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Abstract:
A protonated amino acid can interact in several ways with another uncharged amino acid molecule to form a protonated dimer. In case of amino acids that do not have basic or acidic side chains, the most likely protonation site is the amino group and the then protonated amine can be involved in a pairwise interaction with a neutral amine, a carboxylic acid, a carboxylate group and/or the sidechain of the partner amino acid. Here, we employ gas-phase infrared spectroscopy and density functional theory to identify these pairwise interactions in protonated homodimers of serine, isoleucine, phenylalanine and tyrosine. The results show the influence of the different side-chains on the respective interactions. A charge-solvated structure with pairwise interaction between a protonated amine and a neutral amine is preferred if the side chain can provide additional stabilizing interaction with the positive charge. In contrast, for amino acids where the side chain only interacts weakly with the protonated amine group, a protonated dimer is formed by an interaction between the protonated amine and the neutral carboxylic acid of the second amino acid.
