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1 2009

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On the spontaneous condensation of selected hydroxy acids

Sajewicz M., Matlengiewicz M., Kronenbach D., Gontarska M., Kowalska T.

Acta Chromatographica

2009

Vol. 21, no. 2

259--271

In a previous study we provided thin-layer chromatographic, polarimetric, and other experimental evidence that phenylglycine can undergo easy spontaneous peptidization in abiotic aqueous media. From our unpublished results it is apparent that this behaviour is also characteristic of some other amino acids (e.g., alanine and phenylalanine). It seems highly probable that this abiotic peptidization of amino acids dissolved in aqueous media is directly linked to their ability to undergo spontaneous oscillatory chiral conversion. In our earlier research it was also shown that spontaneous oscillatory chiral conversion was characteristic not only of amino acids but also of several other classes of carboxylic acid, including profen drugs and hydroxy acids. We therefore decided to check whether selected chiral hydroxy acids — lactic acid and mandelic acid — previously recognized for their ability to undergo spontaneous oscillatory chiral conversion, could also furnish the respective polyacids. Condensation of hydroxy acids can be viewed as a reaction fully analogous with peptidization of amino acids and, hence, it seemed to us highly probable that it also can be triggered by oscillatory chiral conversion. In our study, we used thin-layer chromatography and 13 C NMR spectroscopy to check whether formation of polylactic acid and polymandelic acid occurred in stored solutions of lactic and mandelic acids. By means of polarimetry with continuous recording we provided experimental evidence that all three hydroxy acids investigated (i.e. L -(+)-lactic acid, S -(+)-mandelic acid, and R -(−)-mandelic acid) undergo continuous chiral conversion. From the thin-layer chromatographic results obtained it was apparent that — similar to the spontaneous and instantaneous peptidization of amino acids — the hydroxy acids investigated also undergo easy condensation to form the respective polyacids. 13 C NMR spectroscopy provided additional experimental confirmation of this.