RETENTION AND ENANTIOSELECTIVITY OF 2-ARYLPROPIONIC ACID-DERIVATIVES ON AN AVIDIN-BONDED SILICA COLUMN INFLUENCE OF BASE MATERIALS, SPACER TYPE AND PROTEIN MODIFICATION

The influences of pore sizes of base materials, spacer type and protei n modification on the chiral resolution of 2-arylpropionic acid deriva tives on avidin (AVD)-bonded silica materials were investigated. With regard to the pore sizes of the base silica materials, 120-Angstrom A materials gave higher enantioselectivity and resolution than 300-Angst rom A materials. With regard to spacer type, aminopropyl (AP)-silica g els activated by N,N'-disuccinimidyl carbonate (DSC) and N,N'-disuccin imidyl suberate (DSS) and glycerylpropyl (GP)-silica gels activated by 1,1'-carbonyldiimidazole (CDI) were compared. The AP-silica gels acti vated by DSC gave the highest protein coverage and resolution. Modifie d AVD-bonded materials were prepared by reaction with glutaraldehyde, glyceraldehyde and benzaldehyde. The retentive and enantioselective pr operties of 2-arylpropionic acid derivatives on these modified AVD col umns were compared with those on an unmodified AVD column. The retenti ons of 2-arylpropionic acid derivatives on the modified AVD columns we re shorter than those on the unmodified AVD column, whereas the modifi ed AVD columns gave lower or approximately equal enantioselectivity co mpared with the unmodified AVD column. These results may be attributed to a decrease in the number of ion-exchange sites for retention and c hiral recognition, and/or changes in protein conformation as a result of modification.