60251-91-4Relevant academic research and scientific papers
HPLC separation of 2-aryloxycarboxylic acid enantiomers on chiral stationary phases
Charushin, V. N.,Chulakov, E. N.,Krasnov, V. P.,Levit, G. L.,Sadretdinova, L. Sh.,Tumashov, A. A.,Vakarov, S. A.
, p. 900 - 907 (2021/06/07)
The possibility for separating enantiomers of a number of practically significant 2-aryloxycarboxylic acids was studied by normal- and reversed-phase HPLC on popular chiral stationary phases. The best separation parameters were achieved on the chiral phases with the polysaccharide base Chiralcel OD-H and Chiralpack AD under the normal-phase HPLC conditions. The (S)- and (R)-enantiomers of 2-(1-naphthyloxy)- and 2-(2-iodophenoxy)propionic acids with enantiomeric excess ee >99% were isolated using preparative chiral HPLC.
Enantioselective hydrolysis of some 2-aryloxyalkanoic acid methyl esters and isosteric analogues using a penicillin G acylase-based HPLC monolithic silica column
Massolini, Gabriella,Calleri, Enrica,Lavecchia, Antonio,Loiodice, Fulvio,Lubda, Dieter,Temporini, Caterina,Fracchiolla, Giuseppe,Tortorella, Paolo,Novellino, Ettore,Caccialanza, Gabriele
, p. 535 - 542 (2007/10/03)
A technique based on liquid chromatography has been developed to facilitate studies of enantioselectivity in penicillin G acylase (PGA)-catalyzed hydrolysis of some 2-aryloxyalkanoic acid methyl esters and isosteric analogues. PGA was covalently immobilized on an aminopropyl monolithic silica support to create an immobilized HPLC-enzyme reactor. Two sets of experimental data were drawn to calculate the enantioselectivity (E) of the kinetically controlled enantiomer-differentiating reaction, the degree of substrate conversion and the enantiomeric excess of the product. The developed enzymatic reactor was coupled through a switching valve to an achiral analytical column for separation and quantitation of the hydrolysis products. The enantiomeric excess was determined off-line on a PGA-chiral stationary phase. In this way, highly precise E values were determined. A computational study related to the hydrolysis of the considered racemic esters was also carried out in order to unambiguously clarify both the substrate specificity and the enantioselectivity displayed by PGA.
