Non-covalently bonded diastereomeric adducts of amino acids and (S)-1-phenylethanol in low-energy dissociative collisions

Abstract

We have studied the collision induced dissociation reactions of proton-bound diastereomeric adducts of S-1-phenylethanol and enantiomers of three different amino acids (tryptophan, phenylalanine, methionine). In all cases, the loss of S-1-phenylethanol from the adduct ion is the only observed process, and the relative abundance is found to be independent of the chirality of the amino acid. This is in contrast to earlier experiments on the dissociation of protonated tryptophan–2-butanol adducts, where chirality affected the results. Results obtained from quantum chemical computations support and provide a rationale for the experimental observations and highlight temperature as a possible factor of importance for the chiral effect in these types of systems.