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Enantioselective influence of cyclodextrins on cleavage of chiralic esters
Author(s) -
Beyrich Thorsten,
Jira Thomas,
Beyer Christine
Publication year - 1995
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530070711
Subject(s) - chemistry , enantiomer , cleavage (geology) , enantioselective synthesis , hydrolysis , cyclodextrin , phenylacetic acid , high performance liquid chromatography , stereochemistry , chromatography , chiral column chromatography , reactivity (psychology) , organic chemistry , catalysis , medicine , alternative medicine , geotechnical engineering , pathology , fracture (geology) , engineering
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.