199679-82-8Relevant academic research and scientific papers
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 (2003)
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.
Isosteres of chiral clofibric acid analogs: Synthesis, resolution, absolute configuration and HPLC detection of the optical purity
Ferorelli,Loiodice,Tortorella,Amoroso,Bettoni,Conte- Camerino,De Luca
, p. 367 - 374 (2007/10/03)
Both racemic and enantiomeric forms of some isosteres of chiral clofibric acid analogs have been synthesized. Also, the absolute configuration has been established by chemical correlation and the optical purity determined by a simple HPLC procedure. Moreover, these studies show that the isosteric substitution of the ether oxygen atom of α-aryloxy- alkanoic acids with sulfur, amino and methylene groups lead to compounds in which both biological activity and stereoselectivity regarding chloride channel are highly reduced.
