Stereochemical recognition of enantiomeric and diastereomeric dipeptides by high-performance liquid chromatography on a chiral stationary phase based upon immobilized alpha-chymotrypsin.

A series of 24 enantiomeric and diastereomeric dipeptides were chromatographed on a chiral stationary phase (CSP) based upon immobilized alpha-chymotrypsin (ACHT). The ACHT-CSP was able to resolve stereochemically a number of the enantiomeric D,D- and L,L-dipeptides as well as the diastereomeric D,D-/L,L- and L,D-/D,L-dipeptides. The solutes were also chromatographed on a N-tosyl-L-phenylalanine chloromethyl ketone-deactivated form of the ACHT-CSP, where stereochemical separations were also achieved. The results of this study suggest that binding interactions between the dipeptides and the ACHT-CSP occur at the active site of the ACHT and at other hydrophobic sites on the ACHT molecule.