New Hydrophilic Derivatives of Lasalocid and Their Complexes with Selected Metal Cations

Abstract

Two new esters of lasalocid, that are more hydrophilic, with glucose (LasGlu) and xylitol (LasX), have been synthesized, and their complexation of monovalent cations has been studied by various spectrometric and spectroscopic methods, such as ESI mass spectrometry, 1H, 13C NMR and FT-IR. Analyses of the results confirmed the synthesis of new esters with good yields. In order to carry out further studies, it was necessary to purify them using “flash“ liquid chromatography. It was confirmed that the newly obtained molecules, as well as their complexes with lithium, sodium and potassium cations, were stabilized by a strong system of intramolecular hydrogen bonds. It was found that the hydroxyl groups of esters derived from xylitol and glucose were also involved in the complexation of cations. The results of the PM6 semiempirical calculations permitted determination of the heat of formation (HOF), and visualization of the structure of the new esters and their complexes with the cations studied. All computation results are in agreement with the spectroscopic data.