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Here we report on the gas-phase interactions between protonated enantiopure amino acids ( l - and  d -enantiomers of Met, Phe, and Trp) and chiral target gases [( R )- and ( S )-2-butanol, and ( S )-1-phenylethanol] in 0.1–10.0 eV low-energy collisions. Two major processes are seen to occur over this collision energy regime, collision-induced dissociation and ion-molecule complex formation. Both processes were found to be independent of the stereo-chemical composition of the interacting ions and targets. These data shed light on the currently debated mechanisms of gas-phase chiral selectivity by demonstrating the inapplicability of the three-point model to these interactions, at least under single collision conditions.Graphical AbstractElectronic supplementary material  The online version of this article (10.1007/s13361-017-1796-7) contains supplementary material, which is available to authorized users.

Low-Energy Collisions of Protonated Enantiopure Amino Acids with Chiral Target Gases