ISSN:
0899-0042
Keywords:
β-cyclodextrin
;
β-cyclodextrin derivatives
;
methyl-β-cyclodextrin
;
hydrolysis
;
2-methoxy-2-phenylacetic acid-4-nitrophenylester
;
methoxy mandelic acid esters
;
chirality
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chir.530070711
Permalink