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Experimental and Model Investigation of the Oscillatory Transenantiomerization of L-�-Phenylalanine

By Mieczysław Sajewicz, Monika Gontarska, Łukasz Wojtal, Dorota Kronenbach, Irving R. Epstein and Teresa Kowalska


Abstract: In an earlier study, we obtained experimental evidence of the oscillatory transenantiomerization of selected profen drugs (e.g., S-(+)ibuprofen, S-(+)-naproxen, and S-(+) and R-(−)-flurbiprofen) dissolved in aqueous, aqueous-organic, and purely organic liquid media. This process was apparently catalyzed by basic or amphiprotic environments and involved ketoenol tautomerism, and the self-organization of molecules in the solution via association of the carboxylic functional group of profens through hydrogen bonding to form mixed H-bonded associates with the remaining constituents of the solution. A model of the oscillatory transenantiomerization of profens was also developed by adapting an earlier oscillatory model, the Templator. Our new model comprises two linked Templators. The essence of the Templator model adapted to the oscillatory transenantiomerization of profens is the assumption that the H-bonded profen homodimer acts as a template, able to generate new dimers having the same steric configuration as their respective monomeric units. As profens belong to the class of 2-arylpropionic acids (2-APAs), we concluded that the phenomenon of oscillatory transenantiomerization may occur in other 2-APAs as well, among them those amino acids whose molecular structure can formally be derived from propionic acid. Thus, in this study, we Address correspondence to Teresa Kowalska, Institute of Chemistry

Year: 2013
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