| Abstract: | 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 β-cyclodextrin (CD), hydroxyethyl- and hydroxypropyl-β-CD, as well as methyl-β-CD is studied photometrically and by means of HPLC (Chiralcel-OD-R-column). Both β-CD and hydroxyalkylated-β-CD catalyze (?)-(R)-enantiomers to a larger extent than (+)-(S)-enantiomers, resulting in an enrichment of the latter. Methyl-β-CD stabilizes the ester trifold, thus abolishing chiral discrimination. © 1995 Wiley-Liss, Inc. |
