Chiral liquid chromatography: past and present

Abstract

Around 1812, the French physicist Biot discovered the existence of optical activity in crystals of α-quartz(O’Loane, 1980). Credit for the first resolution of enantiomers from a racemate goes to Louis Pasteur who, in 1848, separated manually the non-identical crystals of the enantiomers of sodium ammonium tartrate (Pasteur, 1848). In 1874, Le Bel and Van’t Hoff independently proposed the ‘asymmetric carbon atom’ to account for the chirality of organic compounds. Le Bel (1874) favoured a square pyramidal arrangement of substituents around an apical carbon atom whereas Van’t Hoff (1874) correctly postulated a tetrahedral arrangement around a central carbon atom. Not surprisingly, early attempts to obtain resolution of racemates utilized readily-available, naturally-occurring chiral materials such as wool, silk, quartz and polysaccharides such as starch or cellulose. At the turn of the century, Wilstatter (1904) postulated that it should be possible to resolve racemic dyes in solution by enantioselective adsorption onto wool.