Assessing the reactivity of optical antipodes is of central importance
in drug research. Using the model of 2-methoxy-2-phenylacetic acid-4-
nitrophenylester (MPE), the rate of hydrolysis in the presence of beta
-cyclodextrin (CD), hydroxyethyl- and hydroxypropyl-beta-CD, as well a
s methyl-beta-CD is studied photometrically and by means of HPLC (Chir
alcel-OD-R-column). Both beta-CD and hydroxyalkylated-beta-CD catalyze
(-)-(R)-enantiomers to a larger extent than (+)-(S)-enantiomers, resu
lting in an enrichment of the latter. Methyl-beta-CD stabilizes the es
ter trifold, thus abolishing chiral discrimination. (C) 1995 Wiley-Lis
s, Inc.