Direct Resolution of Amino Acid Enantiomers by High Pressure Liquid Chromatography

Abstract

We have synthetized an optically active macromolecular chromatographic packing from cross-linked polyacrylamide grafted with an optically active ",-amino acid. This packing, in the form of small beads, slightly swells in water. Its granularity, porosityand rigidity are suitable for high pressure liquidchromatography. Such packings, complexed by a metallic ion, are efficient for the resolution of many underivatized racemic a-amino acids by elution with water. As an example,on one of these packings, containing Cu++ ions, enantiomers of valine, threonine, isoleucine, serine, phenylalanine, tyrosine, tryptophan, and asparagineare completely resolvedin less than one hour. ADVANCES IN THE CHROMATOGRAPHIC RESOLUTIONOF ENANTIOMERS

Characterization of substitution-inert cobalt(III) complex bonded-phase columns for liquid chromatography

“…We will refer to columns of length less than 2 cm as "minicolumns" to differentiate them from columns which are usually considered to be short columns, i.e., [2][3][4][5] cm columns.…”

“…Affinity chromatography is much more selective than other forms of chromatography. When "specific" affinity ligands, such as antibodies or enzyme inhibitors, are immobilized, only one solute should be adsorbed (4,5). When "general" affinity ligands, such as lectins or nucleotides, are immobilized, several solutes may be adsorbed (4,5).…”

“…One novel application of ligand exchange chromatography is the separation of enantiomers, particularly, dand Z-amino 0003-2700/83/0355-1390$01.50/0 © 1983 American Chemical Society acids (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16). In most cases, the separations are based on the in situ stereoselective formation of the chiral diastereomeric ternary metal complexes.…”

Chiral separation of α‐amino acids by ligand‐exchange capillary electrophoresis using N‐(2‐hydroxy‐octyl)‐L‐4‐hydroxyproline as a selector

“…LEC is a technique employed for compounds which coordinate with transition metal ions, giving complex species of different stability [2]. While Davankov [I] and Lefebvre [3] performed chiral separations of amino acids using polymer resins, which contained L-amino acid residues, Gubitz et al [4,51 developed chemically modified silica gel phases for this purpose. Subsequently, a great variety of papers dealing with chiral LEC have been published using either chiral stationary phases or chiral mobile phase additives [2].…”

Stereoselective effect on ternary complexation of copper ions with N,N′-dimethyltartramide and mandelic acid

“…The dependance of the thermodynamic stability of copper complexes with optically active ligands on the resolution of racemates was first reported about ten years ago during ligand exchange chromatography of racemates by Davankov and Rogozhin ( I , 2), mainly for a-amino acids (3)(4)(5). On the other hand, little work has appeared on the separation of a-hydroxyacids or diols enantiomers, probably because these compounds show a less uniform behaviour than the amino acids.…”