Chiral liquid chromatography contribution to the determination of the absolute configuration of enantiomers.
The review covers examples in which chiral HPLC, as a source of pure enantiomers, has been combined with classical methods (X-ray, vibrational circular dichroism (VCD), enzymatic resolutions, nuclear magnetic resonance (NMR) techniques, optical rotation, circular dichroism (CD)) for the on- or off-line determination of absolute configuration of enantiomers. Furthermore, it is outlined that chiral HPLC, which associates enantioseparation process and classical purification process, opens new perspectives in the classical determination of absolute configuration by chemical correlation or chemical interconversion methods. The review also contains a discussion about the various approaches to predict the absolute configuration from the retention behavior of the enantiomers on chiral stationary phases (CSPs). Some examples illustrate the advantages and limitations of molecular modeling methods and the use of chiral recognition models. The assumptions underlying some of these methods are critically analyzed and some possible emerging new strategies are outlined.
Roussel
Christian
C
Faculté des Sciences St. Jêrôme, UMR Chirotechnologies: Catalyse et Biocatalyse, Université Aix-Marseille III, Avenue Escadrille Normandie Niemen, F-13397 Marseille Cedex 20, France. christian.roussel@univ.u-3mrs.fr
Del Rio
Alberto
A
Pierrot-Sanders
Johanna
J
Piras
Patrick
P
Vanthuyne
Nicolas
N
D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D002942:Circular Dichroism; D004798:Enzymes; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D009904:Optical Rotation; D013237:Stereoisomerism; D013816:Thermodynamics; D014732:Vibration; D014965:X-Rays
D004798:Enzymes