Vancomycin forms a stable complex with CU2+ in neutral aqueous solutio
ns. The enantioselectivity of native vancomycin was compared to that o
f the copper-vancomycin complex using capillary electrophoresis (CE).
There were significant differences in their enantioselectivities. This
can be attributed to the fact that copper ion coordinates with some o
f the same functional groups in vancomycin that are essential for chir
al recognition and enantioresolution. An amine moiety that provides on
e of the more important enantioselective interactions was identified.
This chiral interaction site was illustrated using a color-coded, spac
e-filling model of the X-ray crystal structure of the copper-vancomyci
n complex. Successful enantioselective interactions at lower pHs were
attributed to the partial dissociation of the copper-vancomycin comple
x. (C) 1997 Wiley-Liss, Inc.