Optical Resolution of Some Derivatives of D,L-Amino Acids by Chiral Liquid Chromatography

Enantioselective interaction of silica-immobilized bovine serum albumin (BSA) with some amino acid derivatives has been investigated by chiral HPLC. High enantiomeric separation factors (α > 5) were found for N-(o-carboxybenzoyl)-alanine (Ia) and N-phthalimidothreonine (II). Both enantiomers of Ia were less retained than those of the precursor N-phtalimido-alanine (I). The N-benzenesulfonyl derivatives of serine and alanine were both optically resolved at low pH (5.8) with moderate α-values (1.3 and 1.5 respectively).