
Gübitz G, Juffmann F, Jellenz W (1982) Direct separation of amino acid enantiomers by high performance ligand exchange chromatography on chemically bonded chiral phases. Chromatographia 16:103–106
Natalini B et al (2008) S-Trityl-(R)-cysteine, a powerful chiral selector for the analytical and preparative ligand-exchange chromatography of amino acids. J Sep Sci 31:696–704
Wan Q-H et al (1997) Chiral chromatography of amino acids on porous graphitic carbon coated with a series of N-substituted L-phenylalanine selectors. Effect of the anchor molecule on enantioselectivity. J Chromatogr A 765:187–200
Wernicke R (1985) Separation of underivatised amino acid enantiomers by mean of a chiral solvent-generated phase. J Chromatogr Sci 23:39–47
Natalini B, Sardella R, Pellicciari R (2005) O-Benzyl-(S)-serine, a new chiral selector for ligand-exchange chromatography of amino acids. Curr Anal Chem 1:85–92
Ôi N, Kitahara H, Aoki F (1995) Direct separation of carboxylic acid and amine enantiomers by high-performance liquid chromatography on reversed-phase silica gels coated with chiral copper(II) complexes. J Chromatogr A 707:380–383
Hyun MH, Ryoo J-J (1996) Optical resolution of racemic α-amino acids on a dynamic chiral stationary phase derived from (S)-leucinol by ligand exchange chromatography. J Liq Chromatogr Rel Technol 19:2635–2648
Hyun MH et al (2002) Preparation and application of a new ligand exchange chiral stationary phase for the liquid chromatographic resolution of α-amino acid enantiomers. J Chromatogr A 950:55–63
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer Science+Business Media, LLC
About this protocol
Cite this protocol
Natalini, B., Sardella, R., Ianni, F. (2013). Enantioseparations by High-Performance Liquid Chromatography Based on Chiral Ligand-Exchange. In: Scriba, G. (eds) Chiral Separations. Methods in Molecular Biology, vol 970. Humana Press, Totowa, NJ. https://doi.org/10.1007/978-1-62703-263-6_11
Download citation
DOI: https://doi.org/10.1007/978-1-62703-263-6_11
Published:
Publisher Name: Humana Press, Totowa, NJ
Print ISBN: 978-1-62703-262-9
Online ISBN: 978-1-62703-263-6
eBook Packages: Springer Protocols