Selective adsorption and reactivity of dipeptide stereoisomers in clay mineral suspension

Preferential adsorption of dipeptide diastereomers (dialanine, Val-Ala) on clay mineral surfaces was observed. Significantly higher adsorption of dipeptides composed from only one type of enantiomer of amino acid units in comparison to those containing both L- and D-type of amino acid units in their molecules, was experimentally proven. This selectivity was explained in terms of different hydrophobic properties of diastereomers, which are probably controlled by intramolecular interactions between nonpolar and polar parts of dipeptide molecules affected by their stereochemistry. A significantly higher reactivity of stereoisomers composed from the same type of amino acid enantiomers to form amide bonds was proven as well. Theoretical study could distinguish different properties of the diastereomers. The results of the calculations indicate possible effects of molecular stability in the stereoselectivity during the adsorption and reactions of Ala(2) diastereomers.